Devin Pearson wasn’t considering a career in baseball when he graduated from college three years ago. So being a member of the front office when the Red Sox won the World Series in 2018 wasn’t quite on his five-year plan.

After playing four years at the University of California Berkeley, where a slew of injuries held him back, Pearson was done with baseball. An outfielder, he had been drafted in the 30th round out of Carmel (Calif.) High School by the Toronto Blue Jays in 2012 and went on to play 185 games over four years at Cal. But a torn labrum, a broken hand, a broken hamate bone and then another labrum and rotator cuff injury put a halt to his playing days. 

“I always thought I would play (professionally),” Pearson said. “Got hurt and kind of needed to take a step away.”

Advertisement

Instead, after graduating he took a job in commercial real estate in Northern California. But he underestimated how much he’d miss baseball and its camaraderie, so he quit after three months and moved home. Pearson had stayed in touch with his coaches at Cal and made it known he was trying to get back into baseball. 

At the time, Pearson didn’t know Red Sox assistant director of amateur scouting Paul Toboni well, but their paths had crossed briefly. Toboni played at Cal, too, but graduated before Pearson’s freshman year. Toboni contacted Pearson and told him about a Red Sox internship program. It wasn’t glamorous, but it was a way into baseball. 

He applied, got the internship and moved across the country. Even though Pearson had played baseball his entire life and was good enough to play Division I ball in the Pac-12, one of the best college conferences in the country, the learning curve in the front office was steep.

“It was eye-opening for sure,” Pearson said. “I think every person who’s played baseball or college baseball player thinks they have a really good understanding of the game. But then you get into the front-office environment and it’s a totally different viewpoint of how everything works.”

The internship was focused on pro scouting, and Pearson worked directly with vice president of pro scouting Gus Quattlebaum and assistant director of pro scouting Harrison Slutsky, both of whom had been newly promoted to their roles.

“I did a lot of grunt work — obviously as an intern you kind of have to,” Pearson said. “But they also exposed me to all of the processes and how they worked and their thoughts. It was great being exposed from the bottom floor.”

Most of his time was spent in the office, located directly across the street from Fenway Park. Occasionally, he’d get a chance to head to Pawtucket to see Triple-A prospects in person, but most of his time was spent reading scouting reports, helping prioritize players to watch, as well as the typical intern duties like going on coffee runs and making copies. 

“A lot of times when young guys get into the game they seem to have a tendency to pretend they know more than they do,” Red Sox vice president of amateur scouting Mike Rikard said. “And that sometimes leads to exposure or mistakes or errors, and Devin has really never done that. He’s always been very comfortable understanding that he may not know certain things yet, but having that really good eagerness to learn.”

Advertisement

The long hours and desk work didn’t deter him. 

“I think I knew probably a couple months in that I wanted to do this (long term); just with the group that we have, it’s a really special work environment,” Pearson said. “Everyone is eager to teach you, and there’s a lot to learn.”

After that internship year in 2017, there was an opening on the amateur scouting side, where he’d be working directly with Toboni.

Pearson got the job and was promoted to an assistant in the amateur scouting department. Eight months later, he was standing on the field at Dodger Stadium holding the World Series trophy after the Red Sox won the title.

The players, of course, have the biggest impact on winning a championship, but the behind-the-scenes parts of an organization are integral to the whole process. The Red Sox traded three prospects last summer that netted major-league players who helped them win the World Series: Jalen Beeks for Nathan Eovaldi, Ty Buttrey for Ian Kinsler and Santiago Espinal for Steve Pearce. 

“If we trade players we drafted for big-league talent, that’s our job too,” Pearson said. “Whatever we can do to create value in the system is what we’re trying to do.”

In his full-time role on the amateur scouting side, Pearson’s job is heavily centered around the draft and helping rebuild the farm system. That’s a mandate for the entire amateur scouting department after the Red Sox system was depleted by trades for major league talent in the past few years. He spends large portions of the summer traveling across the country to various high school showcases and more locally to the Cape Cod League. Once the high school and college seasons start in February, Pearson spends more time in the office making sure the organization is prepared for the June draft with medical information and background profiles and scouting reports on the hundreds of players being tracked. 

At 25, Pearson is one of the youngest people in the draft room. And with his playing history at Cal, he brings a special perspective. 

“Having those experiences as a player certainly provides perspective coming in before you ever go through it,” Rikard said. “It’s certainly not a necessity, but I do think it adds another layer to someone that’s getting into the scouting world.”

Advertisement

The fact that Pearson is not much older than some of the players he’s scouting has led to some peculiar encounters, too. 

“It’s weird in some sense because there have been a couple kids I’ve scouted that I was their host on recruiting trips,” he said. “So getting to talk to them but also already knowing them has been cool, and then being there for them as much as I can without saying how interested we are or whatnot, if they have any questions. That’s been awesome to give those guys some advice as they move on with the draft process.” 

Though he’s only been on the job for two years, Pearson knows he’s found his passion. Whether that takes him more in a scouting or front-office direction remains to be seen.

“Devin is going to be able to do whatever he wants in the game,” Rikard said. “He’s got all those really rare and special attributes for a young guy you just don’t see that often. I know they’re going to carry him a long way.”

(Photo courtesy of the Boston Red Sox)