Theo Epstein isn't coming back to clean up the Red Sox payroll mess.

With the Red Sox season ending in disappointment, the team has a lot of big decisions to make. The first is hiring a new GM – and that may not be as easy as the local media thinks. The thought going around is that the Red Sox will go after former GM Theo Epstein. Epstein, held the job from 2003 to 2011, is still with the Cubs; and has already started making moves to get prepared for their offseason. Why would a GM get ready for his club’s offseason, just to uproot his plans and come back to an organization that he left with bad blood? Granted Larry Lucchino is gone, but it’s been reported that he still has some issues with the big bosses and how they do business.

Epstein’s issues with the organization aside, this team is going into an offseason that may prove to be difficult.One reason for that: in a city that is so used to winning, we may be going into a rebuild. If you consider the fact that whoever takes over will most likely have to trade Mookie, extend Devers, and figure out this god-awful pitching staff - all while cutting the team’s payroll from $240 million to $208 million - Theo would also be getting a manager he didn’t hire, and must deal with players like Jackie Bradley, Jr. whom he’ll need to pay or let go. This most likely means that Bradley, Jr., a Gold Glove Outfielder, will be cut loose; even though the club has one more year of control. If they try to sign him, he’d most likely take the Red Sox to arbitration, and the $8.5 million he made in 2019, could jump up. I’m not a gambling man, but I’d bet money that the Sox will say good-bye to slugger J.D. Martinez, who can opt out and go chase more money elsewhere.

And just like that, the Bridge year is here.

This all comes only a year after the team won a World Series.This felt inevitable; we all knew it was coming, given Dave Dombrowski’s track record of leaving teams decimated after he exits organizations. It’s as if the Red Sox traded their souls to get a World Series, and if by their soul’s you mean their farm system then yes, they did! Now the big question in all this is: how long is this “Bridge year” going to take? How much damage did the Sox do to themselves?

With David Price opting back in last year, and Chris Sale - who looked like a shell of himself this year - commanding about $62 million of the payroll between them, a quarter of the team’s target payroll is already spent. Xander Bogaerts is making $20 million, and the team still has Dustin Pedrioa on the payroll for $13 million. Almost half the Red Sox payroll is taken up by four players, one who may never play again, and two pitchers who fans of the team hope are going to return to form. These issues, combined with not having any young talent to promote, are going to make it more likely that we’re in for a 3 or 4 year rebuild. Meaning the GM they hire this year might not be around to reap the rewards from all their hard work. So why would Theo subject himself to that? He can just stay in Chicago and work on the issues they have there. For whomever the Red Sox Bring in, this is going to be a tricky situation. And no matter how this offseason goes, if the Red Sox aren’t winning next year, fans will not be happy.

Matt McElwain

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