I Fought The Law And The Law…
A lawsuit bonanza: Kalshi vs. states, Baltimore vs. DraftKings/FanDuel, DC vs. PASPA, PA vs. DraftKings' promos, Florida compact dispute, and Lotto.com vs Texas Lottery.
The Bulletin Board
THE LEDE: A look at a handful of gambling-related lawsuits (not Kalshi) that range from interesting to bizarre.
ROUNDUP: PA interstate iPoker launch day; LA sweeps bill; Penn Board shakeup; Tax bill in OH; WY forms gambling committee; Reads of the Week.
VIEWS: The double-edged sword of political contributions.
AROUND the WATERCOOLER: Thoughts on the NCAA-Genius Sports deal.
STRAY THOUGHTS: Use your tools without hesitation, but not carelessly.
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The Lede: Gambling Continues To Come Under Legal Fire
The major story of 2025 (so far) is the legal battle between Kalshi and several states (latest updates here), but that isn’t the only legal battle occurring.
I recently covered a bizarre lawsuit brought against DraftKings and FanDuel by the city of Baltimore:
“The city of Baltimore is suing FanDuel and DraftKings, claiming the companies “employ sophisticated data analytics to identify and then exploit players showing signs of problem gambling,” which is exacerbated by bonus offers and VIP programs — the companies are licensed in the state of Maryland and comply with all regulations.”
And a DC lawsuit that claims the 2018 PASPA repeal doesn’t apply to Washington, DC:
“The District apparently thought that the Supreme Court’s New Jersey (PASPA) decision no longer applied to it. But that is wrong. The Tenth Amendment does not apply to the District of Columbia, so PASPA’s prohibition remains in full force in the District.”
The DC suit also tries to claw back winnings, using an old “recovery loss” statute on the books. But, as I said, “Before you dismiss it out of hand, a similar law was successfully used against PokerStars in Kentucky.”
There are now three more interesting lawsuits to add to the list.
PA Consumers vs. DraftKings
The first is a lawsuit filed in Pennsylvania that claims DraftKings’ promotional credits are difficult to understand and lure customers in by “falsely promising users that they will get free money which they can wager without any risk.”
Sportsbook advertising practices have led to lawsuits in several states, but the only one that has moved forward is a similar lawsuit in Massachusetts alleging DraftKings’ promotions are “unfair and deceptive.”
The new Pennsylvania suit goes on to say that “In reality, DraftKings has created an all-upside opportunity only for itself: the hidden terms of its promotions require users to deposit and gamble almost exclusively with their own money, which they almost always lose.”
Per SBC Americas, “The suit highlighted a 2023 promotion that offered a $2,000 deposit match bonus at DraftKings Casino.” The promotion required a 10x playthrough, which varied “based on which game users played, with table games like blackjack requiring a higher rate than something like slots.”
The lawsuit claims the bonus needed to be claimed in seven days:
“… assuming a hand of blackjack takes ~1 minute, a user betting $50 every hand would have to spend more than 66 hours in a seven-day period playing blackjack to satisfy the playthrough requirement. That amounts to almost ten hours of blackjack a day, without stopping to eat or go to the bathroom.”
As others have noted on social media, online blackjack is dealt at a much faster rate than the lawsuit purports (3- 4 times faster), but even at the accelerated rate, claiming the full bonus would require an inordinate amount of play.
Florida-Seminole Compact Round 2
The second suit comes from a group called “Protect The Constitution, LLC,” which has filed a lawsuit (h/t Daniel Wallach) claiming the 2021 compact between the Seminole Tribe and Florida violates Florida’s Amendment 3.
Amendment 3 was approved by voters in 2018 and requires a constitutional amendment to pass gambling expansions outside of tribal lands, which includes a 60% approval threshold through a ballot referendum. However, Amendment 3 explicitly says it does not affect the ability of Native American tribes, such as the Seminole Tribe, to negotiate compacts with the state for casino gambling on tribal lands, as IGRA governs these.
The question is, do the sports betting provisions in the 2021 compact qualify as on tribal lands?
The Bureau of Indian Affairs rules from 2024 expressly authorize Florida-style compacts that allow tribes to offer online gambling statewide, provided that it is authorized by the state and the person is not located on another tribe’s lands without that tribe’s consent.
