Home Latest A Timeline Of The Kristin Cavallari, Jay Cutler, and Madison LeCroy Drama

A Timeline Of The Kristin Cavallari, Jay Cutler, and Madison LeCroy Drama

If you’ve been living under a rock, you may have missed the messiest celebrity feud of 2021 yet. And it all involves some of the biggest names in reality TV. Madison LeCroy, Austen Kroll, Kristin Cavallari, Jay Cutler, and Justin Anderson have all found themselves in a nasty social media war, and it’s been confusing, to say the least.

It’s been nine months since the former NFL player and clothing line CEO announced their divorce plan, which was equally as messy. So the fact that not even a year later, their former partnership being brought up again in another nasty battle isn’t too surprising. What is shocking is that it all started over another reality star and her ex-boyfriend basically doing a couple swap. However, this has been a long lead-up to get to where we are now, and many people are confused about what is even going on.

But first, here is a guide to important people in the drama:

  • Kristin Cavallari & Jay Cutler: famous exes and co-stars of Very Cavallari
  • Justin Anderson: Kristin’s best friend and hairstylist/former Very Cavallari co-star
  • Madison LeCroy & Austen Kroll: famous exes and stars of Southern Charm

Here’s a timeline of Kristin, Jay and Madison’s feud:

October 2020

Cavallari and Kroll first met and hung out back in October 2020 at a dinner with mutual friends. And when it became known on social media, LeCroy commented “Hate [that] I couldn’t see you guys!” on Anderson’s post. Nothing strange here, right?

November 2020

Cutler was seen having lunch with his ex-wife’s former “UncommonJames” employee and Very Cavallari co-star, Shannon Ford, in Charleston. The two ladies notably didn’t get along, and they’ve had a history of bad blood since. LeCroy commented, “See y’all soon” on Cutler’s post. People were more surprised that Jay was hanging out with Shannon, and it was perceived to be a big fat “f-you” to Cavallari — no one paid attention to Madison.

December 5, 2020

Kristin posted a steamy bikini photo to her Instagram. Madison, Austen’s ex, commented on the photo, “See you next week. Keep breaking the internet in the meantime.” Soon after, popular Instagram page @commentsbycelebs posted a screenshot of the comment, and Madison commented on their post, saying, “Yeah, trust me, if he was with her, he wouldn’t be sending me songs at midnight… last night. bless.” Yikes.

December 14, 2020

Screenshot via Instagram

The UncommonJames CEO was rumored to be dating Southern Charm star Austen Kroll after he and his co-star Craig Conover were seen on a night out together in Nashville with Kristin and Justin. After dinner, Justin went on his Instagram Live for now-infamous lip-sync performance of Taylor Swift’s ‘We Are Never Ever Getting Back Together’ and ‘Mean’ while Kristin danced on Austen’s shoulders. Justin was also seen in the video saying, “He doesn’t like you, Madison.”

December 15, 2020

In true Laguna Beach high school fashion, Kristin went on to shut down the speculation about her relationship with Austen, posting a clip of herself on her IG story rolling her eyes with the caption, “I didn’t realize I wasn’t allowed to have FRIENDS that are guys.”

Around this time Kristin’s ex-husband Jay was spotted visiting Austen’s ex-girlfriend Madison’s hometown. But nothing was confirmed. Yikes.

January 7, 2021

After almost a month of speculation, Madison responded to the rumors during Watch What Happens Live. She claimed she was “too busy having her own adventure” to notice what Kristin and Austen had been up to. And when asked about her “adventure” with Jay, she replied, “I’m not kissing and telling, so…” Sassy.

It’s important to note that by this time things seem to get really shady on both parts. And this is bringing awareness to Jay and Madison’s little romance. Meanwhile, Kristin was allegedly confirmed to be dating comedian Jeff Dye.

