If you’ve been following the whirlwind of headlines surrounding former NFL quarterback Jay Cutler lately, you probably noticed a shift in the narrative. For years, the story was strictly about the fallout from his high-profile divorce. Then came the rumors. Then came the Instagram posts from Montana and France.
Now, in early 2026, the picture is much clearer. Jay Cutler and Samantha Robertson aren't just a "rumored couple" anymore—they are very much the real deal, and they've been navigating the complexities of a modern, blended celebrity life for well over two years.
The Timeline Nobody Talks About
Most people think this relationship popped out of nowhere. Honestly, it didn't. While the world was busy dissecting every podcast episode featuring his ex-wife, Kristin Cavallari, Cutler was quietly moving on.
The timeline basically kicked off in the summer of 2023. They weren't exactly hiding, but they weren't shouting it from the rooftops either. They were spotted at a wedding in France—very chic, very low-key. By September 2023, Samantha made it "Instagram official" with those now-famous sunset photos in Montana.
"Sunsets in Montana never disappoint," she wrote. Jay’s response? "When are we going back?"
It was a vibe. But it wasn't just a vacation romance.
The Engagement That Caught Everyone Off Guard
Fast forward to late 2024. The couple showed up at the Yellowstone Season 5B premiere in New York City. Jay looked like his typical stoic self in a gray blazer, but all eyes were on Samantha's left hand.
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That "massive diamond sparkler" wasn't just an accessory.
Multiple sources confirmed the engagement shortly after. It was a big deal, mostly because it signaled that Cutler was finally ready to commit again after the 2020 split that dominated the tabloids for years. By January 2026, the focus has shifted from "are they or aren't they" to how they’re making their new life work in Nashville.
Who is Samantha Robertson, Really?
There’s been a lot of weird misinformation floating around about Samantha. Some sites confuse her with a PhD student at Berkeley or a social worker in New Hampshire. Let’s clear that up.
Samantha Robertson is an aspiring actress and designer. More importantly to her daily life, she’s a mom. She has two daughters, Sophia and River, from her previous marriage to Trace Ayala.
If that name sounds familiar, it’s because Trace is Justin Timberlake’s longtime best friend and business partner (they started William Rast together). Samantha has deep ties to that creative, Tennessee-meets-Hollywood circle. She isn't just a "football player's girlfriend"—she has her own history and a very established life in the same Nashville circles where Jay resides.
The Blended Family Dynamic
This is where it gets interesting. Between the two of them, they have five kids. Jay has three with Cavallari (Camden, Jaxon, and Saylor), and Samantha has her two girls.
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Blending a family of that size is no joke.
Sources close to the couple have mentioned that the kids have all met and actually get along quite well. That’s a huge win in the world of messy celebrity divorces. Interestingly, Kristin Cavallari actually spoke about this on her Honestly Cavallari tour. She mentioned that she actually knew Samantha before the divorce.
"I knew her before, so I think that helped because I could sort of envision their dynamic," Cavallari said. It’s a surprisingly mature take on a situation that could have been incredibly awkward.
Addressing the DUI Incident
We have to talk about the elephant in the room. In October 2024, Jay Cutler was arrested in Franklin, Tennessee, following a rear-end collision. He faced charges including a DUI and illegal possession of a gun.
It was a messy moment.
Many wondered if the relationship with Samantha would buckle under the pressure of the legal drama and the subsequent media frenzy. Instead, she was right by his side at that Yellowstone premiere just two weeks later.
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She hasn't made a public statement about the arrest. She doesn't really have to. In the world of high-stakes relationships, sometimes staying silent and showing up is the loudest statement you can make. It showed a level of loyalty that many didn't expect.
What Really Matters Now
As we move through 2026, the "Jay and Samantha" story has transitioned from a tabloid curiosity into a stable partnership. They’ve managed to keep most of their private life actually private, which is a feat when you’re a retired NFL star and a socialite in a town like Nashville.
The couple frequently shares glimpses of their life on social media—hunting trips, ranch life, and quiet moments that feel a lot more grounded than the "reality TV" lifestyle Cutler was once part of.
Here is what you should actually take away from the Jay Cutler and Samantha Robertson story:
- Privacy is a choice: Despite their fame, they’ve managed to control the narrative by only sharing what they want, when they want.
- Blended families require work: With five kids between them, the focus remains on the children’s stability rather than public drama.
- Resilience sells: The way they navigated Jay's legal issues in late 2024 proved they are a united front.
- History helps: The fact that the "exes" are largely on board (or at least cordial) makes the transition much smoother for everyone involved.
If you’re looking for the next steps in following their journey, keep an eye on Samantha’s design projects. She’s been hinting at new ventures that lean into the Nashville aesthetic. As for Jay, he seems perfectly content trading the football field for the farm, as long as he’s got the right person by his side.