At the turn of the 21st century, downtown Orlando was foundering. The Church Street district, once a bustling tourist attraction straddling the railroad tracks, had become a ghost town, overshadowed and outperformed by Downtown Disney and Universal’s CityWalk. Orange Avenue, Orlando’s main street, was dotted with dilapidated buildings and vacant storefronts. Among the biggest eyesores was the so-called Jaymont block, an empty block of stores along Church Street and south Orange Avenue that the Orlando Sentinel reported had turned into “termite-and rat-infested homeless camps.”

“Orange Avenue was a disgrace,” recalls John Morgan, the well-known Orlando trial attorney who’s had an office on the street since 1985. “It was a city in decay.”

Two decades later, the former Jaymont property has been replaced by a mixed-use development that includes two office towers, ground floor retail and a 12-screen movie theater. The city is now home to world-class sports and entertainment venues, including the Amway Center (where the NBA’s Orlando Magic play), the Exploria Stadium (home to the Orlando City Soccer Club) and the Dr. Phillips Center for the Performing Arts. With the recent completion of the SunTrust Plaza tower and a second skyscraper in the works, the Church Street district is finally getting a makeover.

At the center of the revitalization is John Hugh “Buddy” Dyer, the 61-year-old Democrat who’s Orlando’s longest-serving mayor. His political acumen — and the ability to serve for more than 17 years — has helped him get a lot done. Orlando is one of a few cities in Florida without term limits for mayors, allowing Dyer to stick around long enough to advance the ball on important civic issues and signature development projects. “I’ve seen Orlando pre-Buddy and I’ve seen Orlando post-Buddy, and that’s a gigantic difference,” says Morgan. “Orlando, Florida, is the city that Buddy Dyer built.”

From cattle to campaigns

Dyer was born in Orange Memorial Hospital, now Orlando Regional Medical Center, and grew up in Kissimmee, where his father, a champion bull rider, worked as a cattle truck driver. His mother worked for Tupperware, Vanda and Disney before opening a Western wear shop called The Mod Cowboy that she ran for 20 years. There was little ethnic diversity where he grew up: “I knew one Hispanic kid. You were either a white cowboy, a white surfer board boy or an African-American,” Dyer recalls.

Dyer’s father, Butch, would return from long hauls with a truck full of manure, and young Buddy earned $5 a load cleaning it up. The experience inspired one of his oft-repeated gag lines: “I was shoveling manure at an early age, and it served me well through a legislative career and City Hall.”

Dyer was a high school standout — captain of the baseball team, MVP on the football team and president of the Key Club. He also participated in drama. Though he wore a Harvard Tshirt throughout high school, when it came time to choose a college, he picked Brown University, which he says was “en vogue” at the time.

For the country boy from Kissimmee, the Ivy League experience was eyeopening. Dyer had the highest SAT score at Osceola High School. At Brown, he had the second-lowest score among the freshman who lived on his hallway. It was also a social awakening of sorts. Classmates had surnames like Cartier, Cronkite and du Pont; his teammates on the rugby field included the late John Kennedy Jr. and Brian Moynihan, who became CEO and chairman of Bank of America.

After earning his undergraduate degree in civil engineering, Dyer returned to Florida, landed an engineering job and ran for a seat on the Kissimmee City Commission, where his late uncle Jimmy had served. He lost and eventually went to work for a mining company north of Ocala in Lowell that manufactured kitty litter from calcium-montmorillonite clay. Dyer’s job was to find other environmental uses for the clay, such as lining ponds and covering the tops of landfills. “I was the sales guy. I was the engineer. I was the on-site installer,” says Dyer, who worked there for about four years, saving enough money to attend law school at University of Florida.

Gainesville is where Mayanne Downs, former managing partner and a shareholder at Gray Robinson, met him. “We were all active in the law review, and there was a contested election for editor in chief,” Downs recalls. She approached Dyer to let him know she “had some information” about his opponent that she thought would help him win. It did — and began a lifelong friendship between the two, who both returned to the Orlando area to start law careers and raise families. “He likes to say sometimes I was his consigliore in his very first election,” Downs says. Dyer named Downs Orlando’s city attorney in 2007.

Dyer dove into state politics in 1992, when he won an open seat in the Florida Senate. He was working as a lawyer for the Orlando firm Winderweedle, Haines, Ward & Goodman, while his wife, Karen, was building her own law career at Carlton Fields. With Karen on the road a lot, Dyer would take their toddler, Trey, with him to Tallahassee when the Legislature was in session. “That kind of kept me grounded,” Dyer says of his Mr. Mom era. “I was the youngest member of the Senate at the time.”

