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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.
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U.S. launches strikes in Syria targeting Islamic State fighters after American deaths
President Donald Trump and Defense Secretary Pete Hegseth salute as carry teams move the transfer cases with the remains of Iowa National Guard soldiers Sgt. William Nathaniel Howard, 29, of Marshalltown, Iowa, and Sgt. Edgar Brian Torres-Tovar, 25, of Des Moines, Iowa, and civilian interpreter Ayad Mansoor Sakat, who were killed in an attack in Syria, during a casualty return, Wednesday, Dec. 17, 2025 at Dover Air Force Base, Del.
Julia Demaree Nikhinson/AP
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Julia Demaree Nikhinson/AP
WASHINGTON — The Trump administration launched military strikes Friday in Syria to “eliminate” Islamic State group fighters and weapons sites in retaliation for an ambush attack that killed two U.S. troops and an American civilian interpreter almost a week ago.

A U.S. official described it as “a large-scale” strike that hit 70 targets in areas across central Syria that had IS infrastructure and weapons. Another U.S. official, who also spoke on condition of anonymity to discuss sensitive operations, said more strikes should be expected.
“This is not the beginning of a war — it is a declaration of vengeance. The United States of America, under President Trump’s leadership, will never hesitate and never relent to defend our people,” Defense Secretary Pete Hegseth said on social media.
The new military operation in Syria comes even as the Trump administration has said it’s looking to focus closer to home in the Western Hemisphere, building up an armada in the Caribbean Sea as it targets alleged drug-smuggling boats and vowing to keep seizing sanctioned oil tankers as part of a pressure campaign on Venezuela’s leader. The U.S. has shifted significant resources away from the Middle East to further those goals: Its most advanced aircraft carrier arrived in South American waters last month from the Mediterranean Sea.

Trump vowed retaliation
President Donald Trump pledged “very serious retaliation” after the shooting in the Syrian desert, for which he blamed IS. Those killed were among hundreds of U.S. troops deployed in eastern Syria as part of a coalition fighting the militant group.
During a speech in North Carolina on Friday evening, the president hailed the operation as a “massive strike” that took out the “ISIS thugs in Syria who were trying to regroup.”
Earlier, in his social media post, he reiterated his backing for Syrian President Ahmad al-Sharaa, who Trump said was “fully in support” of the U.S. effort.
Trump also offered an all-caps threat, warning IS against attacking American personnel again.
“All terrorists who are evil enough to attack Americans are hereby warned — YOU WILL BE HIT HARDER THAN YOU HAVE EVER BEEN HIT BEFORE IF YOU, IN ANY WAY, ATTACK OR THREATEN THE U.S.A.,” the president added.
The attack was conducted using F-15 Eagle jets, A-10 Thunderbolt ground attack aircraft and AH-64 Apache helicopters, the U.S. officials said. F-16 fighter jets from Jordan and HIMARS rocket artillery also were used, one official added.
U.S. Central Command, which oversees the region, said in a social media post that American jets, helicopters and artillery employed more than 100 precision munitions on Syrian targets.
How Syria has responded
The attack was a major test for the warming ties between the United States and Syria since the ouster of autocratic leader Bashar Assad a year ago. Trump has stressed that Syria was fighting alongside U.S. troops and said al-Sharaa was “extremely angry and disturbed by this attack,” which came as the U.S. military is expanding its cooperation with Syrian security forces.
Syria’s foreign ministry in a statement on X following the launch of U.S. strikes said that last week’s attack “underscores the urgent necessity of strengthening international cooperation to combat terrorism in all its forms” and that Syria is committed “to fighting ISIS and ensuring that it has no safe havens on Syrian territory and will continue to intensify military operations against it wherever it poses a threat.”
Syrian state television reported that the U.S. strikes hit targets in rural areas of Deir ez-Zor and Raqqa provinces and in the Jabal al-Amour area near the historic city of Palmyra. It said they targeted “weapons storage sites and headquarters used by ISIS as launching points for its operations in the region.”
IS has not said it carried out the attack on the U.S. service members, but the group has claimed responsibility for two attacks on Syrian security forces since, one of which killed four Syrian soldiers in Idlib province. The group in its statements described al-Sharaa’s government and army as “apostates.” While al-Sharaa once led a group affiliated with al-Qaida, he has had a long-running enmity with IS.