“The Department proposed a new §293.22, clarifying that a compact may include provisions that are directly related to the operation of gaming activities. Congress… provided that a compact may include provisions relating to any other subjects that are directly related to the operation of gaming activities, including activities occurring off Indian lands.”
“… Accordingly, provided that a player is not physically located on another Tribe’s Indian lands, a Tribe should have the opportunity to engage in this type of gaming pursuant to a Tribal-State gaming compact. The Department notes that the ultimate legality of gaming activity occurring off Indian lands remains a question of State law, notwithstanding that a compact discusses the activity.”
Lottery Couriers vs. Texas
The final one is Lotto.com’s lawsuit against the state of Texas, stemming from an impromptu on-site visit to Jackpocket’s land-based retailer that led to lottery couriers being banned in the state.
As SBC Americas reports, “Lotto.com is seeking the Travis County court to intervene and stop former Texas Lottery Commission Executive Director Ryan Mindell’s new proposed rules that lottery couriers are no longer allowed in the state.” Mindell recently resigned from the Commission.
The lawsuit makes a crazy situation even crazier.
Roundup: PA Interstate iPoker; LA Sweeps Bill; Penn Board Changes; OH Tax Hike Is Back; WY Gambling Committee; Reads of the Week
WSOP.com confirms it will combine PA player pool today [Pokerfuse]: When it officially announced it had joined the Multi-State Internet Gaming Association (MSIGA), Pennsylvania regulators confirmed BetMGM Poker would combine its player pool with other MSIGA states on April 28. The big question was, what about WSOP.com and PokerStars? We know the answer for at least one, as last week, WSOP Online officially confirmed it would also be combining player pools. According to Pokerfuse, “A Pennsylvania Gaming Control Board (PGCB) spokesperson confirmed that WSOP will merge its Pennsylvania player pool on April 28, the same day BetMGM Poker is scheduled to launch tri-state shared liquidity.”
Louisiana anti-sweeps bill advances, sponsor disputes SPGA claims [Sweepsy]: A bill, SB 181, that would prohibit online sweepstakes sites has passed the Louisiana Senate Judiciary B Committee. The bill’s sponsor, State Sen. Adam Bass, called sweepstakes sites “illegal online casinos” masquerading as sweepstakes. Bass also disputed a claim by the Social and Promotional Games Association (SPGA) that the bill “endangers lawful businesses,” and could “unintentionally criminalize loyalty and rewards programs run by some of the most respected brands in the country.”
Penn board receives an overhaul [Earnings+More]: Penn has nominated two of the three board members proposed by activist investor HG Vora Capital Management (HG Vora owns approximately 5% of Penn stock), which has been critical of the company’s foray into online betting. Johnny Hartnett and Carlos Ruisanchez will join a board that is currently down to just seven members, with two more announcing they will not stand for reelection at the 2025 Annual Meeting of Shareholders. The third HG Vora choice, William Clifford, can run for one of the vacant seats.
Ohio has a “new” sports betting tax increase proposal [Local 12]: A “new” (the bill was introduced back in March) proposal from State Sen. Bill Blessing that would help fund stadium proposals would be financed by increasing the state’s sports betting tax rate from 20% to 36%. “Blessing and Governor Mike DeWine are advocating for a tax increase on sports bets. The governor's budget suggests doubling the tax from 20% to 40%, while Blessing's bill, SB 150, proposes a smaller increase to 36%. The additional revenue would be directed into a new fund to support arena and stadium projects.”
Wyoming creates new Select Committee on Gaming [Buffalo Bulletin]: Wyoming is exploring numerous gambling expansions, including online casinos. So far, these efforts have fallen flat. A new committee created by the legislature could help end gambling’s losing streak. Per local reporting, “The Management Council created the new select committee that will be entirely dedicated to studying gambling issues in Wyoming. There are six members on the committee, three from the House of Representatives and three from the Senate.”
Reads of the Week: A look at what STTP is reading.
Is It Time For The Minimum Age In All Gambling Markets To Be 21?, Valerie Cross, Sweepsy
Classifying Sports Betting Under CFTC is a Regulatory Gamble ~ Bruce Merati, GGB
Artificial Intelligence, Real Consequences: The Misguided War On AI In Sportsbooks ~ Jeff Edelstein, InGame
Ruddock Report: Politics, Prediction Markets Looming Factors In Legalization Efforts ~ Yours truly, Casino Reports
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Views: Above Board Political Contributions = Bad Optics
In today’s edition of damned if you do, damned if you don’t…
As Front Office Sports reported, “The two major sports betting companies, DraftKings and FanDuel, donated to Trump’s inaugural committee. DraftKings gave $502,000, while FanDuel provided about $482,000.”
