A Maryland filing shows only $2.7 million going out. Federal records show nearly all the rest moved to other PACs, and state records show that one of them, American Future, spent against five Republican legislative candidates weeks before the election.
By Michael Phillips | MDBayNews
Win for America, the political group financed by the online sportsbook industry, registered with Maryland election officials on Sept. 29. Two days later, it filed a report listing $80.65 million in donations and one expenditure: $2.7 million sent to a Texas political committee, with a note saying it was “not specifically for MD activity.”
The Maryland report alone leaves most of the money unexplained. Win for America’s federal filings do not. They show that almost all of it was passed to other committees, and that the group had less than $1 million left on Sept. 30.
One of those committees is American Future, which has been spending in Maryland since May. State records downloaded Oct. 17 show it has reported $3,672,627.82 in independent expenditures, including $1,470,003.35 since Sept. 24. In every general-election race where the records show both sides, the money supports the Democrat and opposes the Republican. A second committee, Win for America funds, the American Conservative Fund, received far more of its money nationally. A search of Maryland’s independent expenditure records on Oct. 17 found no transactions attributed to it.
“The Maryland report alone leaves most of the money unexplained. Win for America’s federal filings do not.”
What the Maryland filing shows
Win for America (Maryland Filer ID 16020352) is a participating organizations committee. Its Statement of Organization was approved Sept. 29 and amended Sept. 30 to change its resident agent. Jeremy Kudon is listed as principal officer and Brian Smith as treasurer, both at 3301 Richmond Highway, Suite 1018, in Alexandria, VA. The treasurer’s listed email address is americanconservativefund@gmail.com.
Smith signed the 48-hour report on Oct. 1 at 3:24 p.m. It covers Nov. 18, 2025, through Sept. 30, 2026, and lists four donors:
- DK Crown Holdings Inc., Boston: $39.15 million across nine payments.
- FanDuel Inc., New York: $27 million across six payments.
- Hillside (Shared Services US) LLC, Evesham, N.J.: $8 million across three payments.
- FBG Enterprises OpCo, LLC, New York: $6.5 million across three payments.
The payments add up to $80.65 million. The largest single payments were $6.5 million each from DK Crown and FanDuel in January. The most recent was $2.5 million from Hillside on Sept. 18.
The filing does not name the companies behind those entities, but public records do. Public Citizen lists DK Crown Holdings Inc. as DraftKings. The Massachusetts Gaming Commission’s licensing decision identifies FBG Enterprises Opco, LLC as “Fanatics” or Fanatics Betting and Gaming. A New Jersey Division of Gaming Enforcement order lists Hillside (Shared Services US) LLC as a wholly owned affiliate of the bet365 Group.
The only expenditure is a Sept. 30 transfer of $2.7 million to American Future, a committee with a Dallas address. The report categorizes it as a transfer to Maryland-registered political committees and describes it as a contribution “not specifically for MD activity.”
Where the money went
Win for America is also a federal super PAC, registered with the FEC on Nov. 5, 2025 (committee ID C00925586). Its FEC summary, covering Nov. 5, 2025, through Sept. 30, 2026, shows:
- $81.65 million in total receipts, all categorized as individual contributions.
- $80.70 million in total disbursements.
- $77.45 million in contributions to other committees.
- $945,508 in cash on hand.
- $0 in independent expenditures.
In other words, Win for America does not buy ads itself. It funds other committees that do. Beyond the $77.45 million sent to other committees, it reported $2.25 million in operating expenditures and $1 million in contribution refunds to individuals or persons. Its FEC summary lists no direct independent expenditures and $945,507.64 in cash on Sept. 30.
“In other words, Win for America does not buy ads itself. It funds other committees that do.”
The itemized FEC records available through June 30 show where most of the operating money went. Summit Management and Strategy LLC of Falls Church, Va., received $1,656,782.63 in 23 payments, listed as management, communications, strategy, and compliance consulting. Click Strategies of Los Angeles received $120,000 for communications consulting. The records do not say who owns or runs either firm.
The FEC receipt total is $1 million higher than the Maryland report’s $80.65 million, and the earlier FEC start date does not explain it. The itemized FEC receipts through June 30 total $72 million: DK Crown $34 million, FanDuel $27 million, Hillside $5.5 million, and FBG $5.5 million. The first of them is dated Nov. 18, 2025, the same day the Maryland report’s window opens. The Maryland report adds $8.65 million after June 30 (DK Crown $5.15 million, Hillside $2.5 million and FBG $1 million), which brings it to $80.65 million. The FEC reports $1 million more in gross receipts than the Maryland filing, even though both show contributions beginning Nov. 18, 2025. The FEC also separately reports a $1 million contribution refund, but the available records do not establish whether the two are related. The FEC’s post-June itemization was not reviewed for this article. The discrepancy remains unresolved.
