Overlapping Payments Reveal Rep. Mike Lawler’s Deep History As A Political Operative

NEW YORK — Advocacy and political groups controlled by Rep. Mike Lawler paid more than $720,000 to the political consulting firm he co-founded, a comprehensive review of public records by POLITICO shows.

The arrangement is not illegal, according to ethics watchdogs, but it raises conflict of interest questions from his past as the Republican House member seeks reelection in one of the most competitive battleground seats in the country.

Lawler, a co-founder of the political consulting firm Checkmate Strategies, owned a 50 percent stake in that business and has directed advocacy-oriented nonprofits, political committees and campaigns for public office that paid it for its services. Lawler sold his stake in Checkmate Strategies last year, a deal he said netted him up to $50,000, according to a personal financial disclosure form filed in August.

POLITICO has previously reported that Lawler’s campaigns paid his former firm $500,000 for campaign services. A new analysis of other campaign finance and lobbying records shows that in addition to those payments, before entering Congress, Lawler directed a host of organizations that paid a combined total of at least $221,515 to Checkmate for its services between 2019 and 2021.

Before his time in the House, Lawler honed his skills as an operative working as a lobbyist, political consultant and party boss. But the lines between the three roles often blurred together — a reality that now poses a political liability as Democrats eye his suburban congressional seat as a prime pickup opportunity this year.

Lawler founded Checkmate Strategies in 2018 with Chris Russell, a political operative who now serves as his campaign spokesperson. Two years before Lawler divested from the firm in 2025, he valued his stake in the business at 50 percent.

When Lawler served as director of the natural gas advocacy group New Yorkers for Affordable Energy, it paid Checkmate Strategies $97,000 to lobby for it in 2019 and 2020, with Lawler listed as the group’s individual lobbyist. When he led the economic development group 17 Forward 86, the organization paid Checkmate $95,000 for lobbying over the same time period. And when Lawler was chair of the Orangetown Republican Committee, it paid Checkmate over $26,000 for campaign mailers and consulting in 2019 and 2021.

Government watchdog groups suggested the payments to Lawler’s former political firm from the organizations he directed were improper and called for such financial arrangements to be prohibited.

“These kinds of self-dealing transactions should be banned,” said Rachael Fauss, a senior policy advisor with the group Reinvent Albany. “No nonprofit board or political committee should allow their leadership to enter into contracts with another entity they have a financial stake in. Unfortunately, attempts to rein this in have failed for decades."

Russell responded by attacking Reinvent Albany, saying that its board president, Aaron Naparstek, founded a pro-transit news outlet that criticized Lawler’s opposition to congestion pricing in New York.

“The so-called ‘ethics watchdog’ is actually an organization run by a pro-congestion pricing, left-wing Democrat who endorsed Zohran Mamdani and has a well-documented history of attacking Congressman Lawler on social media,” Russell said in a statement. “It is well known that prior to being elected to Congress, Mike was a political consultant. Political consultants get paid to consult on campaigns.”

“Reinvent Albany does not endorse candidates and whatever genius, blather or endorsements that Naparstek posts on his social media feed are his alone,” the group’s executive director, John Kaehny, said in a response to Russell.

Cait Conley, a candidate in the Democratic primary vying to unseat Lawler, questioned whether Lawler entered politics to benefit himself.

“This is exactly what people hate about politics and why they're losing faith that government will actually solve their problems: career politicians and political consultants who make money for themselves and their friends instead of actually solving the problems of their community,” Conley said in a statement. “The Hudson Valley deserves a public servant, not a political operative.”

Russell insisted that his boss “has never profited from his time in public office, and has fully disclosed everything.” He also attacked Conley, pointing to reporting from POLITICO that found she worked for AI firms that did business with the Department of Homeland Security and Palantir.

“Conley’s credibility is shot and her campaign is imploding because of it,” Russell said. “Frankly, we appreciate her stupidity for bringing even more attention to it with this baseless attack.”

Lawler declined to be interviewed for this article.

The payments to Checkmate from a web of organizations Lawler controlled show the Hudson Valley Republican’s deep experience as an operative, a fact that continues to be made clear as Lawler meddles in the Democratic primary for his battleground seat.

Earlier this month, Team Lawler sent a covert text message blast to Democratic voters. The text was an apparent attempt to sow discord in their crowded primary, and its sender was only revealed when respondents replied “HELP” to the message. The next week, Lawler taunted the chair of the Westchester Democratic County party online after the organization opted against endorsing in the race. And a few days later, his campaign manager filed an unsuccessful lawsuit to kick an underdog Democratic candidate off the primary ballot.

