Bill Maher’s Hot Take: Cassie’s ‘Devil’s Deal’ with Diddy Exposed
Can’t wait to see how *this* one unravels. On the latest episode of HBO’s Real Time on May 30, Bill Maher leveled a sarcastic broadside at singer-model Cassie, insisting she “could have left” Sean “Diddy” Combs but instead opted for what he cynically dubbed a “devil’s deal.” According to Maher, Cassie’s refusal to walk away from her former partner is less about love and more about power plays—yes, even if she claimed she was the injured party in their public legal tussles.
Maher’s comments weren’t plucked from thin air. He pointed to court documents filed in December 2023 (Entertainment Tonight) showing Cassie’s attempt to sue Diddy for alleged emotional distress. Yet here we are, years later, hearing that she’s still tethered to Combs in one form or another. “She had her shot to exit stage left,” quipped Maher, “but why do that when you can keep the perks rolling?” His punchline: signing a confidentiality clause in exchange for a big fat settlement is basically signing up to ride another round on the Diddy roller-coaster.
If you thought the reception would be polite applause, think again. Rolling Stone flagged pushback from fans who argue Maher’s quip downplays the seriousness of Cassie’s claims. Meanwhile, Page Six notes that insiders close to the case say Cassie’s priority was never money—it was safety. But Maher doubled down, insisting any woman who sticks around after reading a contract deserves a “front-row seat to the circus.”
For those keeping score at home, TMZ first broke the news of Cassie’s lawsuit back in December, and People Magazine later confirmed details of the settlement talks. Yet Maher’s roast on Monday night painted a different picture: he framed Cassie as a willing participant in her own PR saga, as if walking away were as simple as stepping off a set. Spoiler alert: real-life drama is rarely that neat.
And yes, there’s more: Maher teased that if Cassie truly wanted out, she could have campaigned publicly for her freedom—no hush money required. That, he said, would have been “the ultimate mic drop.” But instead, Cassie signed on the dotted line. Devil’s deal or savvy negotiation? You decide.
So there you have it—another celebrity feud gets the sardonic Bill Maher treatment. Tune in next week when he’ll probably roast someone else for making a supposedly “stupid” choice. Nothing shocking here, folks. Let’s all act surprised.
Sources: Celebrity Storm and TMZ, Entertainment Tonight, Rolling Stone, People Magazine
Attribution: Creative Commons Licensed
