Women, money, and Taylor Swift tickets: The life and death of a Florida Republican ‘kingmaker’

Warning: This story includes details about suicide and crimes of a sexual nature.

On Nov. 1, 2022, Taylor Swift revealed that she was going on tour for the first time since before the pandemic. Billboard would go on to describe it as “the most chaos-inducing tour announcement of the decade.” Far from Good Morning America’s studios where Swift sent her fans into a frenzy by announcing the Eras Tour that fall day, the news set into motion a series of events that would bring about the downfall of a man known in Florida as a Republican kingmaker.

The strange, salacious tale of the kingmaker’s demise and, ultimately, death began with a young Swiftie in Jacksonville, Florida.

Hoping to secure early access to tickets, which for many proved easier said than done, the young woman turned to an old family friend: Kent Stermon. Records show that Stermon quickly agreed to help and even dangled the prospect of backstage passes and the chance to meet Swift herself. Prosecutors would later note that the woman, whose identity has never been revealed, “was aware Stermon had offered other individuals assistance in obtaining access to special events such as concerts, and sporting events.”

But first, via what prosecutors described as “a bizarre and fraudulent scheme,” the woman had to prove she would fit in with the vibe they were curating for the VIP bash at Swift’s concert. Stermon instructed her to email a “backstage coordinator” he knew. The coordinator referred to Stermon as her “uncle” in emails, records show. The coordinator, with Stermon encouraging her along in phone calls and DMs, convinced her to send provocative photos, including one of her pouring beer over her bikini-clad body, and answer questions about her sexual history and boundaries, such as if she would go topless in a hot tub.

When she refused the coordinator’s request for photos of her naked breasts, they rated her a seven out of 10 in terms of the likelihood that she’d get the backstage passes. Via Facebook messenger, she told Stermon that this was her boundary; records show he replied, “Proud of you buddy.”

An investigation would later reveal that there was no backstage coordinator. The woman was actually corresponding with Stermon himself via a fake email he appears to have made for this purpose. Another email address he instructed her to send photos to belonged to a cop buddy of his. (The officer has not been accused of wrongdoing.)

On the afternoon of Nov. 18, Stermon summoned the young woman to his office to reimburse her for tickets she’d personally acquired at his behest. The likely awkwardness of meeting privately with a family friend, who at 50 was old enough to be her father, to receive $1,500 cash turned sinister and, she told police, frightening, soon after she arrived at the nondescript office where Stermon worked as an executive for a moving company that relocates military families.

During their meeting, Stermon bragged about his connections to powerful Republicans, claiming he was responsible for Florida Gov. Ron DeSantis (R) appearing onstage at a Luke Bryan concert a few weeks prior and at one point making a show of rejecting a call from Jacksonville’s then-Mayor Lenny Curry (R).

She later told police he was clearly “flashing his power at me” and said this was both intimidating and typical behavior. “He’s kind of a showboat. And he’s too charming. You know what I mean? Like tries too hard,” she said.

Stermon also peppered the woman with questions about her sexual history and shared explicit details about his own past.

Increasingly uncomfortable, she told police she began telling him what he wanted to hear.

“I was very frightened because he’s a bigger guy and I’m a small woman,” she said, adding, “In my head I was like I need to get out of here in the safest, least traumatic way possible without getting raped or hurt or killed. Because I didn’t know what this man was capable of.”

Then he started propositioning her. She told police she turned down $10,000 to give him a lap dance that he specified had be at least 20 minutes; the $5,000 he offered her for FaceTime sex was a non-starter as well. But before she could leave, Stermon demanded she give him something in exchange for the $1,500—and it had to be more than 30 seconds. Desperate to escape, she agreed to let him see her naked breasts; through tears, she told officers that when it was over, he pointed to his crotch to show her how excited he was.

Afterward, Stermon led her out the back door—she’d gone in the front, so this was arguably odd—where she said he insisted on physical contact, saying, “You’re that uncomfortable, you can’t even give me a hug?”

