Jay Cutler Finds New Love With Samantha Robertson After Splitting From His Wife, Kristin Cavallari
October 28, 2026
Last updated by Sangita Budhathoki on October 28, 2026
Prior to their 2026 divorce, Jay Cutler shared seven years of marriage with Kristin Cavallari, resulting in three children: daughter Saylor and sons Camden and Jaxon.
Key Takeaways
- After a three-year relationship, Jay and Kristin tied the knot on June 7, 2013, building a family together.
- Their romantic history also includes connections with TV personality Madison LeCroy and singer Jana Kramer, though Jay ultimately found lasting companionship with Samantha Robertson.
Former NFL star Jay Cutler, known for his 12-year career with the Chicago Bears and numerous records, now faces public attention for legal issues unrelated to sports. The athlete, honored among the 100 best Bears in 2019, was recently detained for DUI and gun possession while intoxicated.
Authorities arrested Cutler following a minor traffic collision in Franklin, where he allegedly struck another vehicle around 5 PM. Kristin Cavallari, in a podcast interview, expressed support for Jay while hoping he receives necessary help.
Post-Divorce Life: Jay Cutler Thrives With Samantha Robertson
Following their April 2026 divorce declaration—after years of estrangement and financial resolution—the couple’s current bond remains strong. Their story mirrors resilience, having navigated personal and public challenges since their initial split.
Samantha Robertson, previously married to Trace Ayala and mother to Sophia and River, met Jay during mutual divorce proceedings. The pair, once family friends, grew closer amid shared life transitions.
Robertson and Cutler’s international adventures highlight their partnership, with Samantha often sharing glimpses of their travels. Meanwhile, Cutler continues community involvement through Vanderbilt’s Best Buddies program, supporting youth development.
Interesting Facts
- Cavallari briefly dated TikTok creator Mark Estes (Feb-Sept 2026), sparking media interest due to their age gap.
- Cutler balances sports legacy with creative pursuits, including music performances alongside his writing career.
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