Presented By Mooney

Jason McLeod sat next to Theo Epstein on Tuesday night as the Fox Sports 1 camera zoomed in on the Cubs president behind home plate at AT&T Park. A laser-focused, stressed-out Epstein gulped while watching his team trail the San Francisco Giants, perhaps thinking about Johnny Cueto and Madison Bumgarner in an elimination Game 5. 

It became the perfect reaction shot on national TV, an image made for Twitter GIFs, something general manager Jed Hoyer could laugh about after that stunning ninth-inning comeback that ended a National League Division Series: “Yeah, I got a lot of screen shots from various friends…you never know what position you’re going to be in or where your hand’s going to be. You try to tell yourself the cameras might be on. And then you forget every time.”

It framed McLeod on the edge of the picture, but the senior vice president of scouting and player development has been a central figure to the Cubs becoming just the third team in major-league history to win at least 100 games within four years of a 100-loss season.

With the Cubs heading back to the NL Championship Series for the second year in a row, McLeod should be in position to run his own baseball-operations department someday. “No question,” Hoyer says, McLeod is ready to be a GM. McLeod’s name usually surfaces in Internet speculation whenever a top job opens up, but his recent sit-down with the Minnesota Twins has been his only formal interview for a GM job.


Leaving Chicago would have been a difficult decision for McLeod on personal and professional levels, but the Twins ultimately offered the job to Derek Falvey – a 33-year-old administrator who just finished his first season as an assistant GM with the Cleveland Indians – and gave him the elevated title of chief baseball officer.

“If the opportunity presents itself again at some point in the future, then we’ll talk about it then,” McLeod said. “But I just couldn’t be more grateful to be here.” 

By the end of September, chairman Tom Ricketts announced a five-year extension for Epstein, a market-setting deal believed to be worth in the range of $50 million. Hoyer also signed a five-year extension, with McLeod getting two more years tacked onto his deal, keeping the band together (on paper) through the 2021 season.

[SHOP: Gear up, Cubs fans!]

That executive timeline matches up with a spectacular array of on-field talent: Anthony Rizzo, Kris Bryant, Addison Russell, Javier Baez, Kyle Schwarber, plus rookies like Willson Contreras and Albert Almora Jr. who are already gaining valuable playoff experience now. 

“I’m exceptionally grateful,” McLeod said. “All of us are. Look at where we are at this moment in time with this team. I can’t imagine a better environment, a better culture to work at in baseball. We’ve been together a long time. We’re friends. We’re good. We embrace the fact that we are good. And we challenge ourselves to be even better.”

Epstein’s style is to listen to a cross-section of voices and mine as many sources of information as possible, but he goes way back with McLeod, to the beginning stages of their careers in the 1990s with the San Diego Padres. At a ground zero for the rebuild, Epstein memorably put it this way during an introductory press conference in the fall of 2011: “Jason McLeod is the rarest commodity in the industry. He’s an impact evaluator of baseball talent.”

McLeod’s first draft with the Boston Red Sox produced Dustin Pedroia, a 2007 American League Rookie of the Year and 2008 MVP, a back-to-back feat that Bryant might replicate in the NL. McLeod also became involved in the drafting of pieces – for Boston’s 2007 World Series team or elsewhere – like Rizzo, Jacoby Ellsbury, Jed Lowrie, Clay Buchholz and Josh Reddick.  

McLeod, a former minor-league pitcher, isn’t some propeller-head. He comes across as someone you would have a beer with, an easygoing personality that meshes with scouts and staffers. But he can also speak to an ownership level, talking the corporate language of systems, processes and analytics. Working in Boston and Chicago has made him comfortable around the media.


McLeod withdrew his name from consideration while his hometown Padres searched for a GM in the middle of the 2014 season, saying he didn’t want to leave with unfinished business and miss being part of a World Series blowout in Wrigleyville.

San Diego hired A.J. Preller, who is currently serving a 30-day suspension after a Major League Baseball investigation into how he mishandled the medical information during the Drew Pomeranz trade with the Red Sox. The Arizona Diamondbacks – a franchise that can match the Padres in terms of dysfunction and instability – are now looking for a new baseball boss after firing Dave Stewart and sidelining Tony La Russa.    

McLeod isn’t seen as a fit in Arizona. For now, McLeod plans to watch the scouting-and-player-development machine Epstein promised to build on the North Side, seeing how all these magnificent talents grow up, while staying close to his family in the Chicago area. But someday, the TV cameras might be looking for McLeod in the stands during an emotionally draining playoff game.