The feud began on Sunday after Hill amplified a 2016 clip from Barstool Sports' "The Rundown" where Portnoy compares then-San Francisco 49er quarterback Colin Kaepernick to an "ISIS guy" and says he looked "Arabic."
"This is terrible, but then again, consider the source," Hill reacted.
After retweeting screenshots of Barstool's coverage defending Kaepernick over the years, Portnoy retaliated by retweeting a screenshot from a 2009 tweet written by Hill which was labeled "transphobic" by the Twitter user.
"My fb friends are calling him 'Manny the Tranny'... so inappropriate and hilarious," Hill wrote. Her tweet was in reference to former MLB player Manny Ramirez's doping scandal, where he used a female fertility drug as a steroid.
Supporters of Portnoy went after Hill on social media, using the hashtag #CancelJemele, which trended on Twitter.
The Barstool Sports CEO said he was not going to apologize or "bend the knee" for his remarks about Kaepernick, which he said was "literally a joke from 'The Office'" and how the people who want to cancel him probably "love" the show but "hate" him.
-READ MOREEmergency Press Conference - Cancel Culture Is Coming For My Head pic.twitter.com/FS3SCMd0BP
— Dave Portnoy (@stoolpresidente) June 29, 2020