Reporting through June 30 shows who received the money:
- American Conservative Fund, the Republican-side vehicle, received at least $50.6 million from Win for America through June 30, according to the Daily Caller’s review of FEC data. The fund’s own FEC summary shows $51.59 million in receipts and $50.29 million in disbursements for Nov. 18, 2025, through June 30.
- American Future, the Democratic-side vehicle, received $17.45 million through June 30, per the Daily Caller. Its FEC summary shows $17.52 million in receipts, $14.50 million in disbursements, and $3.02 million in cash on June 30. Its treasurer is listed as Cassie Tinsmon, and its mailing address, 3723 Greenville Ave., Suite 41077, Dallas, matches the Maryland payee.
- Georgia drew the most attention. Reuters, as cited by Covers, reported more than $12 million in Georgia state races. The Daily Caller reported $8.5 million from the American Conservative Fund and $3.4 million from American Future in Georgia, where sports betting is not legal.
- In Michigan, two new super PACs created in July, Michigan Conservative Fund and America’s Future, list DK Crown Holdings and FBG Enterprises as their only donors and spent nearly $3 million on 15 legislative races, according to Bridge Michigan, cited by Civic Media.
Put plainly, the larger share of Win for America’s money went to the Republican-side vehicle. Maryland has been a Democratic-side story. A search of Maryland’s independent expenditure records on Oct. 17 found no transactions attributed to the American Conservative Fund. The email address listed for Win for America’s treasurer on its Maryland registration, americanconservativefund@gmail.com, names the fund. The Baltimore Banner reported June 17 that American Future had spent close to $1.9 million in Maryland’s Democratic primaries, according to state records. Baltimore Brew reported June 16 that Win for America moved $4.75 million to American Future between May 21 and May 29 for those races. The FEC’s itemized records confirm those transfers: $750,000 on May 21 and $2 million each on May 27 and May 29. They also show the American Conservative Fund received $4.5 million from Win for America in the same window ($500,000, $2 million, and $2 million).
“Put plainly, the larger share of Win for America’s money went to the Republican-side vehicle. Maryland has been a Democratic-side story.”
One open question remains. Brew’s $4.75 million in May transfers to American Future do not appear in the new Maryland report, which lists only the $2.7 million. The two figures should not be added together as Maryland spending until the overlap is resolved. Maryland’s independent expenditure records do not list contributions received by American Future, and the FEC itemization reviewed ends June 30, so the Sept. 30 transfer cannot yet be matched to a federal receipt.
Why the Maryland report looks thin
The State Board of Elections’ campaign finance guide says a participating organization’s report must list each disbursement made in the state and each disbursement made to influence a state election. Spending in other states does not belong in it. Donors of $10,000 or more cumulatively during the reporting period must be identified, and the first report must reach back two years from the filing date.
The guide also says an organization must register within 48 hours after making more than $6,000 in political disbursements in an election cycle, and that qualifying disbursements include money sent to out-of-state committees that spend in Maryland. American Future was spending in Maryland’s June primaries, and the Banner and Brew reported it was funded by Win for America. Win for America’s Maryland registration was approved Sept. 29, while American Future’s own registration as an independent expenditure entity was approved May 20. Why the Win for America registration came then, and which committee made the earlier transfers, is not answered by any record reviewed. Those records do not establish a violation.
“Those records do not establish a violation.”
The primaries
Brew reported that the American Future ads it reviewed did not mention gambling, and the Banner reported the attack ads were not tied to the targets’ gambling votes. Among the details reported:
- Nearly $290,000 in positive ads for Senate President Bill Ferguson, according to the Banner.
- More than $360,000 against Del. Frank Conaway Jr., according to Brew. Conaway is among the sponsors of HB 1226, the Maryland Illegal Online Gambling Enforcement Act, which would have prohibited knowingly operating or promoting illegal online gambling. The bill, whose Senate companion was SB 652, passed the House 135-1 on March 23 and did not become law. As introduced, the bill defined an online gambling operator as someone running a site used for illegal online gambling, and excluded persons licensed to conduct online sports wagering or fantasy competitions. The text read at second reading kept that exclusion in the definition and added a separate one saying the subtitle does not apply to those licensees. MDBayNews did not independently confirm the House-passed third-reader text.
