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Sheryl Sculley, Former San Antonio City Manager, Runner and Author

When Sheryl Sculley was hired in San Antonio to be the new city manager, she was confronted with a variety of issues that had long been neglected. From internet usage to wages, she had huge hurdles to overcome immediately. By the time she left, she had become the face of the police and fire union’s fight with the city over their contract. She joins the show to discuss her new tell-all book about her experience.



Justin Hill: Hello, and Bienvenido San Antonio. Welcome to The Alamo Hour, discussing the people places, and passion that make our city. My name is Justin Hill, a local attorney, a proud San Antonian, keeper of chickens, and bees. On The Alamo Hour, you’ll get to hear from the people that make San Antonio great, unique, and the best-kept secret in Texas. We’re glad that you’re here.


Justin: All right, welcome to this episode of The Alamo Hour. Today’s guest is Sheryl Sculley. Sheryl was the city manager of San Antonio from 2005 until 2019. Under her tenure, there are so many accomplishments that we’re going to discuss a lot about today, but for most of us, who just look around The Henry B Convention Center being redone into what it is today, our Mission Trail, the Mission is becoming a world heritage site. Some of the behind the scenes things include how our government works, and our new contracts for our police, and fire unions. She discusses in her book a lot of these accomplishments, we’re here to talk to her about some of those accomplishments discussed in her book, and her new book, Greedy Bastards: One Cities City’s Texas-Sized Struggle to Avoid a Financial Crisis. Sheryl, thank you for joining me.

Sheryl Sculley: Thank you, Justin. I’m happy to be with you.

Justin: Before we got going, I made sure that we could see some of the books behind you on the shelf that people can know that this is a book tour, and I’m part of your book tour today.

Sheryl: Thank you for doing that. This morning I learned that I just made the Amazon bestseller list. I’m excited.

Justin: That’s awesome. Now, you’re going to be scrolling through, and paying attention for reviews as they come in?

Sheryl: Yes. I’m sure we’ll get a few of those.

Justin: Okay. I start all these with a little bit of background information. Everybody knows who you were, and are, but I don’t know how many people know much about you, I learned a lot about you in the book. Unfortunately, for a lot of us– I moved here in ‘07, a lot of what we heard about you, and learned about you had to do with the public union fight. There was a lot of information put out about you, which was I think a little bit unfair obviously. Let’s give a little bit of background to who you are, you came from Phoenix, Arizona. What was your experience with San Antonio prior to coming out here to work as a city manager?

Sheryl: I was the assistant city manager in the number two position in the city of Phoenix, I worked there for 16 years, watched, and was a part of that city growing, doubling in size, and expanding. We worked on major initiatives for that fast-growing city. Before that, I was city manager of Kalamazoo, Michigan. I actually grew up in the Chicago area, went to school in Indiana, and my first job out of college was with the city of Kalamazoo, Michigan. My husband Mike is from Kalamazoo, and our children were born there. I worked for that city for a total of 15 years, I wasn’t born a city manager although I am the oldest of seven children. My siblings accused me of trying to city manage the family.

I started in a research position, joined the city manager’s office as an assistant city manager, and worked there the last five years as city manager. Then I was recruited to Phoenix. We’ve never been there, but our kids were pre-school age, it was good timing to move across the country, take on that new challenge, so we did. I never thought I’d leave Phoenix, I was in the number two position and hope to become the city manager when that manager left. Then San Antonio came knocking, I did turn down the position the first time it was offered in 2005, Mayor Garza was mayor at the time. They were going through an election. After the election, Mayor Hardberger was elected, he contacted me, and convinced me to come to San Antonio.

I did, I was appointed in the summer of 2005. The hurricane Katrina hit the coast the following week, which perhaps was an omen as to the experience I’d have in San Antonio. I signed a two-year contract, it was a really great experience to work with Mayor Hardberger. He’s a wonderful man, he had never been on the city council. I think for both of us, me being not from San Antonio, being new, the council was looking for an outsider to come in, improve the professionalism of the city government here, develop some big bond programs, and improve their service delivery to the community. Here I am, 15 years later I just retired from city management a year ago. That’s after 45 years in public management, but it’s been a great ride and I’ve loved working in San Antonio.

Justin: You make a joke in your book that– You speak very highly of Phil Harburger who’s been nothing but a nice man every time I’ve met him. He’s previously a lawyer in another life like I am as well, but you made a joke that he did more courting you than his own wife. It wasn’t just he convinced you, there was a lot of back and forth before you finally decided to come over. Then it sounds like baptism by fire straight into hurricane Katrina.

Sheryl: Yes, that’s pretty much the case. Actually, his wife introduced me once at an event and she is the one who said that “Heck, he spent more time courting her than he did me for my hand in marriage.” Yes, Linda is a wonderful person and she, Phil, Mike, and I have become close family friends. They’re wonderful people.

Justin: Good. I’m hoping to get him on the show because he’s got some just wild stories about his adventure stuff he’s done. I ask everybody on the show what are some of your favorite hidden gems in San Antonio, you probably know the city better than almost anybody at this point. What are some of the things in the city do you think, maybe don’t get enough attention, or people should go check out?