A FanDuel spokesperson tells FOS that “participation at the inauguration is part of FanDuel’s regular government affairs activities. The inauguration provides FanDuel an opportunity to meet with state legislators from across the country in one place at the same time to discuss opportunities to collaborate on growing a legalized and regulated gaming market.”
For perspective, a total of $239 million was donated — combined, DraftKings and Fanduel contributed less than half of one percent of the total. Robinhood donated $2 million, while Miriam Adelson and Tilman Fertitta each donated $1 million to the Trump-Vance Inaugural Committee.
But those are not the only contributions making headlines.
Per reporting from Mississippi Today, DraftKings paid for, at least in part, an “unreported trip to the Super Bowl in New Orleans this year for House Speaker Jason White, his staff, and a couple of their spouses.”
There is nothing illegal alleged, as the article notes:
“Unlike many other states, Mississippi has no “gift law” banning or limiting how much money lobbyists or others can spend on politicians or government officials.
“In total, the Sports Betting Alliance, a group representing DraftKings and other gaming organizations, has spent approximately $454,000 since 2024 on lobbying fees and campaign donations to advocate for mobile sports betting, according to a review of campaign finance and lobbying reports.”
In a statement to Mississippi Today, a spokesperson said DraftKings “follows the required reporting requirements in all jurisdictions, including Mississippi.”
Still, the optics of this spending could result in more opposition, not to mention an easy attack vector for gambling opponents, which was previously exploited after a 2022 New York Times article that delved into lobbyist activity.
Around the Watercooler
Social media conversations, rumors, and gossip.
[Jerry Seinfeld voice] What’s the deal with the NCAA and Genius Sports?
The NCAA and Genius Sports made some waves last week when they announced a deal that will see the NCAA provide official data for its postseason tournaments to licensed sports betting operators.
The new deal builds upon a previous agreement reached in 2018. As David Purdum reports, in addition to the continued delivery of NCAA LiveStats, as part of the new arrangement (which runs through 2032), “The NCAA for the first time is authorizing licensed sportsbooks to use its marks and logos and receive official data from championship events, including the men's and women's basketball tournaments.”
One critic, Harry Levant (one of the architects of the SAFE Bet Act, and a guest on the STTP Talking Shop Podcast) wrote on LinkedIn:
And as others have pointed out, the NCAA appears to be sitting on both sides of the sports betting fence, as it has been arguing for prohibitions on prop bets on individual college athletes.
Or are they? There is an important caveat in the new deal. “Genius Sports will also collaborate with participating licensees to strengthen integrity protections and promote responsible betting practices, including limiting risky bet types, ensuring compliance and safeguarding student-athletes,” the press release reads.
As Purdum notes:
Stray Thoughts
The phrase “Don’t let perfect be the enemy of good” encourages entrepreneurs to act rather than wait for an elusive perfect moment.
When you endlessly tweak plans, await ideal market conditions, or over-polish products, you often miss opportunities.
Another way to think about this is like not using tools to prevent scratches. As I recently heard a Japanese sword master say about using katanas (the genesis of this entry btw), “If you’re going to fuss over every little scratch, you might as well hang them on a wall as a decoration.”
Inaction keeps tools pristine but useless. However, action must be thoughtful, not reckless.
Thoughtful action utilizes tools with purpose, accepting wear as a natural part of progress. This balance applies beyond entrepreneurship: a life spent avoiding risks is unlived. Resources gain value through use, and their scratches tell stories of resilience.
“Good enough” isn’t settling for mediocrity; it’s about creating something functional that can be refined through feedback and iteration. Unlike perfectionists, who seek control by avoiding uncertainty, those embracing the idea of “good enough” experiment and adapt. A scratched tool still works—a minimum viable product can still launch a business. Scratches, like mistakes, mark effort and growth, not failure.
While precision is essential in some fields, progress often involves calculated risks. So, use your tools intentionally. A scratched tool isn’t diminished; it’s proof you built something meaningful.