The Americans who were killed
Trump this week met privately with the families of the slain Americans at Dover Air Force Base in Delaware before he joined top military officials and other dignitaries on the tarmac for the dignified transfer, a solemn and largely silent ritual honoring U.S. service members killed in action.
The guardsmen killed in Syria last Saturday were Sgt. Edgar Brian Torres-Tovar, 25, of Des Moines, and Sgt. William Nathaniel Howard, 29, of Marshalltown. Ayad Mansoor Sakat, of Macomb, Michigan, a U.S. civilian working as an interpreter, also was killed.
The shooting near Palmyra also wounded three other U.S. troops as well as members of Syria’s security forces, and the gunman was killed. The assailant had joined Syria’s internal security forces as a base security guard two months ago and recently was reassigned because of suspicions that he might be affiliated with IS, Interior Ministry spokesperson Nour al-Din al-Baba has said.
The man stormed a meeting between U.S. and Syrian security officials who were having lunch together and opened fire after clashing with Syrian guards.
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Trump’s push to end transgender care for young people opposed by pediatricians
A display at the Gender Health Program of Children’s Minnesota hospital. Under a proposed rule announced Thursday, a hospital will lose all its Medicaid and Medicare funding if it continues to provide gender-affirming care for trans people under age 18.
Selena Simmons-Duffin/NPR
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Dr. Kade Goepferd watched the Trump administration’s moves on Thursday to ban gender-affirming care for transgender youth with “a mix of sadness and frustration.”
Goepferd, who is the founder of Children’s Minnesota Gender Health Program, says that for the medical community, nothing has changed about the evidence supporting gender-affirming care that could justify the government’s actions.

“There’s a massive propaganda and disinformation campaign that is selectively targeting this small population of already vulnerable kids and their families,” Goepferd says.
“Men are men”
Federal health officials said many times at Thursday’s announcement that their actions were driven by science and evidence, not politics or ideology. They frequently praised a report published by the Department of Health and Human Services in November. It concluded that clinicians who provide medical care to help youth transition have failed their patients and emphasized the benefits of psychotherapy as an alternative.
At times, health officials cast doubt on the idea that a person could be transgender at all.
“Men are men. Men can never become women. Women are women. Women can never become men,” said Acting CDC Director Jim O’Neill. He added that “the blurring of the lines between sexes” represented a “hatred for nature as God designed it.”
Health Secretary Robert F. Kennedy Jr. said doctors and medical groups had “peddled the lie” that these treatments could be good for children, and that those youth were “conditioned to believe that sex can be changed.”
Doctor groups disagree
The American Academy of Pediatrics, the medical group that represents 67,000 pediatricians across the country, pushed back forcefully on those characterizations.
“These policies and proposals misconstrue the current medical consensus and fail to reflect the realities of pediatric care and the needs of children and families,” said AAP President Dr. Susan J. Kressly in a statement. “These rules help no one, do nothing to address health care costs, and unfairly stigmatize a population of young people.”
AAP’s official position on this medical care is that it is safe and effective for the young people who need it. That view is shared by the American Medical Association, the Endocrine Society, among other medical organizations.
In a statement Thursday, the American Psychological Association wrote: “APA is deeply concerned about recent federal actions that not only challenge the scientific understanding of gender identity but also potentially jeopardize the human rights, psychological health, and well-being of transgender and nonbinary individuals.”
The most significant proposal released by HHS would withhold all Medicare and Medicaid funding from hospitals — a big portion of their budgets — if they provided gender-affirming care to those under age 18.
The Children’s Hospital Association said that rule — if finalized — would set a dangerous precedent. “Today’s proposed conditions make it possible for all kinds of specialized health care treatments to be withheld based on government-mandated rules,” wrote CEO Matthew Cook. “Millions of families could lose access to the care they need.”
After a 60-day comment period, the rules could be finalized and then take effect.
Attorneys general in New York and California have said they will fight these rules and protect the rights of trans people to get care in their states. The ACLU has vowed to sue, and more legal challenges are expected.
