A two-decade-long friendship between prominent American podcasters and media personalities appears to have collapsed, reportedly over one man's public bitterness regarding his costly divorce settlement.
The End of an Era: A Friendship Unravels
Adam Carolla and Bill Simmons, whose professional and personal bond dates back to the early 2000s, are now estranged. The rift stems from comments Carolla made on social media about his ex-wife, Lynette Paradise, following their 2021 split. According to Paradise, Simmons was so disgusted by the online outbursts that he deliberately excluded Carolla from his annual Christmas party this year, a significant snub that signals a major breach.
The pair's friendship blossomed when Carolla became a regular guest on Simmons' various ESPN shows and subsequent podcasts, including those on Simmons' own platform, The Ringer. Their camaraderie was a fixture in the podcasting world, often featuring collaborations and public appearances together, including with fellow comedian Jimmy Kimmel.
The Financial and Personal Fallout
The core of the dispute lies in Carolla's divorce from Lynette Paradise. The financial terms of their 2021 separation were substantial. Carolla was required to pay Paradise a lump sum of around $4 million, alongside ongoing monthly spousal support of $32,000. He also paid $17,000 per month in child support for their twins, Natalia and Santino, though those payments have ceased now the children are 19.
Last month, Carolla vented his frustration publicly on X (formerly Twitter), stating he could not retire because he must continue working to support his ex-wife. "I had to give my ex wife my retirement account in the divorce," he posted. "I worked 30 years for that but I gave it to a person who chose not to work. Character is a big issue in this country." This post went viral and, according to Paradise, was the final straw for Simmons.
Friends Take Sides: The Party Snub That Said It All
Paradise discussed the incident on her podcast, For Crying Out Loud. She revealed that while attending Simmons' Christmas party, she was informed by mutual friend Melissa Iacono that Carolla was not invited. "Melissa's one of my closest friends and she's like, 'Yeah, they didn't invite Adam because Bill was disgusted by what Adam was doing on X'," Paradise recalled.
She later spoke directly with Simmons. "It got brought up and he was just like, 'Yeah, people don't wanna take sides in a divorce but this was just kind of such a turn off. I just didn't agree with it'," Paradise claimed Simmons told her. She expressed being "touched" by the show of support from some of their shared social circle.
The divorce itself was announced by Carolla on his podcast in May 2021 after 19 years of marriage. He stressed that infidelity was not a factor, describing it as a result of two people with "completely different processes and approaches to life." Despite his stated intention to make things work, the separation proceeded, culminating in the significant financial settlement and now, the collateral damage of a key friendship.
The Daily Mail has contacted representatives for both Adam Carolla and Bill Simmons for comment. The apparent end of this long-standing partnership marks a notable shift in the landscape of podcasting and entertainment circles, demonstrating how personal conflicts can spill over into professional relationships with lasting consequences.