In Tallahassee, Dyer earned a reputation as a pro-business Democrat with friends on both sides of the aisle. He rose through the ranks to become Democratic leader from 1997 to 2000 and points to the Lake Apopka Restoration Act in 1996 as his favorite legislative accomplishment. The legislation allocated $100 million over three years to buy phosphorus-discharging farmland along the northeast corner of the lake that was contributing to pollution.

Over the course of Dyer’s decade in Tallahassee, he built a base of support back home that included police and fire unions and various civic groups. A regular presence in Orlando’s African- American churches, Dyer also developed a constituency among Orlando’s black voters — and earned the trust of gay voters by voicing support for a 2002 anti-discrimination ordinance designed to protect gay and lesbian people from housing and employment discrimination. Business interests like him, too. Associated Industries of Florida, a business lobby, ranked him as the state’s “most business-friendly senator” in 1993, according to the Orlando Sentinel.

Over the course of Dyer’s term, however, the Democratic Party lost its grip on power, and in 1994, Republicans won control of the Florida Senate for the first time in a century. Forced out of the Senate by term limits in 2002, Dyer ran for state attorney general against Charlie Crist, then a Republican, who’d also served in the Florida Senate and done a two-year stint as education commissioner under Gov. Jeb Bush.

Dyer garnered more editorial page endorsements than Crist but struggled with statewide name recognition and couldn’t match Crist in fundraising. Stumbles by the Democratic gubernatorial candidate, Tampa attorney Bill McBride, also hurt Dyer’s bid. “Our model showed (we would win) as long as McBride didn’t lose by more than 10,” Dyer recalls. In the end, McBride lost by 13 points, and Dyer lost by about seven.

After the loss, Dyer figured he’d return to practicing law full time, until Bush appointed Orlando Mayor Glenda Hood as Florida secretary of state.

“Being mayor of Orlando was nowhere on my radar, hadn’t been in my life plan or anything like that, but a lot of people started asking me about running,” Dyer recalls. Seven candidates had lined up to campaign for the job because Hood had already announced she wasn’t going to run for re-election. But the police and fire unions who’d gotten to know Dyer as a senator wouldn’t endorse a candidate until he decided what he was going to do.

An early morning call from Sam Green — a pastor at the local Saint Mark AME, Orlando’s largest African-American church — cinched his decision. Green told Dyer his prayer group thought Dyer the “only one who can unite the city, who is able to walk on the west side and in the boardrooms in the east side,” according to Dyer, and urged him to run.

After consulting with family and friends, Dyer decided to run. “I didn’t know much about being mayor of Orlando at the time, but with eight people in the race, we had all these debates,” Dyer recalls. “I learned a lot in five weeks.”

Dyer won the February 2003 election following a runoff and hit the ground running. Taking a page from former New York Mayor Rudy Giuliani’s playbook, he organized a Cabinet-style government, with his department directors acting as his Cabinet. He held meetings with them twice weekly to get a handle on what everyone was doing. And he borrowed former Florida Gov. Bob Graham’s workday program, shadowing city workers on the job.

Facing a $24-million budget deficit, Dyer laid off more than 200 city workers and began to work on delivering his campaign promise to revitalize downtown Orlando. Dyer had talked to developer Cameron Kuhn about buying the blighted Jaymont block from Tavistock. Kuhn liked the idea and came up with a plan for a $140-million development that included office towers and a movie theater. To seal the deal, the city offered Kuhn $22 million worth of incentives.

Dyer worried preservationists might stand in the way of Kuhn’s efforts to demolish the Art Deco buildings that had housed a Woolworth’s and a McCrory’s dime store. He let them have their say at a city council meeting that ended with a 5-2 vote to demolish the block but didn’t wait to see whether they’d fight on. Immediately after the vote, demolition equipment that had been positioned at the fire station rolled down Orange Avenue and razed the buildings along the Jaymont block before the sun came up the next morning.

The move angered some, but Dyer makes no apologies. “It didn’t give anybody an opportunity to go into court and get an injunction,” he says, adding that it “gave the business community the message that we would use our political capital to make sure that things got done in downtown.”

