Bill Simmons has long covered the NFL mostly through the lens of gambling. But over the past few years, his Million Dollar Picks segment has really put his punditry to the test.
The man who put out a Friday column picking the games against the spread for years may have lost a step. Even he admits it.
Recapping Week Eight of the NFL season on Sunday night with weekly cohost Cousin Sal Iacono, Simmons teased that he may have to retire the segment because the timing isn’t right. It could be the timing, or that he just keeps losing.
“I’ve had it making picks on Thursdays. I might just dump Million Dollar Picks and come up with some different gimmick where I pick games on Sunday,” Simmons said. “You have the Chiefs in a tease and then it’s, ‘Mahomes might not play, if he plays he’s sick.'”
“I made my bet on Million Dollar Picks on Thursday, I bet the real game on Tuesday. Now he’s sick?”
https://twitter.com/rbillsimmonspod/status/1718954879626960948?s=46&t=td4ZnRYfgyBaXXaNadwnkw
Simmons fans have long complained about the segment, which typically is done solo and likely is required as part of his and The Ringer’s partnership with FanDuel. (Iacono hosts separate gambling-centric NFL shows for The Ringer and FanDuel TV.)
Mahomes and Kansas City lost to the Broncos for the first time in eight years on Sunday, and the offense looked lethargic while Mahomes battled a bug.
But even before this week’s Mahomes-Chiefs uncertainty, Simmons was already off to a painful start to the NFL season.
Bill Simmons is currently down $854k in “Million Dollar Picks”
He may not be able to buy that 7th Malibu Beach House
Onto Week 8! pic.twitter.com/Zt9frmeFyb
— The r/BillSimmons Podcast (@rBillSimmonsPod) October 27, 2023
The idea basically is that Simmons works with a $1 million pool trying to make money over the course of the year with an assortment of bets. It’s an improvement on the many columnists and hosts who just pick the games with minimal setup. But it’s certainly not great content when the bets are losing this hard.
If the sharps, his fans, and Simmons himself are all in alignment that it’s time to move on, the time is probably right. Thank you, Patrick Mahomes?
[The Bill Simmons Podcast, @rBillSimmonsPod on X]
About Brendon Kleen
Brendon is a Media Commentary staff writer at Awful Announcing. He has also covered basketball and sports business at Front Office Sports, SB Nation, Uproxx and more.