January 21, 2021

The Southern Charm finale finally aired, and it was explosive, to say the least. After the episode aired, Madison went on Instagram Live, drunk. In a lame attempt to mock Kristin and Austen’s Live, she decided to re-enact her own dance to “We Are Never Getting Back Together” by Taylor Swift. But things took a very ugly turn when she made jabs at Kristin’s parenting and the fact that Jay was relieved not to be with his kids…

“Don’t worry, my kid is at his dad’s. I think when that video was made, hers weren’t.” What this line insinuated was that Kristin had her kids that night and was drunk while they were in her care. A little bit of a mom shame, in most of the internet’s opinion.

January 22, 2021

Finally, the reconciliation post literally broke (and confused) the internet. Kristin and Jay both shared a friendly photo with the same cryptic caption, “The world is full of users. 10 years. Can’t break that.” At this point, no one knows what this means. But the momentum and speculation are building.

For those who were following the ongoing drama surrounding the former couple and the Southern Charm castmates’ former relationship, this post is basically screaming: “Don’t comment on my ex-wife’s parenting skills.” And that they stand together in unison. Clearly, they have each other’s backs.

But then Madison comments on Jay’s photo, “I told you it would all work out.” And Justin comments on Kristin’s photo another loving/supportive comment. So naturally, the internet sees both comments on each separate page and thinks, “They’re back together.”

Screenshot via Instagram

Since then, Madison was commenting on news outlets posts about her comment and replying to friends/viewers that she’ll share her side of the story.

January 24, 2020

But then Madison brought the receipts.

In response to being called a liar after clips of her sloppy live leaked, Madison posted screenshots of previous conversations with Jay that proved he pursued her first. It also confirmed that they did have a little something going on behind the scenes that no one knew about.

When Cutler alleged in one message that LeCroy had “insinuated” that something was going on between them, the reality star fired back.

It’s also important to note that it looks like she deleted some of her messages in the first screenshot she posted. Shady…

But in a quick turnaround, Justin clapped back on social media at the Southern Charm stars “thirsty” post. He also slammed the reality star for mentioning Kristin and Jay’s children in her Instagram Live. This was truly a #friendshipgoals moment.

He also fiercely defended his decision to speak out on the matter in a few pages’ comments. Clearly, he’s standing his ground and is not tolerating any negativity, and wants to clear his friends’ name. Especially for the sake of her children, who very well could be exposed to this nightmare.

Madison seemingly responded by posting another selfie with Jay and captioned it “too bad it didn’t work out.” Sadly, that’s the latest update we have, but this whole story is messy, to say the least.

It feels like a revenge plot where Madison is getting what she wants. And if you’re a true fan of Southern Charm, you would know how toxic Madison can be (the season finale that just aired proved it). This is very on brand for her as the typical crazy girl.

Do we know if Jay and Madison actually dated? I wouldn’t doubt it. But I don’t think Kristin and Austen dated — only because she’s been linked to someone else. Kristin and Austen only ever hung out in groups, despite him not being an angel.

I also think Madison looked at this stunt as a way to gain popularity over someone who is considered to be an OG reality Queen.

Let’s not forget who the original mean girl of reality TV is — it’s Kristin freaking Cavallari. And Madison wouldn’t be the reality star she is without Kristin. Why wouldn’t she want to take down the best of the best? She’s clearly trying to steal her title.

If anything, Madison made herself look crazy with her manipulation skills. Instead, Jay and Kristin seemed to have won because they’ve taken the high road and seemed united through the whole thing. They still look good even though Jay was a bit shady initially (and let’s remember, he’s no great prize either). However, I wouldn’t rule out that Kristin is strategically staying out of it knowing she’ll still have the last word — she knows how to control the drama even when it isn’t in her favor.

But if there’s one thing that has been clear in this wild shit show, it’s that: Madison is, in fact, the user. And this 15 minutes of fame she’s receiving because of it proves it.

Featured image via Kristin Cavallari on Instagram



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