Don't cross Bill Simmons.
Page S2From§Eachthe matinee edition — 11 September 2026
Bill Simmons, under investigation for proxy betting, puts a colleague on his 's--t list' for skipping the show.
Hot Mic Moment
A man can excommunicate a colleague from his own broadcast in the time it takes to say the words, and the agency licensed to police his own gambling needed nine days just to open a folder on him. That gap is not bad luck. Somebody on the political desk should be asking why the public body charged with enforcing Massachusetts gambling law moves slower than a podcast host settling a personal grudge. Get me the political desk.
Gushis side
This reporter has covered a great many workplace disputes, rarely with the theatrical fury Bill Simmons brought to his own microphone Thursday. Simmons, host of the top podcast on his ESPN network, announced that colleague Peter Schrager, absent for a scheduled appearance, now sits "on my s--t list." A banishment, delivered live, over a missed taping.
Brand-new trouble, this reporter assumed, for a host who runs his operation on loyalty and access — until the paperwork corrected that assumption, too. Massachusetts gaming regulators, this reporter had understood, opened their file on Simmons's own betting just this week, a coincidence of timing almost too tidy to print.
The commission's interest, this reporter is given to understand, centers on a friendly wager Simmons had a family member place on his behalf — the sort of favor that keeps a sports-talk empire running warm between segments.
Two files, then, on one man. The s--t list moved in the time it takes to record an intro. The gaming file has sat open nine days and counting, one man's discipline outrunning the state's.
Trudyher side
Wrong network, Gus — Simmons hasn't hosted for ESPN in years. That show runs on The Ringer, the site he founded, now owned by Spotify. Doesn't soften the s--t list any, just fixes who's cutting the checks.
Try again. The Massachusetts Gaming Commission opened that file September 2nd — nine days before Thursday's episode aired. Whatever's brand-new around here, sugar, it isn't the paperwork.
Not a favor — a rule. Massachusetts bars using a proxy to place your own bets, full stop. Simmons told his own audience he asked his daughter's boyfriend to do it. That's the violation the commission's file is about, not a bonding exercise. Take a nap before the next taping; you'll hold the facts better rested.
Settle down, hotshot — the political desk covers appropriations bills, not podcast beef. But you landed the paper trail by accident: the commission's own docket lists Simmons's file opened September 2nd, still open as of Thursday's show. Go lie down. Mushrooms for that memory wouldn't hurt either.
“This is a guy who can end somebody's career segment on live mic before lunch, and it took the state of Massachusetts nine days just to open a folder on his own bets. That's not two separate stories, that's the same guy — fast with the power, slow to face any of it himself. The s--t list is free; the accountability's on backorder.”
“Look, a host curating his own guest list is just professionalism — old-fashioned, actually. And the gaming commission thing, that's routine, every bettor who names a proxy gets a look, happens all the time — did I say "all the time"? I mean it's procedural, nothing to see. Bill's just protective of his show, that's not a pattern, that's not a — why would that be a pattern.”
The receipts
· Massachusetts Gaming Commission investigating Bill Simmons proxy bets from the morgue, 2 Sep 2026
This page is a back-issue: the story as it ran, receipts as they were. The current edition is at the front.