- Brew reported the PAC also spent $30,000 supporting Sen. Guy Guzzone, who chairs the Senate Budget and Taxation Committee, where HB 1226 stalled, and was unopposed in the primary.
Those are facts about timing and targets, and the reporting does not say the spending was tied to any vote. A voter can still reasonably ask why gambling money was spent in a race where gambling never came up in the ads. Gambling Insider characterized the network’s Illinois and Pennsylvania spending as defensive, aimed at proposed or existing tax increases on sports betting, and its Georgia and Texas activity as a push in states without legal sports betting. That is the reporter’s characterization, not a statement from the group. Win for America declined to comment on its Maryland activity to the Banner. In April it told Axios it supports candidates who will “thoughtfully approach regulation.”
The general election
The Baltimore Banner’s Rick Hutzell reported Oct. 16 that American Future has spent $3.2 million this year on General Assembly races, including $289,000 in the District 30 race. The state’s independent expenditure records, downloaded Oct. 17, include filings made after that column. They show $3,672,627.82 in reported spending since May 18, across 136 transactions, and $346,221.25 against Jessica Haire alone in District 30. About $2.20 million of the total was spent through the June 23 primary. The other $1,470,003.35 came after it, and all of it began Sept. 24, with $596,271.34 that day, followed by steady 48-hour reports through Oct. 14.
Payees for the post-primary spending:
- The Pivot Group, Inc., Washington, direct mail: $561,125.00.
- Sway, Chevy Chase, online advertising: $552,969.00.
- Targeted Platform Media, LLC, Crownsville, television: $333,358.35.
- GPS Impact, Des Moines, other expenses: $22,551.00.
The state’s records break each payment down by candidate. Since Sept. 24, the general-election spending adds up this way:
- Jessica Haire, opposed: $346,221.25. The Banner identifies her as the Republican challenging Democratic Sen. Shaneka Henson in District 30. Henson is listed as supported for $4,785.00.
- Stephanie Popescu, supported: $297,850.78. She is the Democrat in the District 42 Senate race.
- Raj Goel, opposed: $214,330.18. Mary-Dulany James, the Democrat in the District 34 Senate race, is supported at $31,836.82.
- Barry Beauchamp, opposed: $212,754.22. Josh Hastings, the Democrat in House District 38B, is supported at $40,786.95.
- Stuart Schmidt, opposed: $163,227.62. Chuck Cook, the Democrat in House District 33B, is supported at $2,677.00.
- Kevin Ford, opposed: $155,533.53, in the same District 42 Senate race as Popescu.
In every pairing the records show, the money supports the Democrat and opposes the Republican. American Future’s Maryland independent expenditure reports list no donations received during the periods covered. These are independent expenditures, meaning money spent to influence elections, not money paid to the candidates. The dates are transaction dates, not the dates the reports were filed. The records do not say why these districts were chosen or what the group wants from any of these races.
“In every pairing the records show, the money supports the Democrat and opposes the Republican.”
On the primary side, the same records show $342,468.21 supporting Senate President Bill Ferguson, $404,310.28 opposing Hasan Jalisi, and $312,864.78 opposing Del. Frank Conaway Jr. Those totals do not match the earlier Banner and Brew figures exactly, and the records do not explain why. Jalisi’s office and party were not confirmed for this article. The newer filings also include supportive spending for a long list of Democratic legislative candidates, none of whom is listed as a target.
Two details are worth flagging. First, nine transactions totaling $153,879.87 carry dates of May 18 and May 19, before American Future’s registration was approved May 20. The Statement of Organization was e-signed May 18, and the state’s records do not say whether registration is required before spending is reported. Second, one May 18 mailer is listed as opposing Molly McKee-Seabrook, while every other McKee-Seabrook line is listed as support. That may be a data-entry error.
Hutzell wrote that the group appears aimed at improving the odds that future lawmakers will vote to legalize online casino games, a different policy question from both legal sports betting and HB 1226’s enforcement against illegal sites, and noted that no one for American Future responded to a request for comment. Senate President Bill Ferguson’s spokesperson told the Banner that outside groups make their own spending decisions and that Ferguson has no involvement in directing them.