She could’ve tried to forget. Instead, she told her family. Later she and her father confronted him at a Panera Bread. Her father told police that Stermon had readily agreed to meet, perhaps so accustomed to getting his way and never having anyone push back that he didn’t expect the meeting would be anything but a casual conversation between old friends. Instead, it was a blow-up in which the father told Stermon that he’d “[expletive] with the wrong family” and purportedly said he’d “bury” him. The woman told investigators that she said to Stermon, “You will never do this to another woman ever again.” She said the man who’d bragged about rejecting the mayor’s call and seemed to have an endless supply of powerful friends reacted to the confrontation like a 12-year-old getting scolded, “scurried out,” and peeled out of the parking lot so fast that an observer wrote down his license plate.

Subsequently, she and her father reported Stermon to the police, who launched an investigation.

Stermon was at the height of his power. He had it all: A $2 million house in an exclusive community, a cushy job, plenty of money, and friends in high places.

Learning he was being investigated appears to have sent Stermon into a rapid downward spiral, however. Days later, he had a stroke and was temporarily hospitalized. Records from the investigation show that he began searching for information on the penalty for soliciting prostitution, how to delete various online accounts, for a criminal defense lawyer, and how to kill yourself.

Then, on Dec. 8, his body was discovered in his vehicle at a local post office. He’d fatally shot himself. In a suicide note addressed to “sis” and a redacted name, he wrote, “I love you both too much to put you through this. You’re better off w/o me. Go find your own version of [redacted] and be happy!”

Stermon’s powerful friends were stunned. He was an influential figure in Florida—a longtime political reporter there described him as the “man behind” DeSantis. People say Stermon had a commanding presence and clearly enjoyed flaunting his wealth and connections, just as he did with the young woman in his office the day that brought everything crashing down. He was known as a guy whose ring people had to metaphorically kiss to get access to DeSantis or simply run for office, part of the political machine that controls much of Florida, a machine that includes donors, politicians, and consultants. Those who went up against Stermon and his allies say that they could and would make or break people at will. Many cogs in this machine, like Stermon, have voracious appetites for money, power, and the trappings of success.

These same desires that made Kent Stermon also brought about his downfall.

After his death, DeSantis’ office released a statement saying, “The Governor and First Lady were shocked and saddened to hear of Kent’s passing, and their prayers (and our entire office’s prayers) are with his family during this difficult time.” The Board of Governors, the influential body that has authority over the state higher education system, which DeSantis appointed Stermon to in 2019, expressed its “heartfelt condolences” and touted Stermon’s history of being “a champion of higher education and student success in Florida.” Others who’d known him made similar statements.

The outpouring of support fell to a hush when news broke that Stermon was under investigation for sexual misconduct at the time of his death.

The dead can’t be prosecuted; nevertheless, the State Attorney’s Office (SAO) continued investigating whether there were other victims, perpetrators, or if this was part of a “broader fraudulent scheme.” Nine months later, the SAO said it had determined Stermon could’ve been tried for multiple crimes: false imprisonment, solicitation of prostitution, theft by false pretenses, and unlawful use of a two-way device.

The SAO concluded that there were no other victims nor anyone else involved in Stermon’s scheme.

“Because the investigative objectives have been met, and in light of Stermon’s death, we will be taking no further action in this matter,” the SAO’s disposition memo states.

With that, the case was closed.

Questions linger to this day. Although the investigation found otherwise, many are convinced there were other victims. And if so, they wonder what, if anything, did his powerful friends, including in the police, know about it? Had other incidents been covered up? The young woman said Stermon claimed that he paid an assistant $10,000 for one lap dance per year so she could make ends meet. The sheer brazenness of the scheme to prey on this young woman, along with the facts that he’d known her since childhood and was friends with her parents, convinced many that this was not a first time offense.

Some whisper that Stermon’s allies in government and elsewhere would rather never see the whole truth about the fallen kingmaker come to light.