“I don’t want to be lost”
According to a CDC survey, about 3% of teenagers aged 13-17 identify as transgender, approximately 700,000 people. A poll from health research organization KFF found that less than a third of transgender people took medication related to their identity and 16% had had surgery.
For young people, medical options most commonly include puberty blockers and hormones. Surgery is very rare for minors. “This is health care that evolves over time, is individualized, tailored to a patient’s needs, often after years of relationship with a trusted health care team,” says Goepferd.
NPR spoke to a transgender 15-year old in California this week about the moves Trump administration officials were making to restrict care. “They think what I’m feeling is a phase and that my family should just wait it out and that it’s better I’m unhappy and never receive care,” he says. NPR agreed not to name him because of fears for his safety.
He says it can be difficult for those who are not transgender to understand that experience, but that, as far as he can tell, these health officials “are not interested in understanding trans people.”
He describes the long and deliberate process he made with his parents and doctors before he began taking testosterone. “The decision to not start gender-affirming care is often just as permanent as a decision to start it,” he says. “Not starting [hormone therapy], for some people, it feels like ruining our body, because there are certain changes we can never have.”
Now, after six months on testosterone, he feels like he’s on the right path, and is worried about the prospect of losing access to his medication if HHS’s efforts to shut down care nationally succeed. “It feels like someone’s throwing me into the bush just off the path I’m on, and that’s kind of terrifying,” he says. “I don’t want to be lost. I want to keep going where I’m going.”
“Deep moral distress”
More than half of states already ban gender-affirming care for young people after a frenzy of laws passed since 2021 in Republican-led states. This week, Republicans in the House led efforts to pass two federal bills that would restrict access to care, including one that could put doctors who provide the care in prison for up to ten years. It’s unclear if the bills will be voted on in the Senate.
Although nothing has officially changed in states where the care is still legal, these efforts to enact national restrictions have doctors and health systems in those states bracing for the possibility that their clinics will have to close down.
Dr. Kade Goepferd takes care of transgender and gender diverse young people at Children’s Minnesota hospital.
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“There’s a deep moral distress when you know that there is care that you can provide to young people that will measurably improve their health and the quality of their life, and you’re being restricted from doing that,” Goepferd of Children’s Minnesota says. “And there’s a moral distress in feeling like — as a hospital or a health care system — you have to restrict care that you’re providing to one population to remain financially viable to provide health care for other kids.”
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Takeaways from an eventful 2025 election cycle
Is there such a thing as an “off year” for U.S. elections? The elections in 2025 were not nearly as all-encompassing as last year’s presidential race, nor as chaotic as what is expected from next year’s midterms. But hundreds of elections were held in dozens of states, including local contests, mayoral races, special congressional elections and two highly anticipated governor’s races.
Many of the elections were seen as early tests of how lasting President Trump’s 2024 gains might be and as a preview of what might happen in 2026.
Here are five takeaways from the 2025 election cycle.
In Elections Seen as Referendums on Trump, Democrats Won Big
Democrats did well in nearly all of this year’s elections, continuing a pattern that has played out across off-year elections for the last two decades: The party that wins the White House routinely loses ground in the next round of elections.
The change in the final margin from the presidential election to the next election for governor
Virginia and New Jersey have historically swung away from the president’s party in governor’s races
Elections in these years are often viewed as referendums on the president’s performance. And Mr. Trump’s approval ratings, after months of holding steady, took a dip in November.
A notable shift came in New Jersey, where the majority-Hispanic townships that swung toward Mr. Trump in 2024 swung back to Democrats in the 2025 governor’s race. That contributed significantly to the victory of Representative Mikie Sherrill, the Democratic candidate, over Jack Ciattarelli, the Trump-backed Republican.
New Jersey’s majority-Hispanic towns snapped back left in 2025
Each line is a township whose width is sized to the number of votes cast in 2025
The leftward swing was viewed by many political commentators as a reaction to Mr. Trump. If that is the case, it remains to be seen how much of it will carry over into 2026.
Progressive and Moderate Democrats Are Both Claiming Victories
Democratic strategists continue to debate whether the party should embrace progressive candidates or more moderate ones. And in 2025, the election results had both sides feeling emboldened.
