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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
Tracking U.S. Military Killings in Boat Attacks
Since Sept. 2, the U.S. military has been attacking boats in the Caribbean Sea and eastern Pacific Ocean that the Trump administration says are smuggling drugs, killing dozens of people. A broad range of legal specialists on the use of lethal force have said that the strikes are illegal extrajudicial killings because the military is not permitted to deliberately target civilians — even suspected criminals — who do not pose an imminent threat of violence.
This is a drastic departure from past practice. The Coast Guard, with assistance from the Navy, has typically treated maritime drug smuggling in the Caribbean as a law enforcement problem, interdicting boats and arresting people for prosecution if suspicions of illicit cargo turn out to be correct.
The White House has said the killings are lawful. It cited a notice to Congress in which the administration said President Trump “determined” that the United States is in a formal armed conflict with drug cartels and that crews of drug-running boats are “combatants.” It has not supplied a legal theory to bridge the conceptual gulf between drug trafficking and an armed attack.
The New York Times is tracking the boat strikes as details become available. The strike locations and casualty figures are drawn from postings by Mr. Trump or Defense Secretary Pete Hegseth, and have not been independently confirmed by The Times.
Known U.S. strikes in the Caribbean and Eastern Pacific since Sept. 2
- Strikes
- 14
- Killed
- 61
- Survivors
- 3
Each entry is accompanied by an image taken from overhead of the boat or boats in the water shortly before the strike.
This was the sixth strike in the Pacific in eight days.
This was one of three strikes on four boats in one day in the eastern Pacific Ocean. Mr. Hegseth said that Mexican search and rescue authorities had “accepted the case and assumed responsibility for coordinating the rescue,” but he did not release further details.
This was the second strike in the same day in eastern Pacific Ocean.
This was the third strike in the same day in the eastern Pacific Ocean.
This attack, in the Caribbean Sea, was the first at night, Mr. Hegseth said.
This was the second strike in the eastern Pacific Ocean.
This was the first strike in the eastern Pacific Ocean, an expansion of the strike campaign.
Mr. Hegseth described those on the boat as affiliated with Ejército de Liberación Nacional, a Colombian guerrilla group. The strike took place in the Caribbean Sea.
This strike was on a semisubmersible in the Caribbean Sea. Two men from the boat were rescued by the U.S. military and repatriated within days to Colombia and Ecuador.
This strike took place “just off the Coast of Venezuela,” Mr. Trump said.
Colombia’s president said this boat was carrying Colombian citizens.
Officials from the Dominican Republic said they recovered cocaine from the wreckage after this strike.
Colombia’s president said the strike occurred near his country and killed an innocent fisherman.
The first strike on a boat alleged to be carrying drugs was near Trinidad in the Caribbean Sea. The boat appeared to have turned around before being struck.
News
WATCH: Massey family speaks at vigil after Illinois sheriff’s deputy convicted over killing of Sonya Massey
PEORIA, Ill. (AP) — A jury on Wednesday convicted an Illinois sheriff’s deputy of second-degree murder, a lesser charge, in the shooting death of Sonya Massey, a Black woman who called 911 to report a suspected prowler.
Watch Massey’s family and supporters speak after the verdict in the video player above.
Sean Grayson could be sentenced to up to 20 years in prison or even probation. The jury did not convict him of first-degree murder, a crime that carries a sentence of 45 years to life.
Massey’s supporters were angered by the result. Her father, James Wilburn, called it a “miscarriage of justice.”
WATCH: Activists demand reform and justice after deputy shoots and kills Sonya Massey in her home
“She called for help and she was murdered in her own home. … Second-degree murder — that is not right. That is not justice for anybody’s family,” Teresa Haley, a civil rights activist in Springfield, Illinois, told reporters outside the courthouse.
Grayson and another deputy arrived at Massey’s home in Springfield early on July 6, 2024, after she reported a prowler. He shot the 36-year-old woman after confronting her about how she was handling a pot of hot water on the stove.
Grayson and his attorneys argued that he fired his gun in fear that Massey would scald him with hot water.
Massey’s killing raised new questions about U.S. law enforcement shootings of Black people in their homes, and prompted a change in Illinois law requiring fuller transparency on the background of candidates for law enforcement jobs.
Grayson, 31, was charged with first-degree murder, but the jury was given the option of considering second-degree murder, which can apply when a defendant faces a “serious provocation” or believes their action is justified even if that belief is unreasonable. He will be sentenced on Jan. 29.
State’s Attorney John Milhiser declined to comment as he left the courtroom. He was repeatedly praised by Massey’s supporters for pursuing a trial that was moved 75 miles (120.7 kilometers) north to the Peoria County courthouse because of intense publicity in Springfield.
Defense attorney Daniel Fultz declined comment after the verdict.
“While we believe Grayson’s actions deserved a first-degree conviction, today’s verdict is still a measure of justice for Sonya Massey,” the family’s attorneys, Ben Crump and Antonio Romanucci, said after the seven-day trial.
