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  • Writer's pictureChelsea Roemer

For Better or Worse

Updated: Nov 17, 2023

The dark brown, somewhat damp dirt stood out against the faded grass that was still slightly frosted. Hanging low in the sky, gray clouds crowded together as winter temperatures and light rain were in the forecast, forcing Maine residents to keep their winter coats on just a bit longer. 

The date was April 6, 2023, marking Opening Day for the Boston Red Sox AA affiliate, the Portland Sea Dogs. Fans huddled closely in the stands to keep warm and cheer, while the team took the field for the first of 69 home games. 

I had always said I would never meet a more dedicated group of people at a ballpark than the season ticket holders. But my opinion of that was completely changed after observing a group of women who were also at Hadlock Field for each event, hot or cold, rain or shine. 

Growing up I attended many baseball games and followed the star players on social media. I saw pictures of them with their families and remember thinking how perfect their lives must be. They always lived in fancy houses, could afford private tutors for their children, and appeared to be wearing the latest fashion trends I saw in the magazines. 

Through the course of the season, my view of baseball families changed as it began to tug at my heart strings thinking about each woman in the stands, and how they potentially go days, weeks or even a few months without seeing their loved one.

To attain a better understanding of what it means to be cheering at every game, traveling to-and-from affiliates and everything in between, I spoke with Jessica Boerner, the wife of Red Sox pitcher Theo Denlinger. 

Unexpected Love Story

Jessica grew up in Menomonee Falls, Wisconsin, and competed for the St. Norbert women's basketball team, a Division III school outside of Green Bay, while earning a bachelor's degree in psychology. Theo is also a Wisconsin native, as he grew up in Cuba City, and then went on to play baseball at Bradley College in Peoria, Illinois. 

It was over the summer of 2020 when she and Theo crossed paths, as he was competing for a summer baseball team near her college town. After meeting at one of his games, the two went on their first date in July and eventually made their relationship official in September. 

“We thought this was going to be just a summer fling since we had both just gotten out of our big college relationships,” Boerner said. “But it instantly felt like we had already known each other for so long after we met.” 


Once the summer concluded, the two decided to go the long distance route as they returned to school, making trips to see each other throughout the next year. 

Roughly one year later, Theo was drafted in the seventh round by the Chicago White Sox and  began his career assigned to the Kannapolis Cannon Ballers. Jessica continued to visit him as much as she could before returning to St. Norbert for her senior season. 

After Theo was drafted, the two talked more seriously about getting engaged. 

“Both of us quickly realized that we never wanted to be without each other, and everything really just fell into place,” Boerner said. “I had always wanted to travel after graduating college since before I met Theo, and the baseball lifestyle at that point felt natural to us.” 

In December of 2021, Theo made it official and asked Jessica to spend the rest of her life with him. 

“We went on a Christmas trip to Door County, Wisconsin, where he wanted to take nice pictures and get dinner,” Boerner said. “He took me to a little spot on the water and got down on one knee, it could not have been more perfect.” 

The two have been legally married since May of 2022 due to the White Sox requiring a marriage license in order for spouses to be allowed to travel and live together in the provided housing. The couple plan to have their wedding this upcoming December. 

Unspoken Chaos 

After his first full season with the White Sox organization, Theo was traded to the Boston Red Sox in February of 2023. The trade occurred right before he and Jessica were set to drive to spring training in Arizona. 

“I remember my apple watch was blowing up because Theo was trying to call me non stop but I was at work and couldn't answer," Boerner said.“I found out when Theo’s brother texted a screen shot of the trade in our family group chat, and the rest of the day was spent frantically figuring out when his new report date was, and where we were going to live.” 

The two made their way to Fort Myers and were able to find a place to call home for the next couple of months, before heading up the east coast to Theo’s first assignment with the Sea Dogs. 

Making a quick pit stop before entering Maine, the couple adopted a great dane mastiff mixed puppy they named Cobalt to join them on their adventure, who has become a popular spectator at Hadlock Field. 

However, the chaos was not over just yet. After a short stint in Portland, Theo got the call up to Triple AAA at the end of May, meaning their family was going to need to relocate to Worcester, Massachusetts, for the time being. 

In late July, he was sent back to Portland, where the two would remain the rest of the season. 

“This is one of those things where you don’t really understand it unless you go through it yourself,” Boerner said. “Everyone assumes being married to a pro athlete means that everything is awesome and great all the time.” 

Luckily, the couple have very supportive family members that are willing to do what they can to help. 

“Our families are amazing and they do what they can to help pack and plan things,” Boerner said. “My parents even help me travel, either driving long distances with me to see Theo or helping me fly to see them when I am homesick.”

In Minor League Baseball, the teams compete in series that last from Tuesday through Sunday, and are only home every other week. This means that for the away series she is not able to travel to join Theo, Jessica remains in the city they temporarily call home. 

Boerner expressed how she keeps busy while her husband is on the road. 

“This was the first year I was with Theo for the entirety of the season and it did get lonely when he was away for a week,” Boerner said. “But I spent those days wedding planning, taking Cobalt around and hanging out with the other girlfriends and wives who were in town.” 

Meant to Be

Despite the occasions of uncertainty, there are little moments that make every part of this experience worth it. 

“It never gets old seeing him look for me in the stands when he enters the game,” Boerner said. “I love being there to be his support system in those moments, especially running to him after a game where he did really well.” 

Additionally, this journey has introduced Jessica to many other women who share the same experiences and can help one another get through the season.

“One of my favorite parts about this life is meeting his teammates and all the other wives and girlfriends,”Boerner said. “It’s nice to be surrounded by other women going through this and it's so cool that we have friends from all over the country.” 


After speaking with Jessica, I am convinced she and the other women put on their invisible red capes before heading to the ballpark after keeping everything organized on the home front while their husbands are at work for about 8-10 hours a day. 

“Never forget how important you are to your man,” Boerner said. “You will feel lonely and doubt your purpose at times, but remember that you are the light at the end of his long days and weeks.” 

I know the Denlinger family is just one example of what a relationship in the baseball industry looks like, and that everyone’s experience is entirely unique. 

But none of it seems easy as I have heard of wives who must find temporary work just to make a little extra cash to help with finances, choose to put their careers aside to travel with their husband, or sacrifice time with their husbands to stay home and work to care for their family. 

For those in professional baseball needing resources for their families such as housing recommendations, check out Our Baseball Life:

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