Jim McKew and Alex Jimenez
Portland native Jim McKew, right, with his former Detroit Tigers colleague Alex Jimenez, now minor league operations assistant for the Pittsburgh Pirates. McKew is baseball operations and advanced scouting coordinator of the San Diego Padres. (Courtesy Jim McKew)
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Look no further than Jim McKew to explain what a difference a decade makes in the coaching world.

From the self-described “least qualified Division I baseball coach in the country” to a role in the front office of an MLB franchise, 31-year-old McKew, a Portland native and Cheverus High School graduate, is in his first season as baseball operations and advanced scouting coordinator with the San Diego Padres.

Greg Levinsky“It’s been very enlightening to see what goes into this,” McKew said recently by phone from San Diego after returning from a 10-day road trip that included games in Cincinnati, Pittsburgh, and Cleveland. “First as a fan and then as a lower-level person involved, you have this perception of what goes into it every day and that it’s mystical, magical. Then you get there and you see they’re all still human beings – extremely talented human beings – but that they’re still putting in long hours day to day, working their butts off.”

McKew reports to the Padres front office, but his day-to-day role is heavily involved with the team’s coaching staff, both at home and on the road. He also prepares more than a half-dozen daily reports for manager Bob Melvin. During games, McKew serves as the team’s replay coordinator, communicating with coaches about whether they should challenge a close call. He also works with coaches on their game plan for facing pitchers the Padres will see throughout a series.

“I work closely with the manager, bench coach, and hitting guys,” McKew said. “There’s three wrinkles to it all.”

And as luck would have it, he isn’t the only Portland native with the Padres: Ryan Flaherty, a Deering High School graduate who played eight MLB seasons with three teams, is in his third year with the Padres as an advance scout and development coach.

McKew, the son of longtime Cheverus baseball coach Mac McKew, played baseball for the Stags. After graduating in 2009, he attended Marquette University in Wisconsin, where he worked as a student assistant coach with the men’s basketball team. He also served as an assistant coach with the Cheverus baseball team on college summer breaks (and was this columnist’s coach at the Cheverus summer basketball camp).

After college, McKew worked as the director of baseball operations and first base coach at George Washington University for two years, where head coach Gregg Ritchie, a former major leaguer, proved a sound mentor.

“That’s what got this rolling,” McKew said.

His break into professional baseball came as a player development intern with the Detroit Tigers in 2016. Portlander Dave Littlefield, the organization’s vice president of player development at the time helped make the connection.

After his internship, McKew stuck with the Tigers as minor league video coordinator and development coordinator until last season, when his contract was not renewed because of departmental changes, including Littlefield’s reassignment.

There’s a rule in Major League Baseball that one organization’s staffers cannot reach out to another organization; it’s called tampering.

But as a free agent, McKew reached out to Flaherty and other contacts around baseball and ultimately accepted the Padres’ offer.

His baseball adventure is in full swing (pun intended).