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Meet the 23-Year-Old Student Who Raised $25 Million in Democratic Losses
After the Democratic candidates in Florida’s special elections burned through millions and millions of dollars on the way to double-digit losses this week, some Democrats are asking where that money deluge came from — and where it all went.
The answer to both questions is, in part, a 23-year-old law student and dungeon master — in Dungeons & Dragons — with a lucrative side gig.
In between classes and fantasy play, Jackson McMillan is also the chief executive of Key Lime Strategies, a small fund-raising firm in Florida that scored big when it landed as clients the two Democratic nominees in the Florida congressional elections, Josh Weil and Gay Valimont. Mr. McMillan said they had combined to raise $25 million.
“We’ve built a juggernaut,” he said in an interview.
Along the way, Mr. McMillan has piled up critics far beyond his years. Much of the focus is on his unusual fee structure, which one top party official excoriated in a cease-and-desist letter as “exorbitant.” His firm received a 25 percent cut of “true profits” — the proceeds after fund-raising expenses — for both special elections.
Mr. McMillan is unapologetic.
“A lot of the people who are critiquing me online are mad that it wasn’t them,” he said of raising so much money, which he said put a scare into Republicans and injected real money into long-neglected corners of a rightward-drifting state.
One secret ingredient to his firm’s success, Mr. McMillan explained, is Dungeons & Dragons.
“All the senior fund-raising strategists at my firm — myself, Ryan — we’re dungeon masters,” he said of his college friend and the firm’s chief operating officer, Ryan Eliason. “We run Dungeons & Dragons games. So we weave narratives and tales. It’s like our biggest hobby. We basically tell a really compelling story. And that’s what sets us apart from — that and a lot of technical analysis — is what sets us apart from some of our competitors.”
Others say the story his team spun up about Mr. Weil and Ms. Valimont made him a false-hope merchant who cashed in on the desperation of small Democratic donors wanting to fight the new Trump administration. These were lopsidedly Republican seats, which the G.O.P. won by more than 30 percentage points last fall and where Democrats faced near-impossible odds; the Republicans won by 14 percentage points on Tuesday.
Stefan Smith, a digital strategist who is head of digital engagement at the American Civil Liberties Union, called the 25-percent-of-profits fee structure “absurd” and said the races had diverted donor money from more urgent priorities under false pretenses of competitiveness.
“Democrats are experiencing the largest trust gap we’ve experienced in a generation, and we are not going to win that back by letting predators roam freely across the digital ecosystem,” Mr. Smith said, speaking in his personal capacity. “It is on all of us to hunt them to extinction.”
There is no single standard for fund-raising contracts, but more typically, consultants earn a retainer and either a percentage of what is spent creating and placing ads, or a much smaller percentage of what is raised overall.
So just how much did Mr. McMillan’s firm clear?
“I don’t think I’m totally comfortable sharing that,” he said, waving off talk that it had amounted to a multimillion-dollar payout and saying that all of the bills had yet to be settled.
“Don’t get me wrong,” he added. “My firm did well.”
Records show that by mid-March, the two campaigns had paid his firm $4.7 million, roughly 38 percent of their total spending.
Much of the money sent to Key Lime Strategies appears to have paid for fund-raising ads.
In the first 90 days of the year, Mr. Weil’s campaign was the single biggest political spender on Instagram and Facebook in the nation, spending $2.5 million. Ms. Valimont’s campaign was close behind, at $2.1 million.
Neither Mr. Weil nor Ms. Valimont returned calls for comment. Both sent written statements praising Mr. McMillan. Mr. Weil said the campaign’s payments to the company had covered polling and mailers, as well as email, text and social media messaging.
“The work he did on this campaign should cement Jackson McMillan as the gold standard for Dem fund-raising and political coordination in the state of Florida for years to come,” he said. Ms. Valimont said the funds helped to boost “voter registration efforts that would never have garnered any investment under normal circumstances.”