Sheryl: Yes. Let me say that you had asked me earlier about the Where I Live Column that I wrote during the COVID shelter-in-place situation this spring. I wrote it because as someone who lives on the Riverwalk, we live downtown and it was just so exciting for me to see more people coming to the Riverwalk and using it for exercising. When we first moved here, I’m an old marathon runner, I would go out and run in different parts of the community and I would rarely see anyone out running in the community. There are so many wonderful places now to run in San Antonio.

The Riverwalk is full of people walking, running, strollers, bicycles, no scooters, but there are even people kayaking on the river. Now the extension to the South through the Mission Reach, all the way to Mission Espada it’s gorgeous and beautiful. I encourage people to take advantage of it to even drive to one of the locations and you can cycle, run, walk the entire length of the Mission Reach without crossing a street, and likewise to the North.

I worked with Mayor Hardberger and others on the Mission Reach extension to the north that goes all the way to Brackenridge Park. It’s beautiful as well, so there are some great spots. Hardberger Park, if people haven’t been there, there’s a gigantic dog area as well for dog lovers, but great places to run there. Government Canyon for running is spectacular and beautiful, so lots of places to get out and about in the community.

Justin: Yes, I think I’ve done all of the Riverwalk and the Mission Reach, but there’s that weird chunk between where you live and King William that I’ve never done. Last show that was somebody’s hidden gem that I needed to go do that chunk, so I learns something every time I asked somebody.

Sheryl: It’s beautiful, yes. It is beautiful.

Justin: Yes, sure. What are you doing now? I know you’re a consultant, but what does that mean and what are you working on?

Sheryl: Yes, I’m working a little bit on consulting, not a whole lot with Strategic Partnerships. They’re out of Austin Mary Scott Nabers is the CEO of that organization. I help them think through with companies that are interested in doing business with cities. Not San Antonio, because I don’t want to bother my staff there, but cities around the state that are looking for help on how to improve different systems and companies that have products that can help them help. I’ve been helping them think through some of those issues and how to put those proposals together in those strategies, but mostly, what I’ve been doing is working on my book this past year.

I’m also probably over-committed on my non-profit work. I did join the Texas 2036 board that’s chaired by Tom Luce and Margaret Spellings, the former education secretary, is the CEO. We’re working on the bicentennial 2036 for the state of Texas, what do we want it to be in that year, in what areas does the state need to improve, in terms of education, government performance, health care, environment, transportation and infrastructure, business development? What do we need to do to be better and that’s been an exciting statewide project. Here locally, I’m still involved with the United Way, working on the International Piano Competition for musical bridges around the world.

I’m also working on the campaign for the renewal of the Pre-K for SA program. Some of your listeners may recall that the voters approved that program in 2012. We implemented that program successfully. We have four schools that educate 2000 four-year-olds annually, and provide professional development for early educators throughout the city and all the school districts and also give grants to private schools as well as public schools to help them expand their early childhood education.

We have outside people that its evaluated success. It’s proven to be very effective for families, and it’s free to the lowest income families in the community so, educationally it’s important to San Antonio more so than ever. Now through COVID and that’s on the ballot for renewal November 3rd, so I’m busy working on that effort.

Justin: Well, you make a comment in your book about how you’re a marathon runner and you’re in for the long haul and it sounds like you haven’t slowed down really since you’ve retired.

Sheryl: Not really full days.

Justin: Before we got started, I said you’re my third Anchovy. The other two actually have commented on this post on Facebook already. You also auctioned off your great sachets full of metals for charities after you retired, what are your favorite Fiesta events?

Sheryl: Well, my favorite is cornyation. I confess I was king anchovy in 2009 at the urging of my friends, Tony Bradfield and Dr. Kevin Black and others and it was a great experience. Probably the most fun I’ve had since I’ve been in San Antonio. My husband Mike managed the green room and we have lots of–

Justin: I want to know what that means. [laughs]

Sheryl: Well, liquid refreshment before, at intermission, and between shows. It was a great time. Those who have participated know, it’s a lot of fun. We raised more than $150,000 for the AIDS Foundation that year. It was a great experience. Had a lot of fun, and all my sachets and there were hundreds and hundreds of metals and we did auction those at my retirement event, and from the proceeds from that event, the auctioning of the Fiesta items and my own $10,000 contribution, we donated a total of $40,000 to the Young Women’s Leadership Academy at San Antonio Independent School District to help those girls go off to college so very, very excited to have done that.

Justin: That’s fantastic.

Sheryl: I know you said that you bid on one of the sachets, but you didn’t bid enough money.

Justin: Well, there was an online bidding process and I think I just didn’t pay attention at the time I really needed to.

Sheryl: Okay. All right.

Justin: We’re going to get into the book, but what was your outfit for cornyation?

Sheryl: Oh, boy. You’ve probably seen it that’s why you’re asking. It was a one-piece red Wonder-Woman, Superwoman outfit with a big royal blue cape, red leather boots that laced up above my knees. It was definitely out of character for me.

Justin: Appropriate for cornyation.

Sheryl: Very appropriate for coordination. We had a lot of fun. Phil Hardberger, Mayor Hardberger even did a voiceover as part of the skit for my opening number?

