Jeff Burlew | Tallahassee Democrat

Tori Lynn Schneider, Tallahassee Democrat

Scott Maddox, Tallahassee’s one-time “boy mayor” who wielded great power and influence at City Hall for decades, pleaded guilty in a federal public corruption investigation that began more than three years ago and appears anything but over.

Maddox, along with a former aide, Paige Carter-Smith, entered guilty pleas Tuesday in U.S. District Court in Tallahassee in a plea agreement with federal prosecutors. As part of the deal, most of the charges against them in a 48-count indictment were dropped in exchange for guilty pleas to three counts: honest services wire fraud, honest services mail fraud and conspiracy to defraud the United States.

The pair long denied any wrongdoing but last week asked for a hearing to change their not-guilty pleas. The move, which came after the government exchanged damning evidence against them, including secretly recorded conversations, likely means they plan to cooperate with the government to reduce their sentences.

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Scott Maddox, Paige Carter Smith enter courthouse for guilty plea

The case against Scott Maddox:

The plea deal marks a major turning point in an ongoing, four-year criminal investigation that the Tallahassee Democrat first broke two years ago and has continued to chronicle.

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U.S. Attorney Larry Keefe, during a news conference, would not confirm Maddox and Carter-Smith's cooperation in the corruption investigation, which began with the arrival of undercover FBI agents. But he said investigators are interested in exploring new leads.

"We hope that these defendants come forward and fully accept their responsibility and cooperate by providing truthful information about this case and about any potential criminal conduct beyond the scope of this particular case," Keefe said.

'Judge the defendants guilty'

The hour-long hearing before U.S. District Judge Robert Hinkle hit a high moment of suspense when it appeared the plea deal could unravel. Both Maddox and Carter-Smith equivocated when Hinkle asked whether they were guilty of acts described in their signed statements, prompting him to note they “danced around” his questions and wonder whether they really wanted to go to trial.

"You solicited payments in exchange for your vote," Hinkle said.

After huddling briefly with their lawyers, Maddox and Carter-Smith opted to plead guilty rather than pursue a trial, which had been set for Nov. 4. They gave straight-forward “yes, sir” and “no, sir” replies to a series of questions, including whether they understood the rights they were giving up and that they couldn’t change their guilty pleas once entered.

The Uber connection:

Maddox and Carter-Smith acknowledged their role in helping ride share giant Uber get a favorable ordinance in exchange for cash and accepting payments from a developer that turned out to be an FBI front company. They also admitted to keeping bogus books for their consulting firms and filing false documents for their real-estate deals, which carried over into Maddox’s tax returns.

“I accept the pleas and judge the defendants guilty,” Hinkle said.

The no-nonsense Hinkle also pointedly asked whether either of them had used alcohol or drugs in the 24 hours before entering their plea. Carter-Smith, former head of the Downtown Improvement Authority, conceded she drank two glasses of Jack Daniels the night before. Maddox said he put back some Woodford Reserve.

They face up to 20 years in federal prison on each of the fraud charges and up to five years on the income tax charge. They also face up to $750,000 in fines, forfeiture of any of their properties they obtained fraudulently and restitution payments to victims. Both will remain on pretrial release pending sentencing.

Hinkle set a sentencing date for Nov. 19 — a couple of weeks after a third defendant, local businessman John “J.T.” Burnette is set to go to trial. But it’s possible that could be pushed back depending on how long it takes Maddox and Carter-Smith to provide all the information prosecutors seek.

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Illustrations from the federal courthouse in Tallahassee | Gallery

A TANGLED WEB: A look at those under the microscope of federal investigators and their connections to the city, businesses and each other

Some City Hall observers were unhappy that prosecutors opted to drop so many counts, including the overarching racketeering conspiracy charge.

"Like many I’m sure, I am shocked and disappointed in the tremendous reduction in charges," said environmental activist Terry Ryan, who worried Maddox and Carter-Smith will get minimal prison time. "This will not reflect well on Tallahassee."

Erwin Jackson, who has long fed information to the FBI, said he was also disappointed so many counts were tossed out. He hopes Hinkle will take into consideration all of the allegations when he sentences the two.

"My feeling is he should get at least one year in prison for every year he's been a crooked politician, and that's about 20," said Jackson, who attended the hearing. "That seems fair. If it's less than that, what it's going to show the entire public is white collar corruption pays off really well."

'He wants to move on'

Maddox, 51, and Carter-Smith, 54, walked out of the federal courthouse separately with their attorneys, Stephen Dobson III and Stephen Webster. They appeared stoic, cracking an awkward smile or two, and declined to speak with reporters who crowded the courthouse steps. Dobson said Maddox was dealing with the recent death of his father and acting as sole caregiver to his stepmother, who is nearly blind.

“He wants to move on with his life, his family’s life and Tallahassee,” Dobson said. “And he hopes Tallahassee heals after all of this because much of his life has been devoted to Tallahassee and making it a better place to live.”

Maddox and Carter-Smith’s guilty pleas involve their dealings with ride share giant Uber, which sought favorable provisions in a city ordinance, and a development firm that turned out to be an FBI front company. Uber paid $40,000 to their consulting firm, Governance, over several months in 2015; Governance in turn paid Maddox $40,000. The front company sent four $10,000 checks to Governance from late 2016 to early 2017.

However, their misdeeds didn’t end there. In their signed statements, Maddox and Carter-Smith acknowledged the government could prove beyond a reasonable doubt other acts, including their acceptance of hundreds of thousands of dollars from companies including Waste Pro, the city and county’s trash vendor, and unnamed residential development and construction businesses.

Back story: Inside the Waste Pro deal that drew FBI scrutiny and spun off charges against Scott Maddox

John Camillo, president of Yellow Cab, which was on the other side of Uber in the ordinance debate, said Maddox and Carter-Smith’s actions hurt local businesses and drivers across the state.

“After Tallahassee amended its ordinance, many counties and cities in Florida followed suit, often citing what the commission in Tallahassee did,” he said in an email. “Local companies that had for years operated within the regulations were decimated and often eliminated. Drivers who had for decades made a living complying with regulations lost their livelihood.”

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Photos: FBI fake-out? Anatomy of an undercover operation

An Uber spokesman issued a statement saying, “We view ourselves as victims of extortion in this case, which is why we've cooperated fully with the FBI and the U.S. Attorney's Office throughout this process.”

O’Neal Jackson, a Tallahassee native and retired teacher and coach who attended the hearing, said he voted for Maddox early on but eventually stopped supporting him. He said he believed Maddox had ulterior motives for his votes ever since he led a charge to sell off city's electric utility years ago. But he didn’t know the full story.

“You can see the front and the back of the book, but you never know what’s in the book,” Jackson said. “And this was one of those cases where you never thought he was involved in all this stuff.”

The full extent of the evidence against Maddox may not be revealed until Burnette goes to trial, Keefe said. He added he appreciates the desire from regular citizens for closure in the corruption investigation.

"But the role of the Department of Justice in this is to be independent and to be completely blind to the political exigencies and to focus totally on the law and facts," Keefe said, "and to strike a balance between accelerating too rapidly and not doing our jobs effectively just to get it over with and have a sense of closure and just going on and on and on too long where you cause a greater harm by trying to seek a perfect outcome."

Contact Jeff Burlew at jburlew@tallahassee.com or follow @JeffBurlew on Twitter.

CHRONICLING THE CASE

The back story:

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Scott Maddox through the years | Photos

A Tangled Web: