Kristin Cavallari, Jay Cutler and Madison LeCroy Drama: A Timeline
If only Kristin Cavallari and Jay Cutler were down to move to Charleston and join the cast of Southern Charm for season 8. The former couple have gotten involved in Madison LeCroy and Austen Kroll’s messy split — and Us Weekly is breaking down the drama timeline.
Cavallari, 34, and Cutler, 36, announced their split in April 2020 after a decade together and seven years of marriage. The twosome, who share sons Camden, 8, and Jaxon, 6, and daughter Saylor, 5, were involved in a brief custody battle before agreeing to split their time with their kids 50/50.
Several months later, Cavallari made headlines for hanging out with Kroll, his costar Craig Conover and her bestie Justin Anderson in Charleston.
“She came to town with her friend Justin and the four of us [with Craig] had dinner,” Kroll told Us Weekly about their friendship in October 2020. “We’ve all been in contact ever since. We’re in this, like, big old group chat, and the group chat is active. We had a blast with them and I’m gonna take a trip to see them in Nashville sometime soon.”
LeCroy, for her part, joined the cast of Southern Charm for season 6 in 2019 after she started seeing Kroll. The twosome continued to document their on-again, off-again relationship during season 7 before they called it quits for good in December 2020.
“We are not together right now. I am 1,000 percent single, and so is he,” LeCroy exclusively told Us at the time. “So, ladies, if you want him, you can have him.”
That same month, the hairdresser, who shares 8-year-old son Hudson with her ex-husband, also commented on Kroll’s friendship with the Hills alum.
“I think he’s trying to get under my skin, which is fine. And, like, honestly? If he can pull her, go for it. Knock yourself out. I’d be shocked,” LeCroy told Entertainment Tonight in December. “I just think it was just trying to get [a rise], get a comment out of me — and he did.”
Kroll, meanwhile, told Us that he and his ex were no longer on speaking terms after watching the season back. (The Southern Charm season 7 finale aired on January 21 and the cast taped the reunion in mid-December.)
“What you’re seeing [on TV] happened back in May, June, July. People assume that we broke up yesterday,” he said on December 16. “It’s like I cut off my addiction cold turkey. It just hasn’t been easy.”
Scroll through for a timeline of the drama: