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Did Whitney Cummings just throw some subtle shade at Grace O’Malley’s old boss? Fans definitely think so.
The debut episode of O’Malley’s “Disgraceful” podcast launched on Thursday, February 20, with Cummings, 42, as her first guest. O’Malley, 26, joked with Cummings about trying to find a cohost for the show, quickly poking fun at the elephant in the room (her past podcast with ex-BFF Brianna “Chickenfry” LaPaglia).
“We should either be cohosts or friends, maybe not both,” Cummings said. O’Malley replied, “That’s a great idea.”
Cummings joked, “I would rather be your cohost than your friend. I have loved being your friend, I love you dearly, but Mommy’s got bills. So, let’s end our friendship because working with friends, it, maybe, doesn’t go so well.”
O’Malley wondered where to “draw the line” between friendship and business, asking if texting was on the table.
Related: Grace O’Malley Addresses ‘Whirlwind’ Year in Brianna Chickenfry Friendship
Grace O’Malley has entered the chat. The Barstool Sports podcast host spoke out after continued questions about her friendship with Brianna “Chickenfry” LaPaglia. “Now that I have your attention: This last year & however many has been quite the whirlwind for Brianna and I’s friendship. Yes. There’s no denying that,” O’Malley, 26, shared via Instagram […]
“Maybe, schedule a Zoom. Maybe a slack and HR to be there,” Cummings said. “Oh HR, OK so, you don’t know what this is. HR it is an office where if you are being mistreated by your boss or maybe, like, publicly discussed by an older man and having the details of your life and emotional traumas exploited, you can go to someone and be, like, help.”
O’Malley replied, “That can’t be real.”
Cummings continued the joke as both women laughed.
Whitney Cummings. Cindy Ord/Getty Images
“You know what’s wild? It’s common that most people complain there’s too much of it,” she said. “But you have had none of it. But this is something that … protects employees.”
TikTok users were quick to clip this discussion from the podcast episode — which occurred within the first three minutes — and claim that Cummings was subtly (or maybe not) referencing O’Malley’s past with Barstool Sports.
O’Malley previously cohosted Barstool’s “PlanBri Uncut” podcast alongside LaPaglia. The women had a falling out late last year, which O’Malley confirmed via Instagram Stories in December 2024. LaPaglia then went on her other show, the “BFFs Podcast,” to discuss what went down between them while she was in an apparent abusive relationship with singer Zach Bryan.
“I really needed her, so I couldn’t do the podcast anymore because we’re sitting there pretending to be friends,” LaPaglia claimed in December 2024. “I didn’t feel seen by her. I needed to set a boundary.”
Earlier this year, O’Malley appeared on “This Past Weekend w/ Theo Von” and discussed her time at Barstool, hinting that LaPaglia made more than her.
“I didn’t make anything when I was there. I had a salary and that was kind of it,” she alleged. “I had the option to leave and I took it.”
Related: Barstool Employees Who’ve Detailed Salaries and Contract Negotiations
Getty Images (3) Barstool Sports is (almost) always making headlines for something — and they are arguably well-paid to do just that. Grace O’Malley announced her departure from the company in December 2024 after a friendship breakup from longtime bestie Brianna “Chickenfry” LaPaglia (more about that, here) and has since spilled the tea on what […]
Barstool founder Dave Portnoy, who had continuously weighed in on the drama between O’Malley and LaPaglia, made a social media video breaking down O’Malley’s salary at the media company. (Portnoy has also said multiple times that Barstool does have HR.)
“She was in the last year of a 3-year deal,” he explained in January, noting that her base salary was $175,000, and she apparently made 70 percent “of anything that we were able to sell on her personal socials.”
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He wondered if the interview was “cut up” or “misconstrued” but wanted to set the record straight.
“It does bother me when people make it seem like they’re not getting paid fairly,” Portnoy added. “I think we treated — as I’ve said from the beginning — Grace great.”
O’Malley has since left Barstool and launched her “Disgraceful” podcast with the Unwell Network.