This story is based on more than 7,000 pages of records the Daily Dot received via a public records request from the DeSantis administration, hundreds of campaign finance and business records, dozens of news reports, prosecutor’s investigative files, and interviews with experts and members of Florida’s political class.

The records request sought all correspondence to and from the governor’s office in 2022 that included Stermon’s name or that of the companies he owned or worked for. Notably, none of those records, which took many months and a threat of litigation to obtain, include any emails from the governor’s official email address. DeSantis has been repeatedly criticized for arbitrarily denying or delaying public records requests. His administration has been sued for delaying releasing records and for asserting that executive privilege precludes him from providing his communications.

The rise of a kingmaker

Stermon’s first known tie to the Florida political establishment was formed in college when he roomed with Florida state Rep. Travis Cummings (R), with whom he remained friends until his death. After college, he worked for a couple of large corporations before landing a job at Jacksonville-based Total Military Management (now known as TMM), according to an archive of his profile on the company’s website.

In the decade-plus he worked for TMM, Stermon rose through the ranks to become president of the company, a role he held until his death. As his career advanced, so did his involvement in Florida politics. A longtime Jacksonville resident who formerly served in public office recently told the Daily Dot that Stermon “kind of came from nowhere.” They requested anonymity for fear of reprisal from state powerbrokers.

Stermon showered money on Republicans. Campaign finance records show that from 2009 on, he and his family donated at least a cumulative $350,000 to candidates for state, federal, and local office. The vast majority of his federal donations went to representatives who served on committees with authority over Department of Defense (DoD) spending, which makes sense given that he was an executive with a company that gets significant DoD contracts. TMM says it coordinates the relocation of 60,000 members of the military and their families annually, purportedly more than any other DoD contractor in the business.

Other recipients of Stermon’s largess include DeSantis, former Jacksonville Sheriff Mike Williams (R), Jacksonville Sheriff T.K. Waters (R), state Rep. Jessica Baker (R), and many other Florida Republicans.

Stroking checks has a way of opening doors—for Stermon literally and figuratively. In 2013, Jacksonville Sheriff John Rutherford (R), who is now a member of Congress, issued Stermon a badge to access Jacksonville Sheriff’s Office (JSO) facilities, according to Jacksonville Today, which he would retain until his death. The outlet reports that at the time of Stermon’s death roughly 400 non-JSO employees had badges, but the vast majority were contractors, vendors, or interns. Stermon was among a select group of nine people who were granted access as members of the “sheriff’s circle.” Stermon’s access was revoked around the time police started investigating him. In the wake of Stermon’s death, Sheriff Waters said he’d discontinued the sheriff’s circle entirely.

Even among the nine, Stermon’s access was exceptional.

Six months before his death, Folio Weekly broke news that he could come and go freely at JSO facilities. (Disclosure: I was the editor of Folio Weekly from 2016 to 2018.) In response to media requests at the time, JSO said there were no records of Stermon using his badge. Mere weeks after his death, JSO released records showing that Stermon used his badge to enter its facilities on nearly 200 separate dates from 2017 to 2022, often multiple times in a single day, for a grand total of more than 700 swipes. The other eight members of the sheriff’s circle, on the other hand, rarely if ever used their badges. The sheriff’s office reportedly blamed a “software issue” for the records’ temporary disappearing act. Some say they still don’t believe this explanation.

Former Sheriff Mike Williams, who today heads the Jacksonville division of the Florida Department of Law Enforcement (FDLE), did not respond to inquiries.

JSO insiders, speaking on condition of anonymity, told the Daily Dot that Stermon would go into areas that contained sensitive information about ongoing investigations, including sex crimes, which some find particularly disconcerting in light of what the young woman accused him of doing to her. If anyone questioned his access, they said, their concerns were brushed off at best. Stermon was known to be vindictive, insiders say.