As the Jaymont block was redeveloped, Dyer turned to bringing a performing arts center to Orlando. It wasn’t a new idea. Former Orlando Mayor Bill Frederick had planted the seed in the 1980s, and Hood had also tried unsuccessfully to push the project during her 11 years in office. Dyer renewed the push but took a different approach. As he mapped out a plan, “it became clear the Citrus Bowl was a dump, and it needed a renovation and the Orlando Magic needed something done with the (Amway) arena,” Dyer says.

He suggested bundling all three projects into one package to induce cooperation from competing interests: Sports supporters and arts boosters would have to support each other if they wanted their pet projects to succeed.

There were other hurdles to overcome, including opposition from tourism industry leaders who didn’t want to share bed tax dollars with the $1.1-billion sports and entertainment venues. Dyer worked with then-Orange County Mayor Richard Crotty (his predecessor in the state Senate) to broker a deal that would let the county implement a penny bump in the tourist development tax, with a half-cent of the hike going to the arena and half going to tourism marketing to help hoteliers. To foot the rest of the bill, Dyer tapped funding from the city’s Community Development Agency bonds, corporate and philanthropic contributions, state funding and other sources.

Although the 875,000-sq.-ft., city-owned Amway Center opened in 2010 as planned, the 2008 recession slowed the other two projects. By 2011, a shortfall in tourist development tax funding had stalled the Dr. Phillips Center for the Performing Arts, and Crotty’s successor, Teresa Jacobs, lambasted the project in a letter to Dyer that detailed a number of “serious financial and construction-related concerns” uncovered by a county review of the project. That sparked a clash between the two mayors — with each telling the media they didn’t trust the other.

Dyer and Jacobs eventually settled their differences, and the arts center was finished in two phases, the first completed in 2014 and the second scheduled for completion this fall. Renovations of the Citrus Bowl, now known as Camping World Stadium, were scaled back — but Dyer says he’s pleased with the $200 million in upgrades that were finished in 2014, and the stadium is set for another $60 million in upgrades to help the venue compete for the chance to host the 2026 FIFA World Cup. “I think we did pretty well for $200 million. It’s an NFL-quality stadium. Everybody else has spent billions on theirs,” Dyer says.

Other milestones under Dyer’s watch have included the 2014 launch of Sun- Rail, Central Florida’s regional commuter rail system; the establishment of Medical City at Lake Nona; and securing a Major League Soccer team and building a privately funded soccer stadium. The city’s latest landmark was the 2019 opening of a University of Central Florida/ Valencia College downtown campus, which is part of the public-private Creative Village project on 68 acres where the old Amway Arena stood. Electronic Arts is planning to move its headquarters there next year from Maitland, bringing 700 high-wage jobs downtown with the hope of spurring the rise of a new digital media cluster.

Those who know Dyer describe him as a cerebral, deliberate leader — an introvert who understands how to run a big city and relishes challenges. “I don’t think Buddy was cut out to be a day-today lawyer,” says Morgan. “I believe that being the chief executive of a big city, doing big things — he needs it for his own mental stimulation that he never would have found being a lawyer charging by the hour.”

Heather Fagan, a longtime aide and currently Dyer’s chief of staff, says that once Dyer has a vision for something, he sees it through to completion. “He’s taken on very complex projects that often hit road bumps or hurdles or ‘no’s’ and he never stops pursuing what he thinks is right for the community,” she says.

Fagan cites Major League Soccer as an example. The original plan was for the city and Orange County to contribute about $35 million and get another $30 million from the state — but the state funding never materialized. Fagan recalls riding back from Tallahassee in a car with Dyer and Phil Rawlins (who would become Orlando City team president) after the last day of session in 2015, when their request for funding didn’t even make it to the floor. “It was about an hour of silence, but then the mayor turned to Rawlins and said, ‘Ok, well what do we do next?’ ”

Brazilian businessman Flávio Augusto da Silva, majority owner of the team, came up with a plan: He’d fund the stadium privately — in part with money from EB-5 investors who’d get visas in exchange for their investment — and pay the city for the land. Dyer learned of the new business plan over drinks with Rawlins at the Alfond Inn in Winter Park, where the two drafted a “memorandum of agreement” on the back of the bar receipt, which now hangs framed in Dyer’s conference room in City Hall.

There were other snags. The Faith Deliverance Temple sat in the middle of the Parramore neighborhood where the soccer club and the city wanted to build the stadium, and sales negotiations had broken down. The church was asking $35 million for the property — an amount the city viewed as far above its value.