Justin: Well, good for him.

Sheryl: It was a lot of fun.

Justin: I could talk to you about San Antonio for a whole show, but I want to start talking about your book. I learned a lot about your book. Like I said, at the start, I think my first knowledge or seeing you in the public eye other than articles in the Rivard Report or the Express was this deluge of bad publicity and ads and Facebook stuff about you during the police negotiations. I learned a lot about that process through your book, but let’s just start generally, San Antonio has a different form of city government than a lot of cities. Can you explain how we run our city different than other cities?

Sheryl: We have a council-manager form of government that was adopted by the residents of the community by city charter in 1951. What that means is that the mayor and council members who are elected, and we have 11 elected officials, the mayor is elected at large and then we have 10 single-member districts, so that all areas of the city are represented that happened actually the single-member districts in the 1970s. They serve as the policy directors or the board of directors for the Municipal Corporation, and they hire a CEO to run the business of city local government at their direction.

The city manager functions in that way. I’m responsible to hire and fire all city employees and we have a total of 13,000 city employees. What they asked me to do when I was recruited here was to assess talent, make changes, get the financial house in order, I’m not sure they understood the condition of the city government when I was recruited here in 2005, but it definitely needed a lot of improvement. The city manager functions as the CEO of the Municipal Corporation to run the business to hire staff.

Justin: The alternative to that– You just clicked off for a second we’re back. The alternative to that is just a regular a city council and mayor– Where the mayor serves the role of the CEO?

Sheryl: Well, in a strong mayor form of government, let’s take Houston, Sylvester Turner is the mayor. He’s also the chief executive. The mayor is appointing department heads and staff in that case. The council-manager plan is what’s considered a professional local government system and so I’m not hiring friends of elected officials. There’s no political patronage system. I’m trying to hire the best and the brightest from the community as well as nationally to provide the best service for the residents of the community. Chief Bill McManus was one of the first people I recruited to San Antonio. I considered internal candidates, but in the end, I thought that he would be the best, and I think most residents agree he’s done an outstanding job as chief of our police department.

Justin: He tried to leave at some point and just had to come back it sounds like?

Sheryl: He did he went to CPS for about nine months I told him, I thought that he was too much a cops cop and that he would miss that adrenaline rush constantly and sure enough, he called me that summer and said, “Okay, you were right. I want to come back.” I was able to hire him twice.

Justin: I was surprised. In the council-manager form, Phoenix is the largest city of San Antonio, the second-largest city who has that sort of structure?

Sheryl: Yes, we are the second-largest. Dallas is the third-largest?

Justin: Is that trending one way or another nationally, are more cities moving to the council-manager or is everybody stuck in their ways at this point?

Sheryl: Well, it’s the most popular form of government nationally, more so in the medium and smaller sized cities, so there aren’t as many large cities so if you think about New York, Chicago, LA, San Francisco, Houston those are strong mayor form of government cities, but Phoenix San Antonio, Dallas, Austin, Corpus Christi, El Paso here in the state, are council-manager form of government. I’m a huge advocate for professionalism and as I have discussed with the mayors I’ve worked with here and I worked with four different mayors during my tenure here and a total of 47 different elected officials.

There’s so much turnover that you need professional management for the continuity and yet we take the policy direction from the elected officials but because we have experience at delivering those services and understand what it takes to recruit, to manage, and to service deliver in those specific fields, then if you think about it, we’re a very diversified Corporation. We do everything from policing, to firefighting, to emergency medical services, to building roads, to maintaining parks, to running the libraries, public health departments, social services, municipal court, and then all the backup house that goes with those major corporations. I’m an advocate for professional city management.

Justin: Even more so we have some involvement with our water and our electric that a lot of cities don’t deal with, would that be fair to say?

Sheryl: That’s true. Yes, we own as a city– City of San Antonio owns the San Antonio Water System and owns CPS Energy. If CPS Energy were a private utility, they’d be paying taxes to the city. They don’t pay taxes to the city. Instead, the city is entitled to 14% of gross revenue, and that represents about 30% of the city’s general fund budget. It’s an important part. Then the city manager has charter responsibility to make recommendations on their rates.

We have a division within our finance department that actually studies and works with both utilities, water, and energy to discuss what their needs are. We collectively make recommendations then to city council that decides the rates for both of the utilities. Running a municipal corporation is a big and complicated job. It takes someone who has experience at doing that and understands the fundamentals and also can work within a political environment.

Justin: You talk about being a juggler. Now we’re starting to get some sort of context to that. I think it’s important to understand how the city manager is a CEO in the context of your book. Let’s talk about your book. What was the reason for writing the book?

Sheryl: Well, for all the social media coverage that there was about the public safety challenge that we had that is remodeling those 1988 contracts. I felt as though the main point of that was largely still misunderstood. We did this for the residents of the community. I had done some analysis financially with my team to show that left unattended, if we let those 1988 contracts continue as they were, they were crowding out other public services, our street maintenance, parks, libraries, all of those other things that we do as a city because their expenses were growing faster than our general fund revenue.

