DraftKings and Sportsbook Giants Are Targeting State Legislators Who Support Stricter Betting Rules

A new investigative report from WBUR has documented how DraftKings, FanDuel, and Fanatics have pooled $43 million into a super PAC called Win For America that is actively targeting statehouse legislative races in states where stricter sports betting regulations are under consideration. The effort represents an escalation of the online sports betting industry’s political strategy as a wave of states that legalized betting in recent years now wrestles with reform proposals driven by lawmakers who have come to regret their original votes.

DraftKings contributed $19.5 million to the super PAC, nearly half its total funding, according to Federal Election Commission records. Win For America operates by channeling funds through smaller state-level PACs with names like American Conservatives Fund that obscure their connection to the gambling industry, making it difficult for voters to identify who is paying for local political advertising. DraftKings CEO Jason Robins confirmed the strategy publicly, describing it as an experiment the company plans to evaluate after this cycle.

The Massachusetts Battleground

The sharpest current confrontation is in Massachusetts, where state Senator John Keenan has filed the Bettor Health Act, one of the most aggressive sports betting reform proposals in the country. The bill would restrict advertising, more than double the tax rate on sportsbook revenues, and ban proposition bets, which are wagers on individual player performances or in-game micro-events. Keenan publicly apologized for his 2022 vote to legalize sports betting and described the industry’s growth as having exceeded what he anticipated.

DraftKings executives and family members donated $17,750 to re-elect House Speaker Ronald Mariano and $19,800 to Representative Aaron Michlewitz, the chair of the House Ways and Means Committee, during the same period the Bettor Health Act was advancing through the Senate. DraftKings is headquartered in Boston. For the bill to become law, it needs a House floor vote, which requires approval from both Mariano and Michlewitz. The legislative session ends in July.

WBUR found the super PAC has spent money in at least 11 states over the past several months. In some states, the spending targeted races involving lawmakers trying to expand sports betting. In others, it funded negative campaigns against legislators backing stricter regulations, including prop bet bans and advertising restrictions.

The Broader Reform Wave

Massachusetts is not an isolated case. Colorado passed a reform package in March that included restrictions on deposit frequency and marketing limits, though the proposed prop bet ban was stripped out before passage. A similar Louisiana bill died after concerns about lost tax revenue. In nearly a dozen states, lawmakers who originally voted for legalization have introduced reform legislation citing problem gambling concerns, advertising saturation, and the growth of high-risk bet types.

The industry’s political spending reflects a calculation that preserving the status quo in key markets is worth substantial investment. The specific focus on statehouse races, rather than federal lobbying, acknowledges that sports betting policy remains primarily a state-level fight and that individual legislative relationships carry enormous influence in relatively small political environments where money goes further.

For bettors in states like Massachusetts, the outcome of these political battles will directly determine which bet types remain available and what tax framework supports the market. A prop bet ban in Massachusetts would eliminate same-game parlays and player prop markets from licensed sportsbooks, affecting the offerings at DraftKings, FanDuel, and every other operator in the state. The combination of legislative momentum and industry pushback makes the path forward for reform bills uncertain, but the political pressure on both sides is intensifying.