Meanwhile, eminent domain proceedings the city had initiated against the church property were dragging on, angering many in the community. Orlando Sentinel columnist Scott Maxwell, a sometime critic of Dyer, blasted the city’s push to seize the church property. “This is the Buddy Dyer way. Barge ahead. Don’t seek permission first. Apologize later. Or heck, don’t even do that,” Maxwell wrote in a 2014 column.

During a meeting with architects, Dyer suggested moving the stadium a block west. They agreed to move the facility, and the city made one final offer of $5 million to the church. “They turned it down, and that was the best day (Chief Assistant City Attorney) Roy Payne has ever had, calling them back and saying, ‘You get your wish. You get to keep the church,’ ” Dyer recalls.

Weathering storms

While Dyer has dubbed himself the “happiest mayor in America,” his tenure hasn’t been a cakewalk.

Following his 2004 re-election, his Republican opponent, Orlando businessman Ken Mulvaney, accused Dyer of violating Florida election laws by paying campaign aides to collect absentee ballots. That triggered an investigation that culminated in the 2005 indictment of Dyer and three others, including his campaign manager, a get-out-the-vote consultant and Orange County Circuit Judge Alan Apte. Dyer turned himself in and was booked on third-degree felony charges. Then-Gov. Bush suspended him from office.

“It was probably the lowest point in his life. He came to my office and we gave him a key and (access) to the parking garage, and he kind of based himself out of (Morgan & Morgan) for a month or so,” Morgan says, adding the charges against Dyer were “all B.S.”

Dyer and his defenders said the charges were politically motivated and that no one had intended to break the law. It later came out that Hood and other Republicans had also used the same get-out-the-vote consultant to collect absentee ballots in their campaigns. Six weeks after the indictments were handed down, Florida prosecutors dropped the charges, and Bush reinstated Dyer.

An even more complicated challenge came 11 years later, when a gunman walked into the Pulse nightclub, a popular gay bar on south Orange Avenue, and began shooting.

Dyer was in bed when he received the call from Orlando’s deputy chief of police around 3 a.m. on June 12, 2016. Dyer headed to a command center near the club and began organizing a communication plan. The situation played out throughout the wee hours of the morning, ending with the death of the shooter, who had killed 49 patrons and injured dozens of others.

While the FBI labeled the massacre a terrorist attack and took charge of the investigation, Dyer convinced the bureau he should lead the press conference. He insisted the public needed someone they knew, not an anonymous person in an FBI jacket, to share information about the tragedy.

“He came out of the gate saying, ‘We will not let hate win.’ It wasn’t a bunch of marketing people or a crisis management team who came up with it — that was Buddy,” Downs recalls. “He said it forever, and he still says it. It was just a balm on everyone’s spirits.”

Behind the scenes, he hustled to notify the family of victims as quickly as possible. “He made phone calls to very high-level people in this country to have them authorize the Florida Department of Law Enforcement to find these families,” Downs says. “He just kept saying over and over again, ‘I can’t imagine what it would be like to be a parent and not know if your child was alive.’ It was really hard.”

Challenges ahead

The COVID-19 pandemic has cast a pall over the cranes dotting the city’s downtown skyline and has created a new test of Dyer’s leadership.

As infections, deaths and fear rise across the country, a March report from the Brookings Institution predicts that Orlando could take a harder hit from the “COVID-19 recession” than other cities. The report lists Las Vegas as being the “most exposed” out of the nation’s 100 largest metro areas, with Orlando, the “theme park capital of the country,” following close behind. According to the report, 27.3% of jobs in Orlando are in industries “most at risk,” such as leisure and hospitality.

With 3½ years left in his term, other challenges remain for Dyer.

While programs have reduced the number of displaced veterans in recent years, homelessness continues to plague Orlando’s downtown. The benches in front of City Hall are sleeping quarters for some, and aggressive panhandlers solicit downtown workers on a daily basis. Downtown businesses complain about vagrants using bushes, sidewalks and doorways as toilets.

To try to combat the problem, the city has hired dozens of “downtown ambassadors” to escort workers and residents to their cars and connect panhandlers to social services that might help them. Since 2015, the mayor has supported a “housing first” strategy in Central Florida that utilizes private donations to pay for permanent housing for the chronically homeless. “There were days when the city was battling groups that were feeding the homeless in the park and stuff. (Dyer’s) really changed the city strategy from trying to force folks out of the view of people to try to get them into apartments,” says Mike Griffin, chair of the Central Florida Commission on Homelessness.

