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The Red Sox Season Is Over But They're Still Losing Talent

The Red Sox last lost on the field on September 30. Three weeks later, they're still losing off of it. 

For the second straight season, a young front-office fixture has left the organization. 

Last year, VP and Assistant GM Paul Toboni left to become the Nats President of Baseball Ops. Toboni gets a lot of credit for the drafting of guys like Roman Anthony. At just 35, the Nats made him one of the youngest in MLB to hold that President of Baseball Ops title. 

His former co-worker Taylor Smith now has that distinction. The A's just plucked him out of the Red Sox front office, and at 31, he's now the youngest head of operations in MLB. Mr. Moneyball himself, Billy Beane, seems to like the move. 


“It’s exciting to welcome Taylor to the Athletics as the new President of Baseball Operations. He is a smart, creative baseball mind with the leadership skills to build a cutting-edge, winning organization that our fans can be proud of for years to come. I couldn’t be more excited about the A’s future,” said the current A's advisor. 

If you're a Red Sox fan, you can look at this a couple of ways. 

Glass Half Full

Good teams lose talented people

Luke Murray just got the Boston College basketball job. He got that job, in part, because UConn has been so good under Dan Hurley. People want to hire people from successful organizations. People wanted Bill Belichick because of his success with Bill Parcells. Duh. 

Boston Globe. Getty Images.

Glass Half Empty

Talented people are taking the first chance they get to bolt from the Red Sox because they don't want to work there anymore

These guys left for good jobs, I get it. But remember that Craig Breslow was the team's 11th or 12th option for the team's President of Baseball Ops role after people kept saying no to the job - and, in fact, not even going for an interview. Is there an issue working with this ownership? 

Or maybe working for Breslow. The Boston Globe reported during this season that "multiple officials" within the organization believe Breslow "might benefit from having an interpreter of sorts."

"Over the past month, Breslow has made a concerted effort to have more conversations with players and clubhouse-level personnel, he said," Tim Healey wrote back in June. "Part of the point is telling them he cares about them and winning and he is there to support them."

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This is a working environment that reportedly led a scout to call Breslow a "fucking stiff" over Zoom just last season. There have Are his coworkers unhappy with Breslow's front office? 

Or maybe they know the team is not planning to spend much. From the Globe over the weekend, in the team adding with the looming MLB Labor Dispute. 

That doesn’t rule out the possibility of roster changes — particularly trades and nontendering of players — before a lockout. Still, if precedent holds, the Sox seem unlikely to add significant payroll until after the new CBA is negotiated, if then. 

Yeah, no way John Henry opens his checkbook until he knows the new rules. God forbid the Big Market Red Sox act like a Big Market team….

Boston Globe. Getty Images.

I am NOT a Breslow guy. He's done a good job finding pitching, but I really doubt the team's next World Series will be under his watch. 

And losing Toboni and Smith in back-to-back offseasons makes me think more than ever that Craiggers is running the whole show. 

Maybe Sox fans will ignore this. Or spin it into some sort of positive about the health of the organization. Me? Well, watching your youngest, most highly regarded front-office people leave for other organizations in consecutive years doesn't feel like a great thing…especially when I don't have much faith in the guy still here running the show.