FILE PHOTO: The family of Sonya Massey, a 36-year-old Black woman shot and killed by an Illinois sheriff’s deputy during a call for help at her home, holds a press conference and rally at New Mount Pilgrim Missionary Baptist Church in Chicago, Illinois, July 30, 2024. Photo by Vincent Alban/Reuters
Body camera video recorded by another Sangamon County sheriff’s deputy at the scene, Dawson Farley, was a key part of the prosecution’s case. It showed Massey, who struggled with mental health issues, telling the officers, “Don’t hurt me,” and repeating, “Please God.”
When the deputies entered the house, Grayson saw the pot on the stove and ordered Massey to move it. Massey jumped up to retrieve the pot, and she and Grayson joked about how he said he was backing off from the “hot, steaming water.” Massey then replied, “I rebuke you in the name of Jesus.”
Both Grayson and Farley drew their pistols and yelled at Massey to put the pot down. Grayson told investigators he thought her “rebuke” meant she intended to kill him and, in the following commotion, fired three shots, striking Massey just below the eye.
Farley testified that Massey didn’t say or do anything that caused him to view her as a threat. But under cross-examination, he acknowledged that he initially reported to investigators that he feared for his safety because of the hot water. Farley did not fire his weapon and was not charged.
Grayson, who was subsequently fired, testified in his own defense. He told jurors he noticed the bottom of the pot was red and he believed Massey planned to throw the water at him. He said Massey’s words felt like a threat and that he drew his gun because officers are trained to use force to get compliance.
“She done. You can go get it, but that’s a head shot,” Grayson told Farley after the shooting. “There’s nothing you can do, man.”
Grayson relented moments later and went to get his kit while Farley found dish towels to apply pressure to the head wound. When Grayson returned, Farley told him his help wasn’t necessary, so he threw his kit on the floor and said, “I’m not even gonna waste my med stuff then.”
Massey’s death forced the early retirement of the sheriff who hired Grayson and generated a U.S. Justice Department inquiry. The federal probe was resolved with Sangamon County Sheriff’s Department’s agreement to fortify training, particularly de-escalation practices; develop a program in which mental health professionals can respond to emergency calls; and to generate data on use-of-force incidents.
Massey’s family settled a lawsuit against the county for $10 million, and state lawmakers changed Illinois law to require fuller transparency on the background of candidates for law enforcement jobs.
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Want to opt out of AI? State labeling laws might help
Red STOP AI protest flyer with meeting details taped to a light pole on a city street in San Francisco, California on May 20, 2025.
Smith Collection/Gado/Getty Images
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Utah and California have passed laws requiring entities to disclose when they use AI. More states are considering similar legislation. Proponents say labels make it easier for people who don’t like AI to opt out of using it.
“They just want to be able to know,” says Utah Department of Commerce executive director Margaret Woolley Busse, who is implementing new state laws requiring state-regulated businesses to disclose when they use AI with their customers.
“If that person wants to know if it’s human or not, they can ask. And the chatbot has to say.”
California passed a similar law regarding chatbots back in 2019. This year it expanded disclosure rules, requiring police departments to specify when they use AI products to help write incident reports.
“I think AI in general and police AI in specific really thrives in the shadows, and is most successful when people don’t know that it’s being used,” says Matthew Guariglia, a senior policy analyst for the Electronic Frontier Foundation, which supported the new law. “I think labeling and transparency is really the first step.”
As an example, Guariglia points to San Francisco, which now requires all city departments to report publicly how and when they use AI.
Such localized regulations are the kind of thing the Trump Administration has tried to head off. White House “AI Czar” David Sacks has referred to a “state regulatory frenzy that is damaging the startup ecosystem.”
Daniel Castro, with the industry-supported think tank Information Technology & Innovation Foundation, says AI transparency can be good for markets and democracy, but it may also slow innovation.
“You can think of an electrician that wants to use AI to help communicate with his or her customers … to answer queries about when they’re available,” Castro says. If companies have to disclose the use of AI, he says, “maybe that turns off the customers and they don’t really want to use it anymore.”
For Kara Quinn, a homeschool teacher in Bremerton, Wash., slowing down the spread of AI seems appealing.
“Part of the issue, I think, is not just the thing itself; it’s how quickly our lives have changed,” she says. “There may be things that I would buy into if there were a lot more time for development and implementation.”
At the moment, she’s changing email addresses because her longtime provider recently started summarizing the contents of her messages with AI.
“Who decided that I don’t get to read what another human being wrote? Who decides that this summary is actually what I’m going to think of their email?” Quinn says. “I value my ability to think. I don’t want to outsource it.”
Quinn’s attitude to AI caught the attention of her sister-in-law, Ann-Elise Quinn, a supply chain analyst who lives in Washington, D.C. She’s been holding “salons” for friends and acquaintances who want to discuss the implications of AI, and Kara Quinn’s objections to the technology inspired the theme of a recent session.
“How do we opt out if we want to?” she asks. “Or maybe [people] don’t want to opt out, but they want to be consulted, at the very least.”
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