The Board of Elections’ public profile for American Future also lists an $8,000 civil penalty for failure to file an independent expenditure report, assessed June 12, 2026, with the status unpaid and open at the time their profile was reviewed. American Future’s principal officer is listed as George Wellde 3rd and its treasurer as Cassie Tinsmon, both at the Dallas mailbox address. Its Maryland contact email and the resident-agent contact on Win for America’s Maryland registration both use the domain katzcompliance.com, which suggests the two groups use the same compliance firm. The filings do not say so directly.
Who is Jeremy Kudon
Jeremy Kudon became chairman of the Sports Betting Alliance in December 2025 after eight years as its president, according to Legal Sports Report. He is also the principal officer listed on Win for America’s Maryland registration. The alliance’s members are bet365, BetMGM, DraftKings, Fanatics and FanDuel, which overlap with Win for America’s funders.
What to watch
- American Future’s next 48-hour reports, which are due within two days of each new spending event through Nov. 3, and whether the American Conservative Fund ever shows up in Maryland.
- Whether Win for America’s $2.7 million Sept. 30 transfer shows up in American Future’s reports as received money. The Maryland independent expenditure records reviewed list no donations in the periods covered.
- Win for America’s next federal report.
- Whether the Maryland report is amended to show the May transfers to American Future, and what the Board of Elections says about the late-September registration.
- Whether the $1 million difference between the FEC and Maryland receipt totals is explained, and whether it relates to the $1 million refund line.
- Why the race selection: why Districts 30, 33B, 34, 38B and 42, and whether the group has said what it wants from them.
- What the 2027 General Assembly does with online gambling enforcement after HB 1226 stalled in the Senate.
MDBayNews has previously covered Maryland gaming regulators and the casino lobby in “Maryland’s Gaming Regulators Let the Casino Lobby Write Their Homework,” published July 12.
Sources: Maryland State Board of Elections, Win for America (Filer ID 16020352) 48-Hour Report filed Oct. 1, 2026, and Statement of Organization approved Sept. 29, 2026 (amended Sept. 30); Maryland State Board of Elections, Campaign Finance Summary Guide, Chapter 6, section 6.3; Maryland General Assembly, HB 1226 (2026), bill page; Maryland State Board of Elections, American Future (Filer ID 16020173) Statement of Organization (approved May 20, amended Sept. 23, 2026), 48-Hour Reports filed Oct. 9 and Oct. 16, 2026, and public committee profile; Maryland State Archives, Maryland Manual 2026 House of Delegates and Senate candidate lists; Rick Hutzell, “Online gaming PAC accentuates the negative in Maryland state Senate race,” The Baltimore Banner, Oct. 16, 2026; Federal Election Commission itemized receipts (Schedule A) and disbursements (Schedule B) for Win for America, exported Oct. 17, 2026; Maryland State Board of Elections, Independent Expenditure Reported by Filer and Expenditure downloads for American Future, Oct. 17, 2026; Maryland General Assembly, HB 1226 (2026), as introduced and as read at second reading; Federal Election Commission committee summaries for Win for America (C00925586), American Future (C00926204) and American Conservative Fund (C00927186), reviewed Oct. 17, 2026; Massachusetts Gaming Commission, FBG Enterprises Opco, LLC final licensing decision; New Jersey Division of Gaming Enforcement, order licensing Hillside New Jersey LLC d/b/a bet365 NJ; Nathan Bomey, “Exclusive: DraftKings, FanDuel, Fanatics, Bet365 fund sports gambling super PAC,” Axios, April 9, 2026; Chavdar Vasilev, “DraftKings, FanDuel Funnel $41M Into Win for America PAC Targeting Multiple States,” Gambling Insider, April 16, 2026; Mark Reutter, “Sports betting interests are pouring unregulated money into Maryland Democratic races,” Baltimore Brew, June 16, 2026; Mark Reutter, “Another PAC backed by iGaming money bets big on Bill Ferguson,” Baltimore Brew, June 18, 2026; Pamela Wood, The Baltimore Banner, June 17, 2026; Rick Claypool, Public Citizen, June 30, 2026; Grant Mitchell, “Sports Betting Companies Spend $72M on US Midterms,” Covers, July 28, 2026; The Daily Caller, “Sports Betting Industry Playing Its Hand In 2026 Elections,” Aug. 31, 2026; Civic Media, “Sports gambling super PACs place big bets on Michigan legislative races,” Aug. 1, 2026; Matthew Waters, “Sports Betting Alliance Adds Maloney, Kudon Shifts To Chairman,” Legal Sports Report, Dec. 11, 2025.
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