It’s hard to imagine the pressure of being Jackson Holliday. When you're the son of an MLB legend like Matt Holliday and you get drafted first overall by the Baltimore Orioles, the spotlight doesn't just find you—it lives in your pocket. But honestly, if you follow the "Birdland" scene at all, you know that Jackson isn't the only one people are watching. Chloe Cox, now officially Chloe Holliday, has become a fixture in the narrative of the young phenom's rise to the big leagues.
They aren't just another flashy sports couple. In a world of "done-for-the-gram" relationships, these two feel surprisingly grounded. Maybe it’s the high school sweetheart energy. Maybe it’s the way they handled the whirlwind of 2024 and 2025. Whatever it is, people are obsessed.
The Story Behind Chloe Cox and Jackson Holliday
Let’s go back a bit. Before the million-dollar signing bonus and the Camden Yards cheers, Jackson and Chloe were just two kids in Oklahoma. They met at Stillwater High School. Think about that for a second. While Jackson was becoming the Gatorade National Player of the Year, Chloe was there. She wasn't some influencer who showed up after he made it; she was in the bleachers when he was still hitting against high school pitching.
They got engaged on December 28, 2022. It was a big deal on social media, but they kept the actual wedding pretty intimate for a couple of their stature. They officially tied the knot on January 6, 2024.
I remember seeing the photos—black and white, classic, very "old soul" vibes. Chloe wore a stunning side-slit gown, and Jackson actually looked comfortable in a suit, which is rare for a guy who spends 90% of his life in a baseball uniform.
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Life in the Public Eye
The transition from a high school star to the face of a franchise is brutal. Jackson’s debut in 2024 was... well, it was a rollercoaster. He struggled early on, got sent back down to Triple-A Norfolk, and had to find his swing again.
Through all of that, Chloe was the constant. You’d see her at the games, often with Jackson’s sister, Gracyn, or his mom, Leslee. That’s something you don't see with every "WAG" (Wives and Girlfriends). She’s deeply integrated into the Holliday family. It’s a support system that most 20-year-old athletes would kill for.
More Than Just a "Baseball Wife"
It’s easy to dismiss the partners of pro athletes as just being along for the ride. That’s not really the case here. Chloe has built her own following, mostly centered around fitness and lifestyle. She’s been pretty open about her routine, which honestly sounds exhausting.
- Pilates and Barre: She’s big on low-impact, high-burn workouts.
- The Sculpt Society: She’s mentioned using Megan Roup’s program for at-home sessions when they’re traveling.
- Nutrition and Balance: She talks a lot about not overdoing it and actually listening to your body.
She isn't trying to be a mega-celebrity. She’s just a girl living a very weird, high-stakes life and trying to stay healthy while doing it. It’s relatable, even if her "office" is a luxury suite at an MLB stadium.
The Anniversary and 2025 Milestones
Just recently, in January 2025, the couple celebrated their one-year anniversary. It’s a milestone that felt bigger than it was because of how much happened in that one year. Jackson went from a prospect to a regular starter, and they moved across the country to make Baltimore their home.
Chloe posted this really sweet note on Instagram about how she didn't think she could love him more than on their wedding day, but she does. It’s cheesy, yeah. But in the cynical world of professional sports, it’s also kind of refreshing. They also have a dog named Coconut who turned one recently too—the "Holliday pooch" basically has its own fan club at this point.
What Most People Get Wrong
People assume that because Jackson comes from money and fame, his relationship with Chloe must be easy. But think about the schedule. 162 games a year. Half of those are on the road. You’re living out of suitcases in hotels from April to October.
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For a young couple—both are barely into their 20s—that’s a massive strain. Most people their age are still figuring out what they want to major in. These two are managing a brand, a marriage, and a high-pressure career in the most public way possible.
The reason they work is because they seem to prioritize the "normal" stuff. You’ll see them at coffee shops in Baltimore or just hanging out at home with the dog. They don't seem to be chasing the "it" couple status; it just happened to them.
Handling the Critics
Jackson had a rough start in the majors. The internet can be a nasty place when a top prospect doesn't hit .300 in his first week. During those stretches, Chloe’s social media became a bit of a battleground of "fans" giving unsolicited advice.
The way she handled it? Mostly by ignoring it. She kept posting about fitness, family, and faith. It showed a level of maturity that you wouldn't necessarily expect from someone her age. She understands that her role isn't to be Jackson’s coach or his PR agent—she’s his wife.
Practical Takeaways from Their Journey
If you're looking at Chloe Cox and Jackson Holliday as a blueprint, there are a few things to actually learn from them.
- Build a Foundation Early: They didn't wait for the fame to decide they were a team.
- Keep Family Close: The fact that Chloe is best friends with Jackson’s siblings is a huge reason they stay grounded.
- Have Your Own Thing: Chloe’s focus on fitness gives her an identity outside of "Jackson Holliday’s wife."
If you're following the Orioles this season, keep an eye out for Chloe in the stands. She’s usually there, usually wearing some subtle O's gear, and usually being the calmest person in the room while Jackson steps into the box.
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Next Steps for Fans:
If you want to keep up with them, Chloe is active on Instagram (@chloehollidayyy), where she shares a mix of game-day fits and her workout routines. For the baseball side, keep an eye on Jackson's stats as he settles into his second full year in the majors. The pressure isn't going away, but with his support system, he’s probably going to be just fine.
Expert Insight: While many young athletes struggle with the distractions of the MLB lifestyle, the "Holliday Model"—pioneered by Matt and Leslee and continued by Jackson and Chloe—emphasizes early marriage and strong family ties as a way to maintain focus. This stability is often cited by scouts as a "plus tool" for Jackson's long-term development.