It was common knowledge that crossing Stermon could hurt an officer’s career and that he had the sheriff’s ear, particularly when Williams was in office. Florida Politics reports that Williams’ “friend and confidant” Stermon served as the finance director for his successful 2015 campaign that raised nearly $550,000. The following year, JSO named him “citizen of the year.” Records the Daily Dot obtained show that on two occasions, as recently as the August before his death and once when Williams was sheriff, he listed a Mike Williams as his emergency contact when he went on ride-alongs with officers on duty. On one of those forms, Williams’ address is shielded under the law preventing the release of information about officers’ residences. The other lists JSO headquarters as Williams’ address.

Mirya R. Holman, a professor of public policy at the University of Houston, has extensively studied county sheriffs and the power they wield. She’s co-authoring an upcoming book on the subject with Emily M. Farris, a professor at Texas Christian University. Holman recently told the Daily Dot that it’s not particularly unusual for sheriffs to grant special privileges to civilians.

“Most of the time that is used as a fundraising component, which seems to be a piece of this,” Holman said. “Sheriff’s posses are often people who donate money to the sheriffs.”

Sheriffs have gotten in trouble for selling access, she added, but it’s rare. Their powers are vast and some states allow them to deputize civilians. During the 2020 civil rights protests, the sheriff a county over from Jacksonville made national news by threatening to deputize gun owners in case protesters got unruly.

Of reports that Stermon carried on like he was actually a police officer, Holman said, “This sort of cosplaying being a cop, it’s weird, but I can’t say that it’s that unusual.”

JSO insiders and others involved in Florida politics who knew Stermon told the Daily Dot that Stermon wore police insignias during ride-alongs and on other occasions and was even known to jump into the fray when officers were using physical force on a suspect. Perhaps he liked people to think he had the authority of a police officer.

The Daily Dot requested the names of all officers Stermon joined on patrol, as well as the dates of each ride-along. JSO provided three, two in 2020 and one in 2022. According to the forms, all three were with the same officer in the K9 unit.

Impersonating a police officer is a felony in Florida. People can also be charged with a crime for accessing state or federal law enforcement databases without authorization or simply giving out confidential information about investigations. (It’s not clear whether Stermon accessed these databases.) Earlier this year, a JSO officer was charged with accessing law enforcement databases and passing the information along to “criminals.” News4Jax reports that six JSO employees have been charged with providing confidential information to unauthorized people since 2011.

A year before Stermon got access to JSO facilities, he made the first of many donations to a political newcomer who’d just launched his first campaign for public office: Ron DeSantis. Over time, Stermon developed a reputation for being a trusted member of DeSantis’ inner circle, a particularly remarkable fact given how notoriously cloistered DeSantis is. Stermon reportedly served as the Northeast Florida chair for his first governor’s race, chaired a committee during DeSantis’ transition, and was known to be the man you had to see to get to DeSantis. A 2019 article in Florida Trend described him as one of DeSantis’ “closest friends” and “a prominent figure in Northeast Florida politics.” He was listed only behind Florida First Lady Casey DeSantis and the consultant widely credited with saving DeSantis’ first campaign, with whom the governor later had a falling out.

“You had to go through Kent to get to DeSantis …  he was holding the purse strings,” a Jacksonville political insider recently said.

DeSantis’ office did not respond to inquiries about Stermon. A source familiar with the matter said that Stermon was not actually a gatekeeper to the governor, but that he liked to give the impression that he was.

DeSantis’ relationship with Stermon did cause a couple minor scandals over the years. In 2018, a South Florida attorney filed an ethics complaint over Stermon and a colleague at TMM renting DeSantis a condominium they co-owned after his congressional district lines were redrawn. The complaint alleged they charged a below-market rate, which would violate rules prohibiting representatives receiving gifts, was rendered moot when DeSantis resigned to run for governor. The Naples Daily News noted that the rent charged was consistent with market estimates for similar properties.

In 2019, First Lady Casey DeSantis took some heat for flying in a donor’s private jet to attend a fundraiser at TMM for the Republican Party of Florida. Stermon brushed it off, telling Politico that he enjoyed seeing his “good friend” for lunch.

“I held a successful fundraiser for the Republican party of Florida. I appreciate the First Lady’s continued friendship and support of the party,” he reportedly said.