We did what was somewhat academic, but an analysis to show, when would public safety become 100% of the general fund? When would we turn off the street lights not mow another park, not repair another pothole or any of those other services that we do? Close all the senior centers close all the libraries and it was 2031. It was to say that we need to adjust course, remodel the business model, and to adjust those contracts while still providing a fair salary, wage, and benefit package for our public safety personnel. It’s a core business of the city and I highly regard their work, but it also has to be affordable to the taxpayer.

I thought it was important to also set the record straight here’s why we did this and we were successful. We did get to remodel those contracts. I just didn’t know it was going to take six years to get to conclusion. I knew it would be hard. I thought we could get it done within about two years instead it took much longer. My book talks about why I was recruited here, what I faced when I got here and I tell some stories about some of the things that happened. Then talks about taking on the challenge of these public safety unions.

I have to say it was a hardball experience. Trying to change what had been in place for 25 years when we started this process back in 2014 was difficult. I think the title of the book reflects that, but I can’t take credit for the title

Justin: We’re going to get there in a second. I want to make sure people understand that your book is– I expected it to be a lot more just about the union fights. You walk through hell when you came in, you were given a list of 300 people who are misusing their computers, and it was just you walked through all of the changes you had to make from internet use policies to personnel policies, ethics reform. They had bought a big contract for financial reporting and it wasn’t being used. Corruption.

One thing that really stuck out to me is when you got into the city manager position, you realized that a lot of people were living under the poverty level by which they were entitled to government benefits and people were foregoing some benefits so that they could get government benefits. We had full-time government workers working for the city who were qualifying for federal welfare benefits or welfare type benefits. Talk to me about how you did an analysis to make sure that they had a living wage and you had to make some changes on that.

Sheryl: Well, in the first six months that I was city manager, and this happened in early 2006, as I studied the city’s financials and you mentioned financials, yes, I couldn’t get a financial report from the finance department for the first nine months I was here. I almost quit over that. Instead, we went to work to get that corrected and we did and became one of the best financially managed cities in the country earning AAA general obligation bond rating from all three of the major rating agencies.

I also in that process of going through our city financials found that we had 900 city employees earning below the federal living wage. They were opting out of healthcare from the city and then joining the state-subsidized system, the chip system. I thought that was atrocious. I just moved everybody up. I moved them up to the minimum federal living wage, required all the employees to be on the city’s program and not on public assistance. Over time and in large part, driven by city council members who felt we needed to move up the living wage to eventually get to $15 an hour, we developed a plan to be able to do that in small amounts over time. Now the least a city employee earns is $15 an hour.

Justin: Is that tagged to anything? Is it going to automatically increase as well as cost of living increases or will it have to be a vote each time?

Sheryl: No, it would have to be voted at this point because $15 is still more than the federal living wage amount. It’s above that. If you think about it, we have city employees, families of four living on that type of wage, which is about $30,000 a year. That’s still, that’s still tough, but I’m proud of the fact that we were able to do that for our city workers. It was also about attracting and becoming an employer of choice. I talk about this a little bit in the book that we don’t want to be the last resort for someone, “Oh, I’ll go take a job with the city. They don’t pay well, but I’ll go work there.”

We want to be an employer of choice to take care of our employees, to have them participate, and why we’re doing what we’re doing for the residents of the community and treat them fairly. I think we’re turning it around. There’s still work to do, but we’ve made it better for sure.

Justin: I own and run a small business and I got a lot out of reading your book and the way you went about training and retaining and growing talent within your own organization. I think Eric Walsh said that. That the way you did and went about it was similar to the Popovich and the Spurs organization that you all tried to bring in good talent, but then also train them and make them better as you went on so that when you left, you had a really good talent pool. I found a lot of that really useful just for a small business owner. Did you learn that through schooling or was that a Phoenix thing or was that Sheryl Sculley?

Sheryl: Well, I think throughout my career, I strongly believe in growing people within the organization to take on greater responsibility, identifying them and giving them a chance to grow, but you need to help them. Let’s take, for example, a crew leader in a maintenance area within the city organization. Perhaps the best crew member is the person who gets selected to be the supervisor, but they don’t have any training about how to supervise, how to manage time and sick leave, and someone who’s making mistakes and disciplinary processes and data to manage how well they’re doing. That is productivity analyses.

We developed a first-line supervisory Academy, so that those who were the best workers in a group could also learn how to supervise the crew that they were now in charge of. That’s at all levels of the organization, even for professional staff who maybe then promoted to supervise a group of planners or a group of engineers, how do you manage people? Because we spend most of our time managing people to get the productivity we need to be most effective. I also found that at the executive level, we really didn’t have a deep bench.

There were good people within the organization, but they weren’t in the right seats on the bus as Jim Collins famous author would say. I moved people around into positions that they were best suited for and identified people within the organization like Eric Walsh, like Maria Villagómez, like Ben Gorzell, and Rod Sanchez, to move into positions where they could be most effective and grow. It was a combination of recruiting from the outside in the areas where we didn’t have internal talent to take on specific departments and assignments but also working within the organization to grow.

