Calvin Bickerstaff's Unique Path to Professional Baseball Has Him Ready to Succeed With Red Sox [Exclusive]

Not everyone has the same path to professional baseball. While some will end up drafted, others will find out in the wildest of ways that their dream gets to continue. For Boston Red Sox prospect Calvin Bickerstaff, calling his draft experience unique would be an understatement.

“I talked to a few teams throughout my senior year and nothing too crazy [came of it], so I was unsure going into the [draft], but had a feeling. I had a workout leading up to it and the day before the first day of the draft my college coach called me and said ‘We’re going to send you out to the Cape [Cape Cod] League to finish out the summer.' So, I was like, when do I need to be there and was told to be there in two days,” Bickerstaff explained.

During the hectic travels, he admitted that communication was often bare when it came to the draft. The trip to play in the Cape Cod League was one nobody never would have imagined playing out how it did. “Drove out during the first day [of the draft] and finished the drive on the second day. On the third day my team had an off day so my dad who drove out with me, we were going to watch another Kent State player pitch.

“I had never talked to the Boston Red Sox. I didn’t talk to them in high school, didn’t talk to them junior year or senior year. And we’re on the way [to the game] and my agent calls and says the Red Sox might take you. There’s one guy ahead of you, if they don’t take him, they’re going to take you. They ended up taking him and he [the agent] called me back and said they still want to take you.”

While it was a 10-hour drive to get to Cape Cod and Bickerstaff never got to pitch even an inning, the drive back was easy. Even going as far as to describe his feelings as “being on cloud nine” during the ride back home. The rest for Bickerstaff was history. After pitching three seasons for Kent State that saw him appear in 56 games and tossing 122 2/3 innings, the right-hander was a professional athlete. Signing as an undrafted free agent, he would eventually make his professional debut for the then Salem Red Sox in 2024.

Tossing 6 1/3 innings, the right-hander struck out seven batters. It had been a long journey, one that had helped to shape him into the pitcher he is today. He continued to grow, after his senior year in high school was cut short due to Covid-19; the former high school senior that was thrown off of baseball fields during the spring and summer of 2020 would go on to turn himself into a prospect after his college career.

“The main thing was trying to figure out a way to stay in ready. We couldn’t use baseball fields in our community. I got kicked off of two different fields because I couldn’t even access my high school field, it was a college field for Franciscan University of Steubenville,” Bickerstaff reminisced about the end of his high school career. “They had the whole facility locked, but I would hop the fence of local high schools with a catcher. Next thing you know somebody was there to kick me out.”

Fortunately, the right-hander had already committed to Kent State during his sophomore season and did not have to worry about the pandemic taking away his chance to pitch in college. But since signing with Boston following the 2024 draft, Bickerstaff quickly learned there was a difference between the college level and professional baseball.

“It was everything I expected. It was great. I finished the month in Salem, Single-A, it was great. The days in pro ball were a bit different. It’s like practice every day and if you’re available, then you’re playing. It was a little different but awesome. I’m lifting, running, eating well, and then throwing.”

Since signing with the Red Sox, Bickerstaff has spent time at four different levels, pitching in the Florida Complex League briefly in 2025 and making it all the way to Portland for a brief stay in 2026. Most of his time in the system has been spent with High-A Greenville. Overall, he’s appeared in 55 games and tossed 121 innings with a 4.31 ERA and 110 strikeouts. For someone who has bounced between the bullpen and rotation since high school, he admits that there is a difference in mindset if he knows he’s going to start or relieve, but he revels in being a flexible pitcher.

“The biggest difficulty was going from high school as a starter to the bullpen in college. I would take my time, as much as I needed—15 minutes throwing a pregame bullpen, looking back I was throwing way more than I should have. That first year in the bullpen, I’d go in the first or second inning due to trouble and it’s like I got to figure this out because I don’t feel prepared. But I eventually figured it out."

The right-hander continued to explain how his mindset also shifted depending on his role. If he were starting, Bickerstaff knew he needed to pace himself, planning not just for the current inning, but for what laid ahead for the rest of his outing. Since moving back to the bullpen after getting drafted, he’s viewed throwing each pitch as if “it’s the ninth inning”.

In 2026, he’s appeared in 28 games so far, making one appearance for Salem, one for Portland, and 26 for Greenville. He’s given the organization 68 2/3 innings with a 4.33 ERA, striking out 53 and walking 22. The next step for Bickerstaff is to make it back to Portland as a permanent promotion, though even that is just a stepping stone on his unlikely journey all the way to the big leagues.

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