Along the way, Stermon met and befriended political consultant Tim Baker. Baker worked on DeSantis’ first congressional campaign. Records show that Baker’s company, Data Targeting, was also paid $225,000 for “research/consulting” in DeSantis’ first gubernatorial campaign.

Baker may have been Stermon’s most influential friend of all. Via email, Baker characterized their relationship as more business than personal, telling the Daily Dot that the two “were friendly over the years in the context of support for various political candidates and causes such as support for our law enforcement community.”

Baker has become one of the go-to conservative consultants in Florida, working on successful campaigns for local, state, and federal representatives, many of whom reportedly go on to do his bidding. Baker denied exerting such influence over his clients, saying that he has simply lobbied them on occasion at the behest of a client, which he has always disclosed in accordance with the law. “I don’t know what ‘do your bidding’ means,” he said.

His successes are many, his defeats few.

Two key exceptions came the same month last year. That May, Democrat Donna Deegan bested Baker’s candidate, Republican Daniel Davis, in the Jacksonville mayoral race. Weeks prior his wife, now a member of the state legislature, lost her bid to become Speaker of the House. The race was viewed as a proxy war between DeSantis, who has purportedly come to detest Baker for reasons unknown (some suggest it’s because the governor has refused to take orders from Baker), and former President Donald Trump. DeSantis backed the victor because, according to Florida Politics, he viewed Baker as a “stalking horse” for Trump “with whom Tim Baker, Jessica’s political consultant husband, is identified as being in close proximity.”

Those May disappointments aside, he’s been wildly successful in Florida politics, climbing the ladder at the same time Stermon was making his mark.

Today Baker is one of the most quietly powerful people in the state.

A political insider told the Daily Dot they believe Baker has hitched his wagon to Trump in the hopes of taking his machine national.

“The thing about the governor is in a year Tim is going to be the power still,” said Christina Meredith, a Republican who ran against Baker’s wife for Florida House.

The height of power

Longtime political reporter Peter Schorsch, the publisher of Florida Politics, described Stermon as DeSantis’ “bestie” in a 2020 list of influential Floridians. DeSantis appointed Stermon to the Board of Governors, which has authority over the state’s university system and has been particularly visible amid the governor’s ongoing war on education.

Records the Daily Dot obtained from DeSantis’ office give further clues as to the nature of their relationship.

On one occasion, Stermon acted as the go-between to get the governor to do a video for Jacksonville University. He wrote that his contact at the university “has always been very helpful and supportive of the Governor. He is often times a guest on local tv and always very supportive of the boss. If we could accommodate this I would appreciate it.” Within minutes, the governor had agreed to do the video, records show.

On another occasion, a top DeSantis’ aide informed FDLE, which provides security for the governor, that Stermon would join him in the motorcade during a visit to Jacksonville. DeSantis isn’t known for palling around with just anyone—even former Republican colleagues in Congress have said he “had no friends.”

Another document from 2022 placed Stermon at the top of the list of people from Northeast Florida to invite to an event, above the mayor, the sheriff, and other prominent politicians.

In one exchange that year, Stermon forwarded the curriculum vitae of a young man he’d apparently met with who wanted to work for the governor to DeSantis’ office, commenting simply “very impressive young man.” Within minutes, a DeSantis’ aide replied, “Wow! For sure. Will also share with Chris Spencer for OPB consideration. Thanks for sharing!” The aide was apparently referring to the Office of Policy and Budget.

A seemingly innocuous communication between Stermon and the governor’s office that year has become significantly more intriguing in light of subsequent political appointments.

Records show that on Feb. 1, 2022, Stermon emailed one of DeSantis’ senior advisers a link to a story about Freddie Figgers, who owns a telecommunications company. The email, which had the subject line “hey buddy,” said, “Do me a favor and read this and call me.”

According to campaign finance records, one day prior, Figgers donated $25,000 to the political committee supporting Sheriff T.K. Waters, whose campaign Stermon supported. The previous November, Figgers had also donated $25,000 to a political action committee (PAC) that supported DeSantis.

