Joshua Goldman
Joshua Goldman
min read · September 2, 2025 · Entertainment

Kristin Cavallari Unveils Her 'Troublemaker' Past: From Shoplifting to Run-ins with the Law

Kristin Cavallari candidly talked about her rebellious side while growing up as she drank, shoplifted, and even had multiple run-ins with the law

EXCLUSIVE!

Reality TV Star Kristin Cavallari Spills Juicy Details About Her Wild and Rebellious Past!

Kristin Cavallari, the 38-year-old reality TV star, is no stranger to controversy, but in a shocking new episode of her podcast "Let's Be Honest", she dished out juicy details about her wild and rebellious past that left listeners speechless!

Kristin revealed on the latest episode of her Let's Be Honest Podcast - titled My Career In Being The World's Biggest Troublemaker - that her mean streak began in fourth grade (she is pictured with her late brother Michael)

As a teenager growing up in the affluent coastal enclave of Laguna Beach, California, Kristin revealed that she was a bit of a troublemaker. She confessed to having a mean streak that began in fourth grade when she wrote the "f-word" in her diary, which was confiscated by her teacher and sparked a heated argument.

However, it wasn't until eighth grade that Kristin's wild behavior truly escalated. She confessed to pulling off some outrageous stunts, including faking illness and calling out of school, taking trains without adult supervision, drinking booze at school, and even piercing her bellybutton with only a safety pin!

But the icing on the cake came when Kristin revealed that she was caught shoplifting in high school. In a candid conversation, she admitted to putting multiple bras, T-Shirts, and shorts under her pants, trying to see how much she could get away with.

She also recalled when she and former boyfriend Stephen Colletti  (pictured together around that time) had been pulled over while having an argument and police had escorted her back to her father's house as she wasn't even 18 at the time

The drama didn't end there! Kristin recalled being pulled over with her then-boyfriend Stephen Colletti after they got into an argument and the police escorted her back to her father's house because she wasn't even 18 at the time!

This comes as a surprise to fans, especially considering her ex-husband Jay Cutler's recent claims that she "borderline slandered" him in her podcast by stating she didn't receive any money from their divorce.

JAY CUTLER FIRES BACK!

In an explosive interview on the Take It Outside podcast, Jay Cutler blasted Kristin for her comments, saying: "Let's think about this logically. 'Not a penny,' OK. Married for seven years or so, three kids... You can go and see how much I made in the NFL. It's online. You can see the contract from year to year and the total amount at the end of 12 years..."

Jay went on to say that there was no way a judge would have signed an agreement stating he kept every single dollar he made throughout their marriage, contradicting Kristin's claims.

UNCOMMON JAMES: THE REAL STORY BEHIND KRISTIN'S LIFESTYLE BRAND

In a bombshell revelation, Kristin dropped some tea about her successful lifestyle brand Uncommon James. She claimed that she has never taken any outside funding and that she didn't get any money from their divorce, sparking rumors of Jay's involvement in the brand.

However, sources close to the matter reveal that Uncommon James was indeed a marital asset, funded during their marriage. This raises questions about Kristin's honesty regarding her financial situation with Jay.

JAY'S CONTROVERSY: THE WILD ANIMAL KILLING SCANDAL

But that's not all! Jay Cutler recently sparked outrage on social media after sharing a photo of himself posing alongside a wild Sable Antelope he shot dead during a hunting trip in South Africa. The comments were filled with angry responses, with some users calling him "cruel" and "impressive" at the same time!

As Kristin's past continues to make headlines, fans can't help but wonder what other juicy secrets she might spill on her podcast. Will she dish out more tea about her divorce or Jay Cutler's latest controversy?

Only time will tell, but one thing is for sure: Kristin Cavallari's wild and rebellious past is only getting wilder!