Capitol Park in Augusta with the Maine State House in the background. (Joe Phelan/Staff Photographer)

A billionaire CEO from Illinois gave gobs of cash to back a conservative candidate and a transgender athlete referendum in Maine this election cycle. The donations did not lead to success.

Dick Uihlein and a political group he funds gave nearly $6 million in total to back Republican gubernatorial candidate Garrett Mason, and to the proposed referendum to ban transgender students from participating in sports or using changing rooms in a way that aligns with their gender identity.

Mason finished fourth in June’s crowded primary. The referendum likely will not appear on November’s ballot after it ran into legal challenges over petition signatures.

Uihlein and his wife, Liz, founded the shipping and packing supplies firm Uline in 1980. Though he is far from the only megadonor on either side of the political spectrum to financially support Maine candidates and causes, his contributions were notable because of how much he spent on a state to which he has no clear connection — and how little he got back on his investments.

Most of Uihlein’s contributions came through his role as the top donor to the conservative Restoration of America PAC, which used a Maine offshoot this cycle to lead all other Maine committees in raising and spending. In all, it spent about $5 million on ads and materials supporting Mason, per the state campaign finance database. (PACs cannot directly coordinate with candidates.)

He also gave $800,000 to the Safeguard Girls Sports committee that helped lead the transgender student-athlete petition drive in Maine which ultimately hit a snag in court. He was the largest donor to the committee. Restoration of America PAC also gave it $50,000 in April, and a Conservative Agenda for America group previously linked to Uihlein gave it $100,000 in June, per campaign finance records.

Uihlein, 80, has reportedly been the biggest donor to the Florida-based Restoration of America PAC for years, giving it $57 million in just the last year and a half, from the start of 2025 to this past June. Another megadonor, Tom Klingenstein, who chairs a California-based conservative think tank, gave the PAC’s Maine operation $3 million to help Mason and has previously backed Maine Republicans.

Uihlein has no clear ties to Maine. He and his wife own homes in Illinois and Wisconsin. Their corporation is headquartered by the Illinois border in Pleasant Prairie, Wisconsin. Whether he will continue to direct money to the Pine Tree State after this year is an open question.

Other billionaire donors of varying ideologies who get involved in Maine politics tend to have ties to the state known for its annual surge in summer residents and tourists. The most prominent one has been conservative legal titan Leonard Leo, who has a Northeast Harbor home and has donated to a variety of Republican-backed initiatives.

Leo also hosted a 2019 fundraiser for U.S. Sen. Susan Collins. In a consequential campaign finance case, a dark money network tied to Leo is backing a lawsuit attempting to overturn a 2024 initiative that Maine voters approved to place a $5,000 cap on super PAC contributions.

Uihlein, a descendant of the former Schlitz Brewing dynasty, and his wife rarely speak to the media, and he did not respond to requests for comment sent through a Uline media relations line and via Restoration of America.

But they are undeniably influential in political and philanthropic circles, with prolific giving to President Donald Trump and a 2018 headline in The New York Times dubbing them, “The Most Powerful Conservative Couple You’ve Never Heard Of.”

“I’m a conservative,” Uihlein said in a 2013 interview. “I’m for free speech, free markets, not just limited government but smaller government, the Second Amendment and the sanctity of life.”

He has taken big swings on Republicans like Trump who have enjoyed electoral success, and he has also seen his money fail to produce victories in other states. Uihlein gave at least $4 million to back a 2023 anti-abortion effort in Ohio that around 60% of voters there rejected. He topped $50 million to support Illinois Republican Darren Bailey in his failed 2022 gubernatorial bid.

Uihlein and Restoration of America PAC failed to push Mason, who aligned himself with Trump and hired a top ally of Vice President JD Vance to manage his gubernatorial campaign, to the top of the GOP gubernatorial primary in Maine this year. Mason, 41, an evangelical Christian who also ran for governor in 2018, finished well behind other Republicans like Jonathan Bush and Bobby Charles in fundraising and at the ballot box.

But Restoration of America went big on pro-Mason ads. Those ads touted Mason as supporting police, cracking down on illegal immigration and standing with Trump to stop transgender girls from competing in girls sports.

Charles, a Leeds attorney who worked under several past presidential administrations, used a flurry of lower-budget, AI-infused social media ads to effectively bill himself to Republican primary voters as an outsider who will shake up Augusta while bashing Mason as an insider.

Charles and other GOP candidates weren’t afraid to go after Mason for benefiting from Uihlein’s money, and Mason was not afraid to say he embraced it.

“I think that any conservative should be happy that there’s a large conservative activist who sees promise in Maine and sees that there’s a foothold here, that we can make life better for people,” Mason said in March.

Uihlein’s sizable contributions to Mason and the transgender athlete-focused referendum effort still matter, even if they didn’t produce immediate success, said Bela Sullivan, a policy and research associate at Issue One, a Washington-based group that aims to reduce the influence of money in politics.

“It does shape the type of policies and issues that get put in front of Maine voters,” Sullivan said.

Supporters of the transgender athlete-focused referendum have said they intend to keep working to get the measure before voters. A pending lawsuit in federal court argues that the Maine Department of the Secretary of State should not have invalidated more than 1,000 signatures.

The pro-referendum side funded by Uihlein vastly outspent the anti-referendum campaign that only used $75,000 and included groups supportive of LGBTQ+ rights. The three Maine residents who challenged the petition signatures had help, though, from the powerful Elias Law Group, a Democratic-aligned firm based in Washington, D.C.

Leyland Streiff, a Brunswick resident and leader of the Protect Girls Sports in Maine committee that is continuing to push for the referendum, nodded to polling showing a majority of Mainers support keeping female transgender student-athletes out of female sports. The referendum is “certainly moving forward,” and it is not a question of if it will go before voters, Streiff added.

“The question is simply when,” he said.

As for the Uihlein-backed Restoration of America PAC, Streiff said he hopes it “continues to support our efforts to end sex-based discrimination in Maine’s schools.”