A third-party insurer placed five trades on prediction market Kalshi that match the exact $3 million figure LSU would owe Lane Kiffin in College Football Playoff bonuses.
Page F2From§Eachthe wee small hours edition — 2 September 2026
Insurance company bets $3 million on LSU, matching coach's bonus as Bill Simmons faces sports probe
When an insurance company places Kalshi trades worth up to $3 million on LSU's season, they're hedging their risk — or so the actuaries say. The exact sum matches Lane Kiffin's bonus, which is not a coincidence, it's a ledger entry. Meanwhile, Massachusetts authorities are reviewing Bill Simmons for proxy sports betting. The difference in treatment is not in the odds, but in the names on the ticket: institutional trades are business, individual bets are a violation. The state lines up the rules for one class, and the loopholes for another, and the gap is exactly the size of the premium that pays out. The books are balanced, but not for you. The column gap is your deductible, hon. The story is not the game, but who gets to play, and who gets paid. The ledger's got your name, but not your seat.
“The insurance guys are gambling millions on college football, and the same week, Massachusetts takes Bill Simmons to task for betting by proxy. One side gets a slap on the wrist, the other side gets a bonus. It's a rigged game, and the scoreboard's got your premium on it.”
“I don't see how this is a problem. Insurance companies have every right to hedge risk, and sports figures are just making the game more interesting. Bill Simmons is under review, but that's just due diligence. Did I say 'just'? Maybe it's more serious, but I wouldn't know.”
The receipts
Simmons, the founder of The Ringer, said Tuesday that it was a “lesson learned” after FanDuel voided his wagers.
This page is a back-issue: the story as it ran, receipts as they were. The current edition is at the front.