It’s an adage of online political fund-raising that you have to spend money to make money. (And raising big money brings more media attention, which in turn can bring in more money.) The question is if quite that much needed to be spent. Records show the advertising blitz overwhelmingly went to raising more money rather than persuading Florida voters.
Both Mr. Weil and Ms. Valimont, for instance, spent far more on ads in California than in Florida, records show.
All told, the Weil campaign spent far less on local television ads, $1.5 million, than out-of-state online fund-raising.
At one point in the race, Representative Alexandria Ocasio-Cortez, Democrat of New York, said she was being featured in fund-raising appeals without her permission. And lawyers for David Hogg, a Democratic National Committee vice chair, wrote a cease-and-desist letter asking Mr. McMillan to pull ads featuring Mr. Hogg because he would not “lend his name to fund-raising efforts that divert substantial portions of the proceeds from a campaign to cover exorbitant fees for fund-raising consultants.”
Mr. Hogg went even further in a post on X. “People like Jackson McMillan are the exact type of consultants who people say are the problem in our party,” he wrote.
In an interview, Mr. Hogg explained his decision to go after Mr. McMillan by name: “Nothing is going to change until we start calling these people out.”
Mr. McMillan said that the episode had been a “misunderstanding” and that the firm had pulled the ads and apologized. He noted that he and Mr. Hogg, 24, had risen in Florida politics at the same time and are of the same generation.
“We’re in the same space,” Mr. McMillan said. “And I would love to work together with Vice Chair Hogg more, and I think we have the same motives and goals, which is why I was very, very surprised to see his onslaught of attacks.”
Mr. McMillan is also the treasurer of the Florida Future Leaders PAC, a youth-organizing group formed last year. State records show the PAC paid Key Lime Strategies more than $534,000, roughly 65 percent of the group’s total expenses.
Mr. McMillan defended his firm’s pay structure, which is listed on its website, as cheaper and “more ethical” than some rivals, who sometimes take a smaller cut of the total raised, regardless of what the campaign is netting.
Mr. McMillan said he had actually stumbled into the digital fund-raising business.
He was once an aspiring paleontologist at the University of Florida, where he said he had enrolled early as a 15-year-old after skipping some grades. But a trip to Wyoming for a dinosaur-bone dig was interrupted by a car accident, and he recalled rethinking his career choice as he removed glass shards from his arm.
He met his business partner and current roommate, Mr. Eliason, in college. They formed the Magic the Gatoring club, where students gathered to play the fantasy card game Magic the Gathering, and a quick bond followed.
Mr. McMillan filed the paperwork for Key Lime Strategies in June 2022 and began doing political field programs for local races, including some for the Tampa City Council. “It was a lot of work for not a lot of payoff,” Mr. McMillan recalled of early fund-raising efforts.
But then came Ms. Valimont’s first long-shot bid for Congress, in 2024 against Matt Gaetz — a high-profile villain for many Democrats. Mr. McMillan, by then a full-time student, said it had been the “perfect contest” to experiment in.
Ms. Valimont raised $1.58 million. More than half — $812,824.15 — went to Key Lime Strategies.
She lost by 32 percentage points.
Then she ran in the special election, rehired Key Lime Strategies, raised millions more and lost again.
If fund-raising doesn’t work out, Mr. McMillian is already testing another business that he filed the paperwork for in January: using artificial intelligence to spot consumer complaints for potential lawsuits against “corporate bad actors.” “That is the kind of law that I am most familiar with,” he said, citing some courses and an internship last summer.
Either way, he is betting on himself — and his Gen Z colleagues.
“I will put money on a 20-something in politics every day over someone who’s been doing this for 40 years,” Mr. McMillan said. “Give them an energy drink, and they will outwork you 10 to one.”
Kitty Bennett contributed research.
News
Inside Trump’s Touring Exhibition of American Heroes
The museums, designed by conservative nonprofits and Trump appointees, tell the story of early America, from colonization to revolution. The one exhibition looking beyond the early years is the “Wall of American Heroes.” It is a list of 51 people, chosen to illustrate 250 years of American history.
