Mixed emotions for Cubs VP McLeod watching Red Sox win title

Mixed emotions for Cubs VP McLeod watching Red Sox win title
November 19, 2013, 10:30 pm
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On the same day the Cubs put a mock-up sign over the right-field bleachers, the Boston Red Sox celebrated their third World Series title in the last 10 seasons.

While the Cubs fired another warning shot at the Wrigleyville rooftops, the Red Sox finished off the St. Louis Cardinals and partied inside Fenway Park. That shows the distance between these two iconic franchises more than the 1,000 miles separating Sheffield Avenue and Yawkey Way.

But Cubs fans straining to see the light at the end of the tunnel can still look at the Red Sox. Theo Epstein didn’t leave an organization in ruins. Heading into Year 3 of a full-scale rebuild, Cubs executives can use this as another billboard.

“It was definitely mixed emotions,” said Jason McLeod, the senior vice president of scouting and player development. “You remember the feeling of being there when we won.”

[RELATED: Theo happy, proud for former Boston colleagues]

McLeod worked in Boston’s scouting department from 2003 to 2009, a time when the Red Sox drafted Dustin Pedroia, Jacoby Ellsbury, Clay Buchholz and Will Middlebrooks.

“You feel great for your friends that are over there,” McLeod said. “At the same time, you miss it, too. I’m not going to lie to you about that. So it works two ways. You’re like: ‘God, I remember what that was about. I remember when we selected those guys. I remember the development plans for those guys.’

“Hopefully, we’re going to have that feeling again. That’s what drives us. It’s possible, so we just got to go make it happen.”

McLeod – who spent two seasons as Jed Hoyer’s assistant general manager with the San Diego Padres – now has fingerprints on three organizations that placed top-six in Baseball America’s recent farm-system rankings.

[MORE: Starting with Samardzija, Cubs will be in a position to make deals]

During a spring-training tour last March, ESPN analyst Jim Bowden identified McLeod as a top GM prospect. (McLeod said that amused his buddies and had them wondering what he owed Bowden.)

“You try not to pay attention to it,” McLeod said, “because there’s too many things going on here to keep your mind on and if that time comes we’ll deal with it. I can tell you that this is the greatest challenge in the history of North American sports now.

“It keeps all of us exceptionally energized about what it is we’re trying to do.

"I don’t really think about it, to be honest. ... I feel so lucky and humbled that I get to work with Theo and Jed, two guys who I think are exceptionally talented, but are also friends of mine. And then having the ownership group here and this city, this challenge, it’s like I couldn’t be in a better spot.

“If something happens unforeseen or whatnot and someone calls, then we’ll just deal with it then.”  

McLeod gave that answer in late September, but it has been a quiet offseason at the industry’s executive level. The Cubs spent October looking for Dale Sveum’s replacement.

[MORE: Scott Boras rips The Plan as Cubs avoid big free agents]

McLeod – along with farm director Brandon Hyde and assistant GM Randy Bush – interviewed Padres bench coach Rick Renteria in California as part of a managerial search that focused on players who aren’t in the big leagues yet.

“You’re not giving up on today, but you’re looking long-term,” McLeod said. “Hopefully, we don’t have to do this (again) for a very, very long time, if ever. I just feel really, really good about the hire.   

“(Renteria’s) a positive guy, for sure. He enjoys what he’s doing. But don’t make the mistake of (thinking he’s) being naïve or gullible. He believes in a process and he knows who he is more than anything.”

The Cubs have a new manager, an elite farm system and the Arizona Fall League’s MVP in Kris Bryant. After losing 96 games, they dream about a lineup powered by Javier Baez, Jorge Soler and Albert Almora and a rotation fronted by C.J. Edwards and Pierce Johnson.

[RELATED -- Cubs send message to Kris Bryant: Keep dominating]

The Cubs didn’t have Boston’s Hall of Fame core already in place and it’s been years since they spent like a big-market team. But there’s still enough Red Sox pedigree to lend credibility to Epstein’s hope-and-change message. 

“No doubt, it was tough,” McLeod said. “There were some tough moments where we were like: ‘Oh, it’s so bittersweet.’ But more than anything you’re happy. You feel good about what you did, what you contributed to and you just hope you can do it again.”