Several sources said Stermon actually tapped Waters to run for sheriff after others either declined or said they wouldn’t let him use JSO as his playground if they were elected. Waters denies it.

“Kent Stermon did not have any involvement in Sheriff Waters’ decision to run for Sheriff. After Sheriff Waters won the special election but prior to taking the seat, Mr. Stermon was notified that he would not have any privileged access to the sheriff and the building. This was done prior to the investigation and before Sheriff Waters officially took office as Sheriff,” he said in a statement.

In the two years since Stermon emailed DeSantis’ office about him, Figgers has secured plush appointments, a no-bid contract, and an earmarked item in the state budget. In March 2023, DeSantis appointed him vice chairman of Enterprise Florida, which promotes economic development in the state. The following month, Figgers accompanied DeSantis on a trip to Tokyo to meet with the Japan Business Federation. DeSantis also named him to the State Board of Administration’s Investment Advisory Council.

Last summer, DeSantis appointed Figgers to the Florida Commission on Ethics. Within weeks, the Central Florida Tourism District that replaced Disney’s special district amid DeSantis’ war with the theme park gave Figgers company a no-bid million-dollar deal, according to emails obtained by Florida Bulldog. After word got out about the contract, Figgers’ canceled it. All insisted that there was no wrongdoing.

A nonprofit Figgers runs also received a $500,000 earmark in the 2024 Florida budget to distribute tablets to at-risk youths and seniors, first reported by journalist Jason Garcia. Figgers Communications makes tablets. The funding request does not explicitly state where the nonprofit is to acquire the tablets. State records show that seven different legislators submitted requests for the appropriation.

Figgers did not respond to questions.

Currency united

In interviews last summer and in recent weeks, multiple political insiders in Florida described Stermon as a money man. As campaigns become ever more expensive, even on the local level, candidates need massive amounts of cash to be competitive. Stermon was a guy who could get the funds flowing. All you had to do, sources say, is obey the wealthy benefactors.

Christina Meredith vividly recalls meeting with Stermon at the suggestion of her pastor from Eleven22, a Jacksonville megachurch, after she decided to run for a seat in the Florida legislature.

She said her pastor told her, “You need to meet Kent. He is the kingmaker.” She thought this was a strange description for a man of the cloth to use, but agreed to sit down with the so-called kingmaker.

The bizarre meeting in Stermon’s office, the same place he made the young Swiftie show him her breasts, left a distinctly unpleasant impression of the man.

Meredith was seven months pregnant at the time of the meeting, which her husband and a female political consultant also attended. None of that stopped Stermon from making crude, sexual remarks throughout. He talked about how he couldn’t be trusted around women and asked her how she would handle the sexually charged atmosphere in the Florida legislature if she won the seat.

“It was so inappropriate and so uncomfortable,” she said.

She said he also promised to hook her up with major donors. That never happened. Meredith said that any support Stermon may have gotten her evaporated when political consultant Tim Baker’s wife, state Rep. Jessica Baker (R), decided to run for the same seat. Meredith said Kent warned her not to run against Baker.

“Kent Stermon was Jessica’s No. 1 supporter,” she said.

The Bakers ran one of their typically vicious campaigns against Meredith. They blanketed Jacksonville with ads and mailers calling Meredith, a Republican and longtime resident of Northeast Florida, a “California liberal” because she lived there as an adult and won the Miss California pageant. She said they even questioned her story of surviving years of child rape, which has been extensively documented, including in her memoir, CinderGirl: My Journey Out of the Ashes to a Life of Hope.

Both Bakers deny questioning Meredith’s history of childhood trauma. In an emailed statement, a staffer for Rep. Baker characterized Meredith’s past as a “sad tragedy” and denied that Baker had any role in downplaying it. “Nowhere in that story, or elsewhere, is there any comment from Jessica about that topic,” the staffer said, referencing a story in Florida’s Voice, an outlet Columbia Journalism Review has characterized as “a small, hyper-partisan right-wing news site.” Florida’s Voice owner Brendon Leslie declined to comment.

