Jay Cutler, Madison LeCroy, & Kristin Cavallari’s Drama Is Messy — Here’s A Breakdown

If you’ve been on the internet in the past 72 hours, you’ve likely come across Jay Cutler, Madison LeCroy, and Kristin Cavallari’s drama. You’re also likely a bit confused because, well, it’s extremely confusing. So, I’m here to break it all down for you.

Before I dive in, a quick refresher: Cavallari and Cutler announced they were splitting after 10 years together on April 26, 2020. "With great sadness, after 10 years together we have come to a loving conclusion to get a divorce. We have nothing but love and respect for one another and are deeply grateful for the years shared, memories made, and the children we are so proud of," they wrote in matching Instagram statements. "This is just the situation of two people growing apart. We ask everyone to respect our privacy as we navigate this difficult time within our family."

Since then, things seem to get progressively messy between them with Cavallari publicly saying she thought about divorcing Cutler "every day" for two years before pulling the trigger and Cutler very publicly hanging with Cavallari’s nemesis Shannon Ford.

But then the drama with Madison LeCroy started and everything seemed to change. I’ll walk you through WTF went down below.

December 13, 2020: Cavallari is spotted hanging with Austen Kroll.

Cavallari and LeCroy’s ex Kroll first seemed to cross paths in October of 2020 when she and bestie Justin Anderson took a trip to Charleston. “She came to town with her friend Justin and the four of us [with Craig Conover] had dinner,” Kroll told Us Weekly on Nov. 29. “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.”

Then, this happened:

https://www.instagram.com/p/CIeI-TCJU2c/
https://www.instagram.com/p/CIeI-TCJU2c/

As promised, a week later Kroll and Conover made their way to Nashville. It was during that trip that dating rumors were officially sparked when an Instagram Live from a drunken night out featured Cavallari dancing atop Kroll’s shoulders as the crew danced to Taylor Swift.

BUT Cavallari quickly shut those rumors down when she posted a Dec. 14 Instagram Story that featured herself rolling her eyes alongside the caption, "I didn’t realize I wasn’t allowed to have FRIENDS that are guys."

January 8, 2021: Cutler is linked to LeCroy

A few weeks after the Kroll/Cavallari rumors first sparked, new rumors emerged about Cutler and LeCroy. “It’s nothing serious at this point,” a source reportedly told Us Weekly of LeCroy and Cutler’s rumored relationship on Jan. 8. “But they’re having fun getting to know each other.”

https://www.instagram.com/p/CJyxFPrra-P/
https://www.instagram.com/p/CJyxFPrra-P/

That same night, LeCroy seemed to fan the rumors that something was going on between herself and Cutler during an appearance on Andy Cohen’s Watch What Happens Live. When asked if she’d seen the Instagrams featuring Cavallari and Kroll dancing, LeCroy told Cohen she’d been "too busy" having her "own adventure" to pay attention to notice.

When Cohen asked if the "adventure" she was referring to involved Cutler, she seemed to hint that it did by replying, "I’m not kissing and telling, so…"

Jan. 22, 2021: LeCroy does a controversial Instagram Live.

OK, now here’s where things start to get messy. On Jan. 22, LeCroy went live on Instagram and reportedly threw some major shade in Cavallari’s direction. According to multiple comments from fans and also from Cavallari’s bestie Anderson, LeCroy made fun of the way Cavallari and Kroll were dancing together that one night.

https://www.instagram.com/p/CKeJJftBuUt/
https://www.instagram.com/p/CKeJJftBuUt/

It gets worse. In addition to the reported jab at Kroll and Cavallari’s dancing, the Bravo star also apparently claimed Cutler was "relieved" to have split from Cavallari and even apparently made some digs at Cavallari’s parenting.

Per BuzzFeed, LeCroy "jokingly shouted Jay’s name as though he was in the house."

So, yeah. I’m also cringing.

Jan. 23, 2021: Cutler and Cavallari break the internet.

In what many fans took as a direct response to LeCroy’s controversial Instagram Live, Cutler and Cavallari posted matching Instagrams that almost immediately broke the internet.

The posts in question featured them posing alongside each other with the caption, "the world is full of users. 10 years. Can’t break that."

https://www.instagram.com/p/CKXvyTlnyiG/
https://www.instagram.com/p/CKXvyTlnyiG/
https://www.instagram.com/p/CKXvyV8nqzq/
https://www.instagram.com/p/CKXvyV8nqzq/

LeCroy tried to involve herself a few times, but wasn’t quite able to get any response from Cutler or Cavallari:

https://www.instagram.com/p/CKY49MAMzrH/
https://www.instagram.com/p/CKY49MAMzrH/
https://www.instagram.com/p/CKZZqOnstnK/
https://www.instagram.com/p/CKZZqOnstnK/

Jan. 24, 2021: LeCroy drops reported receipts.

A day after Cavallari and Cutler broke the internet, LeCroy took to her Instagram Story to share what she claimed were receipts of conversations between herself and Cutler.

"It looks to me like I’m going to have to drop some receipts," she said in a video before posting the screenshots. "Hate to do that, but…"

She then went on to post screenshots. In the first, Cutler reportedly is trying to plan a trip to Charleston to come see her.

In the second, which seemed to be more recent, Cutler reportedly said he "didn’t appreciate" LeCroy mentioning his name publicly. While it’s not totally clear, he also reportedly said something was "insinuated" in addition to her saying his name. When she responded by saying "I respect you and I respect your family and I would never say anything to jeopardize your family," he responded "didn’t seem like that was the case."

Then she posted a selfie of them together:

She then went on to post the below bikini shot alongside the caption, "unbothered."

https://www.instagram.com/p/CKZaKS3rWO_/
https://www.instagram.com/p/CKZaKS3rWO_/

And this tanning shot alongside the caption, "Blocking more than the 🌞."

https://www.instagram.com/p/CKcXyoDLXlZ/
https://www.instagram.com/p/CKcXyoDLXlZ/

Later On Jan. 24: Anderson weighs in.

While Cavallari and Cutler kept quiet in response to LeCroy’s social media fire storm, Cavallari’s bestie Anderson had some words for the Southern Charm star. Apparently, he was the one who called LeCroy a "liar."

"The only time that I said anything and called someone a liar and said they were a snake was when they went live and talked about kids," he said. "That’s not right. I’m standing up for my friend." He continued, "Also, an adult posting private messages from another adult? That’s f*cking low. That says a lot right there."

https://www.instagram.com/p/CIwei3XFAfF/
https://www.instagram.com/p/CIwei3XFAfF/

As for Cavallari, she apparently could not care less. “All of what Madison is saying and putting out there is just noise to Kristin,” a source reportedly told Us Weekly on Jan. 25. “Kristin is unbothered by what is being said about her — it just doesn’t affect her in any way, to be honest.”

And no. Cavallari and Cutler are reportedly not back together. “There are no talks of Jay and Kristin getting back together,” a source reportedly told Us Weekly on Jan. 24. “They are just friends. Kristin is single.”

And that’s it! That’s a wrap on all of this drama. Well, for now.

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