The Latest Breaking News from Bill Simmons

Prediction markets have become America’s new national pastime

My parents’ generation may have been on to something when they railed against gambling. If only George Santos had listened

The Guardian - US · Sep 6

Bill Simmons’s embrace of ChatGPT is a breach of his website’s creative spirit

The founder of The Ringer and Grantland was famous for discovering and developing writers. Now he is promoting a technology eroding the creative industries

The Guardian - US · Sep 3

Portland Trail Blazers Moving to to St. Louis? Here's What Kalshi Prediction Market Says

The Portland Trail Blazers relocation rumors opened a relocation market on Kalshi.

Sports Illustrated · Aug 5

Meghan Markle Branded 'Boring' As Expert Savages Duchess's New Lifestyle Business

Journalist Marina Hyde has savaged Meghan Markle's As Ever lifestyle brand as 'b******t' and 'boring', arguing on her podcast that the Duchess and Prince Harry keep recycling the same royal‑exit story.

International Business Times UK · Mar 27

The NFL’s Greed Never Ceases to Amaze

The league is reportedly unhappy that NBC is paying more money to the NBA.

Sports Illustrated · Feb 12

Bill Simmons Had Perfect Response to Mat Ishbia Pointing Out Suns Hit the Over

Bill Simmons and Mat Ishbia continued their odd social media feud.

Sports Illustrated · Feb 12

Bill Simmons Rips Tom Brady for Saying He’s Not Rooting for Patriots in Super Bowl LX

Simmons, like a lot of Patriots fans, couldn't believe what he heard from Tom Brady this week.

Sports Illustrated · Feb 5

5 sports podcasts every fan should add to their lineup in 2026

These are the sports podcasts I'm listening to

Tom’s Guide · Feb 4

Podcaster sparks fresh Taylor Swift pregnancy rumors while blasting Travis Kelce

The singer and NFL star were engaged in August after two years of dating

Evening Standard · Dec 23, 2025

Taylor Swift Pregnancy Rumours: Sports Podcaster Drops Cryptic Comment About Singer, Travis Kelce

Bill Simmons recently made a cryptic comment about Taylor Swift and Travis Kelce. He said that the couple is having a baby, and his remark caused confusion among fans.

International Business Times UK · Dec 23, 2025