When I was recruited, they wouldn’t consider someone inside the organization. That was a red flag to me. I knew from the beginning that my job in part would also be about developing staff so that when I chose to retire that they the council at the time had choices. There were a variety of people that could become the city manager. I’m proud to say that all six of my deputy and assistant– Sorry about that. All six of my deputy and assistant city managers applied for the job were interviewed, and they selected Eric, my deputy, as my successor. That’s exciting to me and gives me a sense of accomplishment.

Also, the city manager in Dallas is one of my former assistant city managers, TC Broadnax, and Peter Zanoni. Another one of my deputies is now city manager in Corpus Christi and Penny Postoak Ferguson, an assistant city manager, is now the county manager in Johnson County Kansas. There are San Antonio members of the executive team who are now out there as city managers elsewhere around the country. That makes me proud as well.

Justin: Like Pop’s coaching staff, they’ve gone out everywhere as well.

Sheryl: That’s what Eric said. I don’t know if I deserve that comparison, but I’ll take it.

Justin: Yes, of course. [laughs] Okay. I want to talk to you about the union contract. There’s a lot of things in your book that really surprising to me, obviously. I knew there was an issue with the longterm viability of the costs of it. Talk about when you came into the position. You came into the position after you turned it down, long time courting. Based on your book it sounds like there had been some council members who had been indicted prior to you coming over. Things were a little bit of a storm maybe to walk into. Then at some point, people said, “Hey, you’re going to have to start taking a look at this contract.” Was it a fire off in the distance or was it coming up pretty quick?

Sheryl: Well, actually they were in negotiations with police and fire when I was hired, but I had so many figurative fires to put out that I could not devote my entire attention to that in those initial months. Those contracts were wrapped up and they were coming due then in 2009. By 2009, I had a pretty good handle on the city organization and I knew we needed change. The healthcare benefits, and you’ll understand this, we were covering almost 100% of healthcare for our uniform personnel, as well as their spouses and dependents. In 2014 when we were finally taking this on as a challenge, that number out of the cost to the city had grown to $20,000 per uniform. We have 44,000 uniforms, so $20,000 per uniform.

When I talk with business groups about that to explain why we were taking on this challenge to remodel, and it wasn’t about just cut their benefits, it was about how do we provide a consumer-driven healthcare plan with high deductibles for those to choose. If you wanted the legacy plan, then you paid a premium for your dependence. We still cover 100% for the police officer and firefighter.

Justin: Which is almost unheard of anymore.

Sheryl: We had to get those costs under control. What?

Justin: I said that’s almost unheard of anymore in a lot of places for that legacy plan to be funded 100% because it was a Cadillac plan.

Sheryl: Yes, and it’s 25 years old. I’m not passing judgment on what was decided back in 1988. I wasn’t here then, but it’s not affordable today and it’s clearly not sustainable. They were bankrupt, the city. In fact, most business people when I had explained this would say, “Gosh, I’ll be bankrupt if I provided that.” Well, that’s my point. I wanted to take it on in two– I apologize. For some reason, my cell phone is coming through on my iPad. It doesn’t normally do that. Probably because I had my phone turned off

Justin: They’re very popular right now, high seller, top selling on Amazon. It’s going to make your phone ring.

Sheryl: [laughs] I wanted to take it on in 2009. The mayor and council were reluctant. In part, I believe, because the unions in the past had intimidated them by saying, “If we don’t get what we want, we’ll run a candidate against you.” I’m simplifying it, but that’s in essence what had happened over the years. They said, “You can try. We understand why you think it’s necessary to do this, but you’re pretty much on your own at doing it.” Of course, the unions went around me to the council, and eventually, the council said, “Just settle it. Give them what they want.’

At the time Major Castro was just newly elected as mayor. Phil Hardberger had been termed out. He could only serve four years. Mayor Castro said, “I have some initiatives I’d like to work on that are very important first, but I commit to you that we’ll come back to this and work on it.” The unions had a five-year contract that would expire in 2014. In 2013, I sat down with the mayor, my team and I, my finance and budget director, and I sat down with the mayor and said, “Here’s the business case. We’re taking this on and making change.” Mayor Castro agreed and supported our taking this on and said, “Okay, city manager, I what you out front on this issue and we’ll stay together as a council.”

I discussed it with the mayor and council. They all agreed we should do this, and we did. The unions liked me until then, but once we took this on that whole thing changed. They really tried to portray what we were doing as anti-police. I’m not anti-police. I’m not anti-fire. It is our core business, as I said, and it’s an important part of what we do, but it has to be affordable to the taxpayers. We did this for the community. We stayed the course. We did mediate a settlement, of course, with the police union in 2016, and then an arbitrator made the final decision of what we had recommended just in February of this year.

That arbitration process started a year ago after the unions ran a candidate against mayor Nierenberg hoping that their candidate would win and convince the council members to give them what they wanted. Fortunately, he lost. They filed for a binding arbitration and it didn’t work out too well for them. In total what’s most important is that the city is saving more than $150 million just during the five-year term of these two contracts with what we were able to do. Then those are changes longterm for the city.