The staffer further noted that Stermon donated $1,000 of the roughly $450,000 Baker raised.

Weeks after she lost the election, Meredith says her husband was fired from the megachurch. She believes that Stermon, who was a major benefactor to Eleven22, may have had a hand in it. Eleven22 did not respond to an emailed inquiry.

In a move she views as tantamount to stealing her story, one of first bills state Baker filed was a law Meredith had been advocating for years—based on her own life experience as a survivor of child sexual assault—that allows people who rape children under the age of 12 to get the death penalty. DeSantis signed the bill into law last May. Meredith noted bitterly that it’s become one of his talking points.

“Here’s how I feel about the governor: Betrayed,” she said.

She said that DeSantis didn’t get publicly involved in the race, but she got the impression that he supported Baker. “He did … allow Jessica to make it seem like he had endorsed her on all her mailers and commercials and text messages so I just assumed they were all in bed together,” Meredith said.

Meredith was one of many people who recalled that Tim Baker and Stermon were friends. Both belonged to the world of money and influence that courses through Florida politics.

“Nobody can stop them,” she said of the Bakers.

Tim Baker downplayed his influence. “I get that people have loved to make me a boogy [sic] man for all things they don’t like but the reality is far more boring,” he told the Daily Dot via email. “It’s far easier to attack some consultant as bad than it is to say ‘[expletive] the mayor or councilman’ because they didn’t do what you wanted or your project didn’t get funded or you didn’t get a client but the reality is I’ve never been the one standing in the way.”

He characterized the people who lob accusations at him as “disaffected losers.”

Emily Nunez also went up against the machine and lost. Nunez, a Republican, said she was similarly warned it would be “ugly” if she got in the race. “They just kept hammering me over and over again … it’s like copy paste, ‘liberal Democrat, Emily wasn’t there when DeSantis needed her most,’” she recalled in a recent conversation.

Multiple sources told the Daily Dot that Baker’s venom doesn’t only extend to his candidates’ opponents. If any of his former candidates step out of line, it’s common knowledge that Baker will not hesitate to threaten them. People say he can be charming—until he’s not.

Republican political veteran Robin Lumb told the Daily Dot, “Baker is intelligent and superficially charming but he’s the most ruthless campaign consultant I’ve ever encountered.”

Multiple people familiar with Baker’s work said that he gets clients to share their darkest secrets, anything that the opponent might use against them in the campaign, “and then they have you.”

Baker denies threatening any of his clients. “I think if you actually asked the good people I’ve helped in their campaigns they would tell you the exact opposite of your sources’ assertions: I don’t ask my friends to do anything (and they often kindly complain that I am hard to get a hold of),” he said.

Nunez, Meredith, and multiple others described a shadowy web of power in Florida that extends from moneyed interests, like Stermon and his wealthy cronies, to consultants like Baker and his colleagues who shuffle dark money from committees to PACs to 501(c)(4) nonprofits, occasionally 501(c)(3) nonprofits, and back again in a seemingly endless shell game of transactions that obfuscates the original source of the funds. The representatives who tap into this web, several sources said, are often little more than automatons doing the consultants’ and donors’ bidding.

In January, the Florida Trident published a story about “Jacksonville’s culture of corruption.” Several current and former members of Jacksonville City Council described a corrupt political machine that poured money from special interests into PACs and campaigns run by Baker.

Dark money expert Maurice (pronounced “Morris”) T. Cunningham said that such funds have become pervasive throughout the nation since the Citizens United decision paved the way for unlimited giving. He said that the wealthy benefactors whose dark money is increasingly infiltrating races all the way down to the local level like to hide that they’re behind the donations in part because their legislative priorities are so different from average Americans.

Cunningham said “alarm bells” should ring every time funds shift around so much it’s impossible to figure out where they came from. “By any commonly understood definition, it’s corruption. But it’s legal,” he said.

“How can you say we’re a democracy when we make public policy in this fashion?” Cunningham added.