Tackling other problems, including a lack of affordable housing and an inadequate transportation infrastructure, will also require regional cooperation. Dyer would like to see SunRail extended to Orlando International Airport — but funding for the project and other transportation initiatives will depend on whether Orange County Mayor Jerry Demings can get voters to approve a one-cent sales tax increase.

The tax proposal was to be on the November ballot but has been postponed because of the coronavirus crisis. While Dyer’s relationships with previous county mayors including Jacobs were strained at times, he and Demings — who oversees a bigger budget, staff and region than Dyer — have known each other for decades and work well together. The former Orlando police chief calls Dyer “easygoing” and says he was “one of the first to embrace my transportation tax and housing initiatives, and I reciprocate by supporting his initiatives.”

Revitalizing Parramore and other blighted neighborhoods remains at the top of Dyer’s agenda.

There are pockets of progress. With Dyer’s help, the non-profit group LIFT Orlando and its Atlanta-based development partner, Columbia Residential, tore down the dilapidated and crime-ridden Washington Commons Apartments near Camping World Stadium and replaced it with Pendana at West Lakes, a 200-unit, mixed income apartment complex.

And in February, Dyer was all smiles at a ribbon-cutting ceremony for KRS Wealth Management, the first business to open in the new Amelia Court complex in Creative Village. “I like to say I am the happiest mayor in America — days like this are why I am happy,” he told the small crowd gathered on the sidewalk along Parramore Avenue.

But as redevelopment proceeds in Parramore, some longtime residents worry that single-family homes in the predominantly African-American community will be knocked down to make way for high-rise apartments with rents they can’t afford. Dyer has vowed “not to leave our neighbors behind” in Parramore, but political allies such as Morgan admit it will be a tough fix “without just a full-blown gentrification.”

In the meantime, Dyer’s had to fend off power plays by political adversaries.

In May 2019, state Sen. Dennis Baxley, an Ocala Republican, filed legislation to try to oust Dyer and Demings from the board of the Greater Orlando Aviation Authority, which manages the rapidly expanding Orlando International Airport. After the media got wind of it, Baxley withdrew the legislation. Through public records requests, the Orlando Sentinel traced the amendment back to Halsey Beshears, a Winter Park Republican who served in the Florida House of Representatives until 2019, when Gov. Ron DeSantis appointed him secretary of the Florida Department of Business and Professional Regulation.

During an interview, Dyer declined to comment on the attempted maneuver.

While Dyer’s name pops up periodically as a potential candidate for governor and other statewide office, some believe his 2005 indictment could be a stumbling block. Others say the only thing standing between Dyer and gubernatorial bid is bad timing. Their political calculus assumes DeSantis will be a shoo-in for re-election in 2022, not leaving a Democrat any realistic chance of winning until 2026, at which point Dyer will be 68 years old.

A couple of years ago, Dyer said the only other job he’d ever be interested in would be serving as president of the University of Central Florida — but he a took a pass when the job came open earlier this year.

For now, he says, “I’m still in a city that’s a teenager — we’re growing, and the future’s ahead of us. If you’re the mayor of Boston or Chicago or Philadelphia, you’re kind of set in your ways. You can kind of steer a little bit. But we can go anywhere … so it’s really fun to be the mayor at this point in the city’s life.”

Buddy Dyer, 61

• Hometown: Kissimmee
• Education/Experience: Bachelor’s degree in civil engineering from Brown University; law degree from the University of Florida. He worked for four years as an environmental engineer and served 10 years in the Florida Senate (1992-2002), including three years as Senate Democratic Leader before running for mayor.
• Family: Dyer divorced in 2017. He has two grown sons, Trey and Drew, and a labradoodle named Sammie, a frequent presence at City Hall.
• Spare Time: When he’s not working, Dyer likes to hike, hunt, fish, golf, read and watch sports. His wallet and several pairs of boots he wears are made from alligators he killed.
• Feedback: “I get more positive reinforcement about, guess what? My voice on the tram at the airport,” Dyer says. He also got e-mails from people around the world after he rescued a Jack Russell terrier from the jaws of a pit bull while he was jogging around his neighborhood in 2008. “People love their dogs.”
• Future Ambitions: Asked about running for higher office, Dyer replies that he “never says never” but for now is focused on leading Orlando.

 

Read more in Florida Trend's May 2020 issue.
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