Justin: Your book does a good job. This wasn’t willy-nilly. There was a lot of analysis that went into it. You walk through the medical costs were basically unsustainable over the longterm. They had a legal defense fund. It almost sounds like it was being used as a slush fund with very little oversight. On top of that, it sounds like there was instances of abuse where people were using the free legal fees to have family fights on the taxpayer dollar. There’s discipline issues, the me-too clause.

Then you get into some of the more strange stuff, the 100% tuition reimbursement where people were going back and getting degrees for things that had nothing to do with their job. There was no oversight on that. Then cops were being given a bonus for having their certificate that they had to have to be an officer. There was a lot of strange pay benefits and awards worked into these contracts that once you started really parsing apart, you realized this is unsustainable longterm, but they are also just some things that don’t make sense from an equity standpoint. Would that be fair to say?

Sheryl: Yes, very much so. In the oversight, we had no authority on oversight because the collective bargaining agreement provided, for example, the legal fund that to pay for police and fire officers wills, estate planning, divorces, child custody disputes, criminal defense if they or their family members were picked up for a DUI, the contract specified that the city contributed about 1.5 million a year into that fund. 

Interestingly, that fund, of course, was put into place back in that 1988 contract. There were some things, some bribes that were taken as a result of that by the Police Union President at the time, Harold Flammia. He was indicted, went to prison, for that legal fund. What city provides legal defense for criminal activity or pays for officer’s divorces?

That was then, this is now. I thought that needed to go away. If they wanted to contribute themselves to a fund out of payroll deduction, that’s fine, but I didn’t think the city should be paying for that. There were a lot of things controlled in that contract that really needed to change and the process for discipline is another one and that we– [crosstalk]

Justin: Which still has to be dealt with.

Sheryl: It still has to be dealt with and in this next contract because it was a priority for us, it was among our list of things we want to change. Revising the healthcare model, and also changing and putting some guidelines in place for tuition reimbursement being applicable to someone’s job and on a matching basis, for example, eliminating this legal fund, but the discipline we did not get. I think the mayor and council, even the community had grown weary of the fight. It was ugly and pretty vicious-

Justin: And long.

Sheryl: -and long, and became personal, but they did that to try to really villainize me that I was anti-police, which wasn’t the situation at all. In any event, we were doing this to safeguard the future of the city’s financial position, and we wanted the chief to have greater authority in being able to discipline bad officers and he doesn’t have that full authority today, he needs to have it. That’ll be I believe a priority in the next contract, or it certainly should be.

Justin: Is there a reason you think y’all were able to come to a mediated agreement and settlement with the police union, but not the firefighter’s union? Were the negotiation tactics different? Was there differences to the contract that made it more viable or was it a personality issue?

Sheryl: Probably mostly a personality issue. When we reached the mediated settlement in June of 2016, we had asked the courts to order mediation. When both unions wouldn’t come to the table and negotiate anymore, we filed a declaratory judgment action, a Dec Action, asking the courts for a ruling on constitutionality of a 10-year evergreen clause. Their contracts also had a 10-year evergreen clause. After the five-year contract ended, the terms and conditions continued for another 10 years or until you were able to negotiate.

Now, I come from a labor family. My dad was a union member and leader. I worked in Michigan, one of the toughest labor States in the country. I have some experience in this area and I’d never seen– A 10-year evergreen clause? Come on. That was tying the hands of the city council that they couldn’t make financial decisions beyond even when they’re serving because they have eight-year term limits to serve as council members.

We thought to get them to the table, the risk of losing that completely if the courts decided it was unconstitutional, would get them to the table to negotiate. Instead, they doubled down and then started running those expensive TV ads against me. There were many people in the community who said, “We need to run our commercials against them.” I said, “No, that’s good money after bad, we’re not– Just stay focused. We’ll ignore it.” Of course, I didn’t realize it was going to go on for years, but when you say, “Someone’s bad. Someone’s bad. Someone’s bad” Eventually, people are like, “Gosh, they must be bad.”

Justin: Yes.

Sheryl: There was some of that going on, but the courts then ordered mediation, circuit court. I knew, I told the council, I thought the lower courts would probably rule against us. It made it very difficult for them, they too are supported by police and fire. I thought our best chance was to go to the Supreme court, but nonetheless, we were able to mediate a settlement with the police union. The Fire Union actually tried to campaign against that when it had to go to the vote of the police officers because they thought that the police union had given way too much. I thought we left money on the table. I wanted to get the disciplinary changes, but in the end, it was ratified by their membership and the city council approved it. We were done. Then, the fire union just refused to negotiate.

Justin: I was doing some research into Harold Flammia. I’m sure you have heard the backstory more than I could ever hear, but it sounds like he was one of the first union presidents to put the police officers into a political pack and really flex their political muscle. It sounds like that was how he was able to create this just really advantageous union contract because he created a pack. He started taking in money monthly. He created a big fund and he flexed that muscle. Is that the backstory on how that contract came to be in the late ’80s?

Sheryl: I think you’ve summed it up pretty correctly. He had been an officer who was shot in the line of duty. He had multiple surgeries to correct and improve his health, and he wanted more for the officers and I understand that, but it has to be affordable to the taxpayers. Yes, they do flex their political muscle. In other States, especially common among the council managers form of government city employees, are not allowed to work on campaigns.