Conservative political insider Lumb is dismayed by what he sees happening in Florida.

“There was a time when the state party could be counted on to protect the integrity of the Republican brand,” he said. “That time has passed. Now it’s the ‘dark money’ PACs and power brokers who are pulling the strings.”

Multiple people said that Baker also takes money from corporations in exchange for access to his clients. Baker denies it, saying that he simply works as a lobbyist at times and always fully discloses it. After an effort to sell JEA, Jacksonville’s public utility, went up in smoke amid a scandal that recently saw its former CEO convicted of federal crimes, reports emerged that Baker had been retained by Florida Power & Light, which wanted to buy the utility, as a consultant. At the same time, he was advising JEA on the sale, which sources described as effectively playing both sides. (Disclosure: My spouse works for JEA.)

“It’s clear that they push policies and legislation that benefit his clients and don’t benefit the people,” Florida state Rep. Angie Nixon (D) said of Baker, whom she knows by reputation. “…They want people to be beholden to corporations.”

Some say that Stermon had an arrangement where he’d provide consulting for companies and people—for a price—and in exchange, get them in the room with a politician willing to do what they wanted.

A kingmaker falls

Stermon’s death stunned Florida’s political aristocracy. News that he was under investigation at the time was an even bigger bombshell. Or was it?

Several people said that they weren’t particularly surprised to learn that a woman had accused him of a crime. Those who knew him even casually describe him as something of a braggart who assumed an at-times uncomfortable level of familiarity, including by commenting on the appearance of women he found attractive with mere acquaintances. Several people who talked to the Daily Dot for this story believe there are other victims who chose not to come forward. It does seem rather pointless to accuse a dead man, after all, and most survivors of sex crimes don’t report it to police. It’s also arguable that any potential victims may have been intimidated by the wealthy man with powerful friends who was so embedded with police that he had his own parking spot.

“He liked to throw money around,” recalled political consultant Raymond Johnson of Stermon. Johnson is one of a small but growing number of Floridians who have publicly gone against the Bakers and their associates. “In this business, you don’t just get in unless you’re incredibly wealthy, unless you’re a Kent Stermon,” he said.

“These guys are so narcissistic that they are literally out of their mind,” Johnson opined of the machine that controls much of Florida from behind the scenes.

Among the records obtained by the Daily Dot, one email stands out. In the spring of 2022, a woman who worked for the governor emailed another woman in the office a four word message: “Kent Stermon got me.” There were no responses to the email included in the records.

The Daily Dot is not identifying the woman, who did not respond to multiple inquiries, because the context of the email is unknown. Her social media accounts and LinkedIn page show that the woman, who is attractive and young, had worked for DeSantis’ office for a few months at the time.

Multiple sources wondered if Stermon’s reason for buddying up with cops wasn’t simply because he enjoyed feeling that sense of power. They believe it may have been a preemptive move by a man who played by his own, rather than society’s, rules. No current or former officer has been implicated in crimes involving Stermon, including his scheme with the young woman over the Taylor Swift tickets, though they did interview one during the investigation.

One of the two email addresses Stermon gave her to send photos belonged to a police officer, prosecutors say. The files released after the investigation concluded contain video of him being interviewed on two separate occasions after Stermon’s death.

The officer admitted he received the images, which he described as “innocent,” “standard modeling pictures” and claimed he simply assumed Stermon was trying to hook him up with her because he was going through a divorce. He said that his friend Stermon was known to hook other men up with women.

He insisted he had no knowledge of Stermon’s elaborate ruse, though he did say Stermon told him that he was potentially going to give the woman Taylor Swift tickets but hadn’t made his mind up yet. Investigators cleared the officer of any wrongdoing.

If the young Swiftie had kept his money and her silence, today Stermon may have been greasing wheels and swinging his power around Florida. Instead, he’s dead and gone—but the machine grinds on.

Correction: In one instance, this article incorrectly stated Jacksonville Sheriff T.K. Waters’ (R) name.

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