A White House spokesman said they were “individuals who shaped this nation’s history, culture and spirit across generations.”
The people pictured on this national honor roll — and the people left out — help illustrate what this administration sees as the highlights of American history.
Amid the administration’s efforts to reshape the nation’s relationship with its past, Trump appointees heavily weighted the list toward a single era of American history — and a few specific kinds of hero.
The other exhibitions in the Freedom Trucks were crafted by a pair of conservative nonprofits, PragerU and Hillsdale College. But the “Wall of American Heroes” was created by Freedom 250, a nonprofit effort whose leaders were chosen by President Trump and that was created to lead the planning of celebrations of the nation’s 250th birthday, overshadowing a bipartisan congressional commission.
A spokeswoman for Freedom 250 said Mr. Trump was not directly involved in the selection of those featured.
But the list clearly tracks Mr. Trump’s own lifetime and the heroes of the conservative political movement.
The wall’s tilt toward heroes of the baby boomer generation, for instance, extends beyond Hollywood stars and musicians. Of the four religious leaders on the list, two — Archbishop Fulton Sheen and the Rev. Billy Graham — also appeared on TV regularly in the 1950s and 1960s. The only painter on the list is Norman Rockwell, known for his idealized depictions of American life in that period.
By contrast, there is only a handful of figures from the first decades of American independence.
“That’s a disservice, if your intention is to present the last 250 years,” said Sarah Weicksel, the executive director of the American Historical Association. “Because all of the people on this list are building on the work and struggles and progress that was made by the people in the 150 years prior.”
The “Wall of American Heroes” was inspired by a similar display in a traveling museum created by the State of Virginia. But Virginia’s display celebrates little-known historical figures.
Mr. Trump’s, by and large, celebrates people who are already well-known — and, often, people who were famous in their own time. For example, it praises P.T. Barnum, a circus impresario who used hoaxes and freak shows to draw crowds. The wall calls him an “icon of American sensationalism.”
The spokeswoman for Freedom 250 said that many of the names on the wall were drawn from a list of 250 people that Mr. Trump wants to include in a “Garden of American Heroes” in Washington.
The spokeswoman declined to say what criteria were used to narrow down the list.
The only president whose name appears on the wall — not on the list of heroes, but alongside his quotation — is Mr. Trump himself.
Explore the Wall of Heroes
Navigate the display by dragging from side to side.
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GOP Rep. Tom Kean, missing from Congress for months, set to return on June 30
Washington — Republican Rep. Tom Kean Jr. of New Jersey will return to Congress on June 30, his spokesperson said, after being away since March in an unexplained absence that has confounded Capitol Hill.
“Congressman Kean is eager to return to in person work on June 30 and resume a full schedule,” Kean’s spokesperson, Harrison Neely, told CBS News on Thursday. The New Jersey Globe first reported on his return date.
Kean’s whereabouts since he last voted on March 5 have not been disclosed. When he first made a statement about the absence in late April, the New Jersey Republican said he was addressing a “personal medical issue.”
Kean said earlier this month that he would return to Washington within a matter of weeks, at which point he would provide more details about his health.
“Right now I am focused on my recovery and under the advice of healthcare professionals, I will transition from virtual work to in person work within a matter of weeks. At that time I will be completely transparent as to the nature of my medical condition,” Kean said in a June 2 statement released by his campaign.
The statement came hours before polls closed in New Jersey’s GOP primary for his seat, in which he ran unopposed.
He has missed more than 130 votes during his absence.
House Speaker Mike Johnson told reporters earlier this month that he had recently spoken with Kean. Johnson said he was aware of the health issue, but would not disclose the details.
“What he’s dealing with is not very common and not a big thing,” Johnson said.
News
Video: Obama Presidential Center Opens in Chicago
new video loaded: Obama Presidential Center Opens in Chicago
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