In Texas, police and fire can work and endorse candidates so elected officials seek out their pack and endorsements by those unions. That’s the rub. They have a book that their chief negotiator put together. It’s entitled Union Power, Politics, and Conflict in the 21st Century. It’s basically about how to fight city hall if they try to change wages and benefits.

Justin: It’s reminiscent of Roy Cohen, the way he taught political leaders in the Northeast, including Donald Trump to attack. He had a playbook by which he went about people that disagreed with you. I was reading something about that book before you came on the show today, and it’s very much like attack, escalate, and make it really uncomfortable for everybody. One interesting point is that book had a chapter by Harold Flammia that was removed in the second edition after he had been prosecuted or pled guilty to the felony.

Sheryl: That’s correct.

Justin: Yes, it was pretty interesting.

Sheryl: The book itself also talks about escalation is key. You have to escalate and even fight cities when they try to propose bond programs, that that’s a way to get their attention. Tell the elected officials that they will oppose the bond program unless they get what they want in their contracts, and because they have money and they’re organized. They have the ability to do that.

Justin: I want people to read your book and I want them to get a flavor for all of this that they don’t understand because we saw enough of it in the news, but if it’s okay I want to pivot a little bit and I want to talk to you about– You had to show such poise and also control to not fight back. Talk to me about some of the leadership qualities either you used, or you learned in that big, public, and nasty fight.

Sheryl: If I had to do over, I would have developed a more comprehensive communication plan that could be used for the public. It was a bit developed as we went through the process. I would have done that upfront, had it adopted by the city council and then been able to follow that more closely. People would ask me to speak about– Because the unions were putting out so much misinformation, they’d ask for, “Okay, what’s really going on?”

I would explain it and they’d say, “Well, why don’t we know that?” I started, for example, a letter that was going out to people who were contacting me asking, that would go out monthly to say, “Here’s where we are, here’s what’s happening.” It grew to about 500 people because so many people were asking about that. We should have been, I think, better organized in that regard.

Now, one other thing, that I did do. Previous to my being here in this position in San Antonio, they had negotiated these contracts in a conference room at the lawyer, the labor lawyer who represented the city in his conference room. In Texas, because we’re right to work state, if you have collective bargaining negotiations, which are permitted under the local government, the Texas Local Government Code, it has to be open to the public. I’m sure they posted it when followed the letter of the law, but who’s going to find the law office and the conference room [unintelligible 00:50:30]

I knew that we’d have to have a public discussion because they had these contracts for 25 years and so we needed to educate the public as to “Here’s what’s in, here’s what we’re trying to change.” I brought the negotiations to city hall and we invited the media and my public information director, Jeff Coyle, a former news person himself from the private media, he would meet with the media, I had a time to say, “Here’s what we plan to cover today. Here’s why.” Because with TV, they get a sound bite and they leave and they don’t understand at all. The unions objected to that, they viewed that as throwing down the gauntlet that we were saying bad things about them, not at all.

What we were saying is, “Here’s what exists today, here’s what we’d like to change. Here’s how we’d like to go about it, we’re very methodical about it,” but instead, that’s why they went after us. What I learned in this process, there was so much media and social media, became a problem as well. The unions had trolls that would follow any positive comments and then have five or 10 negative comments dumped on it. It was all very organized. I told my staff, “We’re not going to read all that stuff, we’re not going to follow it all, we’re going to stay focused on what we want to do. Educate those in the community who need to know most about this, our elected officials, and those in leadership positions and stay the course ignore that.”

While this was going on, this was one aspect of my job. I was still running the city operations for the entire organization and so all of that negative stuff can really bring you down. I said, “We’ve got to keep our heads on straight, stay focused on what we’re trying to do. We will stay the course.” I’m sure my family would say that I come home at night and just be like, “Oh my gosh, how much longer can we do this?” We had to put on a strong public face and I needed to stay strong for my team.

We’d collectively together decided this was important to do. I felt that because I was approaching the end of my city management career. I worked for 45 years in public city management. I could take this on and it would be the final financial legacy I’d leave for the city, changing the financial models of these contracts. Those were some of the things I learned in the process.

Justin: Because of their political influence, and because of the fact that our city council and mayor turnover a fair amount, you’re left leading this fight because you didn’t have to worry about running for election. If the city was to do this again, can you think of a better way for it to be done so that maybe our electeds aren’t as worried about the force of the union and also so that there isn’t one person like yourself who’s stuck carrying the water on a contentious issue?

Sheryl: I think there has to be agreement upfront between the city manager and the mayor and the council that we’re in this together. Not that everyone will be unanimous in how to go about it. If you have elected officials who don’t have experience with labor unions, and let’s face it, we’re in a right to work state,4 so most of the elected officials in San Antonio, unless they were part of companies that had union employees and other places and knew what it meant to deal with collective bargaining, really don’t understand the magnitude of it.

Oftentimes, I would hear from newly elected officials, “Can’t we just settle this? Can’t we just be nice and settle this?” The unions were clearly not being nice about it, they didn’t want anything changed, they said that or they said as much when we began the process. I think there has to be more alignment and participation by the elected officials to stand behind the executive staff as to here’s what needs to be done.

