Good overview of the gambling tax rule that has went in effect this year.
It is insane, unfair, senseless, and all kinds of other adjectives. Well placed people have told me it will go away. But they’ve been telling me that for a year and it is still there.
A Massachusetts man bet $12,950 on a hole DraftKings accidentally created in its own system. It paid him $934,147.83. DraftKings tried to cancel most of it. Regulators said no.
– On October 15, 2025, during Game 3 of the MLB ALCS between the Toronto Blue Jays and Seattle Mariners
– A DraftKings trader misclassified Blue Jays outfielder Nathan Lukes as a "non-participant" in the company's internal trading system.
– That error disabled the safeguard meant to stop customers from stacking correlated versions of the same bet into one parlay.
– It meant a bettor could combine Lukes' hit totals, 5+, 6+, 7+, and 8+ hits in the series, all inside a single ticket, each leg priced as if it were independent.
– A Massachusetts customer found the gap and placed 27 parlays totaling $12,950, several of them padded further with unrelated college football and NFL favorites.
– Lukes finished the seven-game series with nine hits. Twenty-four of the 27 parlays hit.
– DraftKings owed him $934,147.83.
– DraftKings froze the tickets and asked the Massachusetts Gaming Commission for permission to void most of it
– Offering to pay roughly $96,000 instead and calling the bettor's actions "unethical."
– On December 18, 2025, the commission rejected that argument outright, noting the error was entirely internal to DraftKings, not caused by any outside data feed.
– One commissioner put it plainly: "It's the cost of doing business."
– The vote was unanimous, 5-0. DraftKings was ordered to pay the full $934,147.83.
He found a hole DraftKings built into its own system, bet directly into it, and won. DraftKings tried to rewrite the outcome after the fact. Regulators told them the mistake was theirs to keep.
You should be thrown in prison if you play music off of your phone for everyone to hear during a red eye flight to Europe while everyone is trying to sleep. #FUCK
Thank you @RepTroyNehls for supporting the FAIR BET Act. This is a simple bipartisan fix that just needs to get done.
Stop dragging your feet, @SpeakerJohnson and @RepJasonSmith, and restore the 100% tax deduction for gambling losses.
https://t.co/PUVANdd9L9
. @queencityspx yoooooo, good Sunday evening. Would absolutely love it if we didn’t have teams pulling with with 4-5 pro hoopers not on their roster in the low rec division, preeesh in advance