In March, POLITICO reported that Darrell Davis, a Black activist from Westchester, has quietly been on Lawler’s campaign payroll since June 2024, usually netting $2,000 a month from the campaign. That fact wasn’t disclosed in a video Davis filmed in support of Lawler’s previous reelection campaign or when his civil rights group issued a statement defending Lawler after pictures emerged of him dressed up as Michael Jackson with his face darkened.

Davis told POLITICO the payments from Lawler’s campaign had nothing to do with his decision to endorse Lawler or defend him publicly. Lawler’s campaign said that “the inference that an African-American community leader and activist who supports a Republican must be bought and paid for is insulting and, frankly, racist.” Davis remains on Lawler’s payroll.

Beyond lobbying, the Orangetown Republican Committee, which Lawler acted as chairman of from 2017 to 2022, also reported paying Lawler $1,319.18 personally for “fundraising” in 2021 — but that payment was not reported by the House member in his 2022 candidate financial disclosure form. Federal ethics disclosure rules require candidates to report income over $1,000 from a single source. Lawler’s campaign maintains the payment was not income, but a reimbursement for DJ, audio and awards expenses related to party functions, which would not need to be disclosed on federal ethics and financial disclosure forms.

Republican candidates in Orangetown also paid Checkmate thousands of dollars for campaign services. Around the same time, Lawler’s Orangetown Republican Committee expressed public support for those same candidates.

In addition to his former role as chairman of the Orangetown Republican committee, Lawler serves as chairman of the Rockland County Republican Party, giving him outsize power over candidates in town elections around New York’s Hudson Valley.

Last spring, the Rockland Republican Party held its annual Lincoln Day Victory Ball. The event, held at the Pearl River Hilton, was advertised as a fundraiser for the county party on WinRed, the Republican party’s national fundraising platform. But after POLITICO contacted Lawler’s campaign with questions about the fundraiser and irregularities in the Rockland County Republican Party’s campaign finance filings, WinRed’s webpage tied to the event was deleted. It was republished online shortly after POLITICO asked Lawler's campaign why the page was taken down.

By law, Lawler, who attended the fundraiser, cannot solicit contributions for state and local elections if those donations don’t also comply with federal rules. Still, committee filings show one business and one labor group donated to the county party in connection to the fundraiser — two groups federal candidates are not permitted to solicit contributions from.

Russell told POLITICO that Lawler “did not solicit contributions on behalf of the Rockland County GOP” at the event. Photos from the event show the House member speaking behind a lectern displaying a party logo with his name on it and presenting awards to two of the night’s featured speakers.

Contributions to the Rockland County Republican Party from the day of the fundraiser were first filed in the county party’s housekeeping account, according to filings with the state board of elections. But four months later, the Rockland County Republican Party amended its financial filings to record donations from that fundraiser under the party’s main campaign account. The county party also removed records of contributions from the day of the fundraiser from its housekeeping account.

According to New York election law, contributions to housekeeping accounts can be unlimited, but funds in housekeeping accounts may only be used for expenditures unrelated to “the express purpose of promoting the candidacy of specific candidates.” The fundraising page for the Lincoln Day Victory Ball describes the event as a benefit for the Rockland County Republican Committee, and makes no mention of a housekeeping account.

Russell told POLITICO that “the monies in question were deposited into the correct bank account, but it was allocated to the wrong account on the original filing.”

“When that error was self-caught, the organization filed an amended report to correct it,” he added.

He also said the WinRed webpage from the event was taken offline because the Rockland Republican Party is preparing to republish it with updated information on this year’s Lincoln Day Victory Ball fundraiser.

Daniel Weiner, director of the Brennan Center for Justice’s Elections and Government Program, told POLITICO that federal candidates like Lawler are “not allowed to solicit funds that do not comply with federal law for federal elections.”

“The question really is, ‘Was he soliciting donations that don't comply with federal law?’” Weiner said. “That would probably mean, in this case: ‘Was there some sort of explicit indication that he was not soliciting such donations?’ For example, a very clear statement in his remarks, or some kind of sign?”

Lawler’s campaign refused to say whether he told fundraiser attendees he wasn’t soliciting contributions outside of federal rules, and only said he never asked for any party money.