I had tremendous support from Mayor Nirenberg and the unions, of course, then ran a candidate against him in the last election. In the end, something I learned very early in this career and I learned it from my father, you have to do what’s right, do what’s right. If it means that you’re not reelected, and that’s hard for elected officials to face that, then so be it. There’s an old saying, “Always do right, it will satisfy some and astonish the rest.” We did this and I dedicate the book to the residents of San Antonio. We did a lot together and we did this for them.

Justin: You’ve got a quote by Robert Rivard in your book about it. I’ve had people reach out to me, I was told that before you got here is real backslap and good old boy. How much of the attacks from the unions and the police and fire do you think were related to the fact that you’re a woman?

Sheryl: I think quite a bit. I think if I were a man and from San Antonio, they wouldn’t have treated me this way.

Justin: The attacks got particularly personal almost. It was an attempt to attack you in all ways.

Sheryl: Yes, they were. They were extremely personal, very sexist. Think about it. Our departments are 90% men. I know in the first negotiating session with the police department, the labor team included three women, two attorneys, and my HR director, all women. The men asked for where’s so and so who negotiated the last contract and they said, “We’re here to negotiate.” They caucused, never came back that day. They weren’t just rude to me, they were rude to the women who were on our team entirely. No, I don’t think they would have done this to a man, not at all.

Justin: Advice for women who are dealing with similar things or advice for women who feel like they’re going to face that if they take on a contentious issue.

Sheryl: Thick skin, grow it.


You have to do that but also have a support system. I didn’t do this on my own. My team and I sat down and said, “I think we should take this on.” We discussed it thoroughly. “Are we all on board?” We supported one another. We were a tight-knit unit working on this together with mayor and council support. It was tough to take on, but in the end, we were successful and that success will be reaped by the residents of San Antonio.

Justin: First book to write or you write another one?

Sheryl: [laughs] Not right away.


I have been asked already, “Hey, we have ideas for another book,” but no not right away. I want to fully discuss this. I hope it’s a history lesson for the residents of San Antonio, but also can be used as a guidebook for other city managers, elected officials, and communities across the country that are facing some of these very same challenges because this could be any city, USA.

Justin: It’s great to read it, to track how the city changed over the last 15 years. The union battle is part of it, but it’s– Honestly, I didn’t find it overwhelming at all. It wasn’t a book about a union battle, it was a book about changing a city. For people like me, it’s changing in the ways of “Oh, I’ve been to that park” or “I know what Pre-K 4 SA is.” I thought it was really interesting just to get that background of the history. Your book tour will continue. I think you and Robert Rivard are going to do a second run at a question and answer, is that Friday?

Sheryl: It is tentatively scheduled for Friday at 11 AM. I think he’s working through some of the technology issues because the site went down yesterday about halfway through the program. Maybe it’s because there were so many people that had registered for the event. I’m told there were more than 800 people-

Justin: That’s great.

Sheryl: -on the site. There’s an awful lot of interest and of course, the books available in hardback, paperback, and in the electronic version on Amazon.

Justin: It’s available on Amazon. You mentioned something if somebody wants to get a– First of all, all the proceeds go to charities. Then if you want a signed copy, how can somebody get a signed copy?

Sheryl: Yes, you can either contact me if you know me, if we know each other, please contact me, but The Twig Book Shop at The Pearl has signed copies. I’ve been madly signing hundreds of books and we’ve delivered several hundred to them already that are already committed but we have more. I’m happy to sign a book, just contact The Twig.

Justin: Sheryl, thank you so much for doing this. Thank you for writing the book. It gave me so much background into a city that I really I love, and honestly, I didn’t start paying that much attention to local politics until the union fight because it was unavoidable. It was on billboards, it was TV, it was social media, so it kind of awoke my interest in local politics. Thank you for giving the background in this book, and I enjoyed the read, so thank you for doing this. Good luck on your book. I hope it sells a ton of copies, and once COVID is over, I hope you’ll let me buy you a drink and shake your hand and say, “Thank you so much.”

Sheryl: I’ll take you up on that. Thank you, Justin.

Justin: Okay. Take care. Be safe.

Sheryl: Bye-bye.

Justin: Bye-bye. All right, that’s going to do it for this episode of the Alamo Hour. Thank you so much to the former city manager, Sheryl Sculley for joining us and talking about her book and her experience. I encourage you to read the book. It’s got a whole lot of background in history about San Antonio over the last 15 years. You hear a lot about the players, you hear a lot about the backstories on a lot of different things that we take for granted in the city. Our wishlist continues. I’ve reached out to Phil Hardberger. I hope I can get him on. I mean, the guy flew a single-engine plane across the Atlantic, raced a sailboat, and was largely responsible for getting Sheryl Sculley to come join our city. Until next time, thanks for joining us, and we’ll see you on the next episode.

Thanks for joining us on this episode of the Alamo Hour. You are what make the city so great. We hope you join us next week. In the meantime, subscribe to our podcast and check us out on Facebook slash/alamohour or our website, Until next time, Viva San Antonio.


[01:01:51] [END OF AUDIO]

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