How a heartfelt promise and those closest to him fueled Caleb Freeman's return to the Cape League

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When Caleb Freeman takes the mound, he's playing for more than himself.

From the earliest stages of his life, he was instilled with key values that he has carried with him throughout his life, many of which he picked up from his resilient grandmother, Barbra Labosco.

"I get my compassion, love, and care for people from her. She was a single mother raising my dad — staying strong through that takes a lot," Freeman said.

Just three months after Caleb's birth, Labosco moved to South Carolina just a neighborhood away from the Freemans, which sparked an inseparable bond between her and her grandson.

"I'd go over there constantly, breakfast, lunch, dinner, whenever," Freeman recalls.

Caleb's father, Jason, a former pro tennis player, instantly noticed the positive impact his mother began to have on his son's life and calls her constant presence a "crucial role in his upbringing."

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A young Caleb with his dad and grandmother

Earlier this year, the close-knit relationship was met with a profound loss. Barbra's health began to decline in December, a heartbreaking reality Caleb and his family had to face.

"We slowly began to see her deteriorate right in front of our eyes. That was more stressful than anything I think, it was like, when is the day going to come," Caleb said.

Sadly, on March 10, Barbra Labosco passed away, leaving behind a legacy of love, compassion and strength — values that Caleb continues to carry near to his heart. Whenever he steps on the mound, he's actively carrying on his grandmother's legacy.

"She helped give me a why and it's pretty simple. Spread love, positivity and joy to people around me, all while putting a smile on their faces," Caleb said. "I know I can't impact everybody, but I know from my experiences this past year that simply saying hello or asking someone how they're doing can make a big difference. My goal is to spread positivity to everyone around me."

Caleb has only fond memories of his grandmother, whether it was seeing her in the stands at every one of his games, going over to her house for cookies, or receiving a birthday card signed "Love always," but it's the memory of their final moments and the promise he made to his late grandmother that he holds closest.

Amid a subpar outing at North Greenville in the spring following a short stint with the Brewster Whitecaps in the summer of 2023, Caleb Freeman promised his grandmother that it wouldn't be long before he was back on the Cape.

"My last words to her were: I'm going to get back to the Cape, and that's a promise," Caleb said.

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Caleb and his grandmother

With his arrival back to the Cape Cod Baseball League, once again being a late-season addition, this time to the Firebirds roster, Caleb followed through on his promise to his grandmother and made it back to the biggest stage in college baseball.

"I got chills when I got the call. It was so surreal, all I could think about was, my promise is fulfilled now," Caleb said.

"I had a really bad first outing with all the emotion and everything coming together, but I truly enjoyed every second of my time in Orleans."

Even though Caleb only had two short stints in the Cape League, the Freemans were no strangers to the Cape. Like many, they have called the Cape their summer home for as long as they can remember.

Jason Freeman, who summered in Truro, brought his son on a SCORE International mission trip to the Dominican Republic when Caleb was in the sixth grade, despite his less religious beliefs at the time.

Little did Jason know, that simple trip would change his son's life, and provide him with another lifelong mentor.

Ron Polk, known as "The Father of Southeastern Conference Baseball," was on a 12-tour journey through the Dominican Republic with SCORE International and spoke at a banquet that happened to be at the time of the Freemans' trip. After coach Polk's speech, he and Caleb kept in touch and formed a bond that Freeman still cherishes today.

"He took me under his wing for absolutely no reason, I never played for him and had just met him, and now he's one of my favorites in my phone," Caleb said.

"We talk about once or twice a month, and he always ends the call by telling me he loves me. I'll always value the relationship we've built."

Polk, a legend of the sport, has assisted Caleb along the way of his baseball career all while watching him transform into an incredible person.

"He has a batting cage in his backyard, so I'd throw some baseballs to him and lend some instruction," Polk said.

"I've also seen him grow as a person and he's become a great young man. But I don't take away what his mom and dad have done, they've done a great job raising him."

Caleb's father displays the same gratitude to Polk, emphasizing that since their trip to the Dominican, he's held an important role in his son's life.

"He's been an unbelievable person in Caleb's life," Jason said. "He checks in, always makes sure to call him, and has more or less been a godfather."

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Caleb Freeman with Coach Ron Polk by his side

In 2016, Polk had a Cape League stint of his own, as an assistant with the Hyannis Harbor Hawks, and invited a 12-year-old Caleb Freeman to speak in front of the team in the clubhouse.

"It's funny, he was only 12 years old and hadn't hit puberty yet, so he still had that squeaky voice," a laughing Polk said. "When he talked to the team I think they could barely hear him."

On that Harbor Hawks team was Colby Bortles, now an assistant coach and the recruiting coordinator at Jacksonville University.

Caleb's time at North Greenville didn't go as expected, which sparked a search for another university for him to represent on the mound. Not long after entering the transfer portal, Bortles, who Caleb's prepubescent self spoke in front of eight long years ago in Hyannis, gave him the call to offer him a scholarship to play at Jacksonville.

Full-circle moments like those, plus his son's determination, lead Jason Freeman to believe one day he'll be seeing his son in the show.

"Do I believe he's going to outwork everyone and play professionally somewhere, however it takes? Yeah, I do," Jason said. "But in the same breath, some of these things that have meticulously played out just tell me it's meant to be."

The hard-working and attentive father lives by two sentiments that he has preached to his children for as long as he can remember, and that have been drilled into Caleb's head by an inner circle that only has his benefit on their mind.

"I believe that it's about two things. How do you treat people? Not just if you speak to people and say hi, but how do you truly treat people? How do you treat the poorest person or someone who's meaningless to you? And No. 2, how's your effort? Did you give it your all?" Jason said.

"I think those are two things that come from Polk, and I've preached it back to him forever, but coach Polk really helped implement those values within him."

Throughout all the heartache, Caleb Freeman has persevered and continued to find ways to bounce back. He hopes his story can serve as a testimony that brighter days are on the horizon for those who may be going through similar ups and downs.

He has a simple message for those who still find the strength to put a smile on every day, even though all might not be put together on the inside.

"To anyone out there struggling in a dark place, just know that perseverance will lead you to the inevitable light at the end of the tunnel."

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Caleb Freeman (middle) during the national anthem of the Firebirds 2024 wildcard game|Art or Photo Credit: Sophia Soropoulos