Jay Cutler & Kristin Cavallari: 5 Shocking New Details About Their Co-Parenting, Engagements, And Bitter Money Feud

As of December 2025, the post-divorce lives of former NFL star Jay Cutler and reality TV icon Kristin Cavallari are more dramatic and newsworthy than their six-year marriage ever was. The former couple, who officially finalized their divorce in 2022, have both moved on with new, high-profile relationships, but the drama over their financial settlement and the delicate balance of co-parenting their three children continues to make headlines. This is the definitive, up-to-the-minute look at where they stand now. The journey from their initial whirlwind romance to their contentious split has been a decade-long saga that captivated fans of the Chicago Bears, *Laguna Beach*, and *Very Cavallari*. Despite the public scrutiny, both are focused on their respective business empires and maintaining a stable environment for their family, even as new partners enter the picture.

Jay Cutler & Kristin Cavallari: Complete Family and Career Biography

The relationship between the famously private NFL quarterback and the famously public reality star was always a study in contrasts. They began dating in 2010, got engaged in April 2011, briefly called off the engagement a few months later, but quickly reconciled and were married in 2013. Their split was announced in April 2020, and the divorce was finalized in 2022.

Kristin Cavallari's Profile

• Born: January 5, 1987 (Age 38 as of late 2025)
• Career: Television Personality, Fashion Designer, Author, Businesswoman.
• Notable Work: *Laguna Beach: The Real Orange County* (2004–2005), *The Hills* (2009–2010), Founder and CEO of the jewelry and lifestyle brand Uncommon James, star of the E! reality show *Very Cavallari* (2018–2020), author of *Balancing in Heels* (2016).
• Current Status: Dating a new, unnamed retired athlete as of late 2025.

Jay Cutler's Profile

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• Born: April 29, 1983 (Age 42 as of late 2025)
• Career: Former Professional American Football Quarterback.
• Notable Work: Played for the Denver Broncos (2006–2008), Chicago Bears (2009–2016), and Miami Dolphins (2017). Known for his strong arm and stoic demeanor.
• Current Status: Reportedly engaged to fiancée Samantha Robertson as of late 2025.

Children (Co-Parented)

• Camden Jack Cutler: Born August 2012 (Age 13)
• Jaxon Wyatt Cutler: Born May 2014 (Age 11)
• Saylor James Cutler: Born November 2015 (Age 9)

The Co-Parenting Dynamic: Primary Custody and Recent Changes

The most important entity in their post-divorce lives is their three children: Camden, Jaxon, and Saylor. Despite the public acrimony between the parents, both Jay and Kristin have consistently stated that they prioritize a healthy co-parenting environment.

In recent updates, Kristin Cavallari has retained primary physical custody of their children. She has been candid on her podcast, discussing the complexities of raising three kids while navigating a high-profile split. The reality star recently revealed a change in their custody agreement, which she has described as "really good" for the family's stability.

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The former couple's ability to maintain a functional co-parenting relationship is a testament to their commitment to their kids. Jay Cutler himself has publicly confirmed that they "have done a good job" of making the custody arrangement work. Their focus remains on their children's well-being, even as they introduce new partners into their lives.

New Engagements and Retired Athletes: The 2025 Dating Scene

The most recent and attention-grabbing news revolves around both Jay and Kristin finding love again, two years after their divorce was finalized.

Jay Cutler’s Engagement to Samantha Robertson

In a major update in late 2025, reports surfaced that Jay Cutler is engaged to his girlfriend, Samantha Robertson. The former Chicago Bears quarterback and Robertson went Instagram official in September 2023, and the news of their engagement solidifies his move forward. Robertson, who is a mother herself, has seemingly meshed well with Cutler's life, signaling a serious step away from his past with Cavallari.

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Kristin Cavallari’s New Retired Athlete Boyfriend

Kristin Cavallari has also confirmed she is dating someone new following her split from Mark Estes in October 2024. The new man, whose identity she has kept private because the romance is "really new," is described as a 40-year-old retired athlete and a father with children from a previous relationship. This marks a return to dating athletes for the Uncommon James founder, though she has not disclosed his name, sparking significant curiosity among fans and the media.

The Bitter Financial Feud: The "Not a Penny" Controversy

While the co-parenting is reportedly smooth, the financial aspect of the divorce continues to be a point of contention and public drama. The divorce was settled out of court in 2022, but the details of the financial settlement have been messy and disputed.

Kristin Cavallari famously claimed in a public statement that she "didn't get a penny" from Jay Cutler in the divorce settlement. This claim ignited a firestorm, especially since the couple had been married for six years and had three children together. However, Jay Cutler immediately pushed back against this narrative, calling her claim "completely false."

Cutler has maintained that he has the 67-page court document to prove his side, suggesting his ex-wife's statement was "reckless" and misleading. The dispute highlights the ongoing tension over money, particularly concerning the assets accumulated during their marriage. Cavallari has also been adamant that her successful brand, Uncommon James, was 100% her own and was not funded by Cutler. This lingering drama proves that while they are legally separated, the financial ties and public disagreements are far from over.