It all apparently began with Madison mentioning Cavallari's parenting choices during an Instagram Live last week -- after alluding to a possible relationship between herself and Cutler on "Watch What Happens Live" earlier this month.
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On Friday, Cavallari and Cutler then shared a photo of the two of them together with the caption, "The world is full of users. 10 years. Can't break that," a comment many believed was aimed at LeCroy. Madison jumped into Cutler's comments to write, "I told you it would all workout," before writing on another page, "Can't wait to clear this up."
She also took to her own Instagram Story to add, "It looks to me like I'm going to have to drop some receipts. Hate to do that... but."
On Saturday, Cavallari's BFF Justin Anderson also got in on the drama by posting a shady TikTok and confirming it was 100% in reference to LeCroy in the comments.
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"She's trying to fool everyone. She's obviously truing to play THAT reality tv part for attention. never works. truth always comes out," he responded to some of his followers.
"She knows nothing happened with [Southern Charm's Austen Kroll] and Kristin but she thought it was a cheap way to gain attention," he continued. "Never works in the long run. If she wants to do the fake tv drama thing she needs to keep it where it belongs."
He added, "if everyone stops saying Madison's name she'll stop making stuff up for attention. She's created all of this nonsense. It's cheap. She's drama."
On Sunday, LeCroy finally made good on her promise to "drop some receipts" by sharing text messages she claimed were between her and Cutler.
In the first conversation she shared, the person she claimed was Cutler allegedly said he was coming to Charleston, South Carolina to "hang out" with LeCroy. "Do you want to hang out next weekend?" the text asked, before adding, "Ok. Don't stress about it. I bought the flight yesterday because it was the last direct one. If it doesn't work out I can change it to some other time." He then allegedly added, "Perfect."
The lack of responses from LeCroy between those three texts had many wondering whether she deleted her replies.
The second alleged conversation began with LeCroy asking, "Why would you do that?" The reply: "It was insinuated and my name was also brought into it which I don't appreciate."
"Jay I've done nothing but respect you and your privacy," she responded. "I respect you and I respect your family and I would never say anything to jeopardize you and your family."
"Didn't seem like that was the case," the reply read. "Maybe it was accidental. I don't know. No one wants this mess. I appreciate you saying that. I think we can all respect each other and move forward. At the very least."
LeCroy went on to say she was "disgusted" by the entire situation and said he was the one who first reached out to her. "Your intentions may have not been pure but that may be you projecting. I've never said anything about Kristin nor would I," she continued.
"I came into this honestly with good intentions. I want no part of being involved in a payback or drama," she added.
The text ended with her writing, "If you weren't interested in something real you shouldn't have [blank] with me." The last comment was covered up with a superimposed comment reading, "I kept my mouth shut until I get called a liar."
LeCroy then shared a photo of her apparently with Cutler, adding, "Too bad it didn't work out."
So far, Cutler hasn't responded. TooFab has reached out to his rep for comment.