In New York City, Zohran Mamdani, a democratic socialist who struggled to garner support from the Democratic Party, defeated former Gov. Andrew Cuomo by nine points. A similar story played out in Jersey City, where James Solomon, a progressive, crushed former Gov. James McGreevey of New Jersey in a mayoral runoff. Progressives also prevailed in cities like Detroit and Seattle.
Centrist Democrats, meanwhile, came away with arguably the two biggest wins of the year against Trump-endorsed Republicans. Abigail Spanberger and Ms. Sherrill, both Democrats, outperformed their polling estimates and decisively won the high-profile governor’s races in Virginia and New Jersey.
The debate will continue among Democrats as several 2026 primaries have prominent progressive and moderate candidates going head to head.
In Texas, Representative Jasmine Crockett, a progressive, entered the primary race for a U.S. Senate seat against the more moderate James Talarico. A similar situation has developed in Maine, where Graham Platner has pitched himself as a more progressive alternative to Janet Mills in the party’s attempt to unseat Senator Susan Collins, a Republican. Other progressives, like Julie Gonzales in Colorado and Brad Lander in New York, are challenging incumbent Democrats in primary races.
A Record 14 Women Will Serve as Governors in 2026
Virginians elected Ms. Spanberger as their first female governor. In New Jersey, Ms. Sherrill became the second woman to secure the position. Both women significantly outperformed Vice President Kamala Harris’s margins from the 2024 presidential race, improving on her results by almost 10 points.
Female candidates also did well down the ballot. Eileen Higgins will be the first female mayor in Miami after defeating Emilio González, who had the support of Mr. Trump. And, in Seattle, Katie Wilson defeated the incumbent mayor, Bruce Harrell.
States that will have female governors in 2026
Come 2026, a record 14 women — 10 Democrats and four Republicans — will serve as governors, with six of them expected to run for re-election next year. (More than a dozen states have yet to elect a female governor.)
In New York, it is likely that both candidates will be women: Representative Elise Stefanik, a Republican, began a campaign last month against the incumbent, Kathy Hochul.
Special Elections Are Still Very Special (for Democrats)
Despite not flipping any House seats, Democrats outperformed Ms. Harris’s 2024 results in every House special election this cycle. Their wins, however, offer limited insight into what might happen in 2026.
Special elections, which happen outside of regular election cycles to fill vacated seats, draw fewer voters than those in midterm or presidential years. Special election voters tend to be older and highly engaged politically, and they are more likely to be college educated. That has given Democrats a distinct advantage in recent years, and 2025 was no exception.
Democratic candidates in this year’s special congressional elections outperformed Kamala Harris’s 2024 margins.
Democrats did well in the 2025 special elections
Democratic strength in special elections extended to lower-profile races held this year. In Virginia, Democrats secured 64 out of 100 seats in the House of Delegates. In Georgia, Democrats won two seats on the Georgia Public Service Commission, the first time the party won a non-federal statewide office since 2006. Pennsylvania Democrats swept the major Bucks County contests, electing a Democratic district attorney for the first time. And, in Mississippi, Democrats broke the Republican supermajority in the State Senate.
Odd-Numbered Years Are Still Very Odd (for Election Polls)
Polling in off-year election cycles is challenging because it’s hard to know who will turn out to vote. This year, the polls significantly overestimated the Republicans in the Virginia and New Jersey governor’s races, which both had particularly high turnout for an off year. In 2021, polls had the opposite problem, as they overestimated Democrats.
Each dot is a poll from the relevant governor’s election, positioned according to its polling error in the election.
Polls missed in opposite directions in 2021 and 2025
Polling misses don’t necessarily carry over from cycle to cycle: Despite the leftward bias of the polls in 2021, they performed very well in 2022. After each election, pollsters look at the result and evaluate their performance, and then note where they went wrong. Analysis from groups like the American Association for Public Opinion Research frequently indicates that errors come from an incorrect sense of who shows up to vote. Pollsters then try to adjust for this error in the next election cycle.
The errors of 2025 may prove largely irrelevant, however, as the midterm elections will feature a larger, very different pool of voters with a new set of races, and a new host of lessons for pollsters to learn.
Off years are weird, and the polling errors they produce often are as well.
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