Red Sox putting their faith in new scouting boss Devin Pearson as draft nears

May 30, 2024

Sunday marks the end of the first half for every team in baseball.

But as most within the sport take a much-needed break, MLB scouting directors and their amateur scouting staffs will be working around the clock in the midst of their most frenetic week of the year. The First Year Player Draft commences at 7 p.m. Sunday and runs for 20 rounds through Tuesday evening as organizations seek their next big homegrown stars and reshape their farm systems.

This season, the Red Sox have a new face in charge of their draft: Devin Pearson.

Pearson joined the Red Sox as a pro scouting intern in 2017 and quickly rose to an amateur scouting assistant before being named assistant director of amateur scouting two years later under then-scouting director Paul Toboni. Toboni led the Red Sox drafts from 2020 through 2022 as the franchise signed some of the best current players in their farm system, from Marcelo Mayer and Nick Yorke to Roman Anthony and Blaze Jordan.

This offseason, the Red Sox announced some restructuring within the front office. Toboni was elevated to vice president of amateur scouting and player development, a role that oversees how drafted players are developed in the Red Sox system. That paved the way for the 29-year-old Pearson to step into the top role as scouting director.

The draft has always been an important piece of building and sustaining the organization, but under chief baseball officer Chaim Bloom, it has arguably been a primary focus, making it all the more important that Pearson continue the success of the last few years.

Those that have worked closely with Pearson since he arrived in Boston in 2017, and particularly since he took over this offseason, feel the organization hasn’t missed a step under his leadership. His first draft will obviously be the biggest test, but his work to this point has left many impressed.

“Quite honestly you talk about the transition and how things have changed and they really haven’t,” said vice president of scouting Mike Rikard, who was Red Sox scouting director from 2015-19, but now holds a senior position scouting amateur, professional, and international talent for the organization. “Paul has kind of set this standard and Devin learned so much from him being his right-hand man, it’s really been a seamless transition to what we have going.”

“It takes having a really good way about you,” Bloom said of Pearson, “and it takes the right mix of confidence and humility. Devin has that. He’s not afraid to have an opinion, but he really respects people around him.”

While the importance of draft week itself is obvious, it’s really the months — and in many cases years — of preparation that go into the scouting process that matters most. Refining the draft board and ordering players not only by the Red Sox’s desire to sign them and the players’ ability to thrive within the Red Sox system, but also by the likelihood the player will still be available when the Red Sox have their pick, all play into the process.

This year the Red Sox pick at No. 14 in the first round, No. 50 in the second, No. 83 in the third and No. 115 in the fourth. They have two compensation picks after Round 4 at No. 132 and No. 133 for qualifying offer free agents Xander Bogaerts and Nathan Eovaldi signing elsewhere. (Those picks would have been after the second round if the Red Sox had been under the luxury tax threshold last season.)

No matter how prepared the amateur scouting group is, there’s always room for unpredictable outcomes. In 2021, the Red Sox were floored that they were able to land Mayer with pick No. 4 as he was expected to go within the first couple picks; Mayer remains one of the top prospects in all of baseball. In 2020, they surprised much of the baseball world by selecting Nick Yorke in the first round; Yorke has largely justified their faith in him. Preparation is key.

Pearson is leading the charge as decisions are made with Toboni and the Red Sox front office group, but there are dozens of others intimately involved in the entire process, none more important than the 30 amateur scouts and cross-checkers spread across the country. Amateur scouting special assistant Justin Horowitz, coordinator Jake Bruml and assistant Mark Sluys all support Pearson in research and in synthesizing the draft profiles from scouts. Assistant director of analytics Dan Meyer and the analytics group work in tandem with the scouting department to make the reports on each draft prospect as robust as possible.

Information and reports from scouts arrive daily throughout the year, but sit-down meetings to narrow the list of players happen a few times a month at the start of the year before progressing to once a week as the draft draws closer. Eventually, the meetings turn daily as variables in the process change and the draft looms.

“We’re lucky we have a really, really good scouting group that I trust their opinions more than my own in a lot of cases,” Pearson said. “They’re the leverage evaluators who have been doing this a long time. The scouting director role, it isn’t how it’s been in the past where maybe it’s your best evaluator and that’s what you’re going off of; we’re lucky to have a good group of evaluators.”

The trust goes both ways. While a younger scouting director taking over the top job might worry some, Pearson — who played collegiately at the University of California-Berkeley and effectively joined the Red Sox front office right out of college — has found a delicate balance of pushing his colleagues for more while also letting their expertise guide decisions.

Pearson when playing at Cal in 2015. (AP Photo / Juan DeLeon)

“I think a lot of it circles back to how he’s garnered everyone’s trust quickly,” Toboni said. “That’s unsurprising and he does it in a way that’s very natural so everyone that works in the department feels how much he cares for them and the Red Sox, and makes it easy for him to lead.”

It wasn’t long ago that there was a division between scouts on the ground and the analytics department in baseball. In some cases that may still be true, but the Red Sox feel they’ve found a sweet spot of relying heavily on both. The draft process now involves a crucial blend of on-site evaluations and relationship building between seasoned scouts and draft-eligible players in addition to analytical tools that enhance the whole process.

“What we’re talking about is similar to a radar gun,” Pearson said. “When the radar gun came out and scouts were able to know exactly what the velocity was on the gun, that helped them do their job better. There are analytical tools nowadays that, by scouts knowing what that stuff means, can do their job better. We’re lucky our group has been really open-minded about what we’re doing.”

The objective of the draft not only is to land top-notch prospects in the first few rounds, but to find players in the later rounds that can impact the organization and create valuable depth. On the Red Sox active roster at the moment, Jarren Duran was a seventh-round pick, Kutter Crawford a 16th-rounder and Brandon Walter a 26th-round pick.

“The fact of the matter is in amateur scouting, if you come out of a draft with a handful of big leaguers, you crushed it,” Bloom said. “So the margins are very small and that means just being a little bit better every year. Those rewards pay off so handsomely, when those players get in the big leagues. So it’s something we really push ourselves to do. And yeah, some part of it is about analytical information, player development is another piece of it, and really, scouting is still at the center. It’s really just about having a continuously improving process that takes advantage of all the information that we have that allows us to just be more systematic, be more consistent in our decision making with all of the information that we have.”

As the Red Sox prepare for another draft with high stakes, the organization is relying on Pearson to keep pushing the farm system in the right direction.

“He’s one of the most exceptional young guys I’ve been around in my 25 or 30 years in baseball,” Rikard said. “He’s one of the best listeners I’ve been around. He is so incredibly considerate of others, he seeks people’s input, he has really tremendous leadership skills for a young guy and he packages all that up with a really unique sense of humility that’s pretty rare, honestly.”

(Top photo of Pearson with the 2018 World Series trophy: Courtesy of Devin Pearson)

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