ALEX BREGMAN: Does a mid-season extension make sense?
How much sense does an early Red Sox pursuit of an extension make?
By Terry Cushman Jr
RED SOX HAVE ALL THE LEVERAGE
All last winter, Scott Boras told reporters that his client, Alex Bregman, was not willing to sign a short term deal.
The Astros were willing to offer a six year deal worth six years, $150M. The Tigers in the post Mike Illitch era, made an uncharacteristically valiant effort with a six year $171M deal.
But in the end Bregman and Boras caved, and agreed to a short term deal with a high average annual value worth $40 million a year thru 2027 with opt outs following the first two years.
The thirty one year old former Astro has now missed 36 games and counting due to his second significant quad injury, and firmly seems to believe being on the injured list for six weeks is the ideal time to ask for an extension.
THE TIMING
The Rafael Devers trade sent shockwaves through the sport on June 15th, as well as the Red Sox clubhouse. As shocking as it seemed, it may have been viewed as erratic to a veteran player like Bregman.
An inexperienced second year Chief Baseball Officer, Craig Breslow, who based on reports, does not get along with many members of his front office, is calling the shots.
If you’re sitting in Bregman’s place, is there a possibility you could also be traded? Impossible to completely rule it out.
John Henry freed up $254M by aunthorizing the Devers move.
Would freeing up the remaining $93M of Bregman’s deal over the next three years sound equally as appetizing to the owner of the Boston Red Sox? Probably.
An extension this first week of July would give the injured Boston third baseman assurances that he still remains part of the long term plans.
In other words, he plays for a team that is closer to last place than first place. He is literally useless at the moment. Has no control over his future. And he’s trying to influence a bigger margin of control.
DOES AN EXTENSION RIGHT NOW MAKE SENSE?
No.
The Red Sox should handle the situation exactly as they did with J.D. Martinez. In four of his five seasons in a Boston uniform, he made the all star team.
In each year of his opt out eligibility the expectation was that he would in fact opt out. Scott Boras would work the phones leading up to the opt out deadline, but no teams were willing to overpay beyond the balance of his original 5/$110M contract.
Martinez was one year younger than Bregman at the time of his signing. But far more durable. Never playing fewer than 139 games.
Is there a possibility Bregman still opts out? Yes.
But will there be a team eager to sign him to a six year deal at huge money? Most likely not.
If I’m wrong, he would still most likely be forced to wait out a frustrating free agency period. Only to sign another deal in mid February with a less than desirable destination.
The Red Sox waited out the entire winter to sign Bregman to a deal on THEIR terms. A deal that limits the long term risk, and maximizes the best remaining production that he has left.
It was a SMART deal. So why pivot and sign him to a dumb one?
Scott Boras clearly recognizes that Breslow is desperately in need of some good press. To turn the narrative of an extremely tumultuous season.
The major road block in Boras’ way is John Henry, who very likely would have to approve such an extension.
Shortsighted Red Sox fans may very well be attached to Bregman, and obsessed with the idea of extending him.
But did Henry get attached to Jon Lester? Or Xander Bogaerts? How about Mookie Betts? The answer is no.
It’s very possible that the reclusive Red Sox owner already views the Bregman deal similarly to two other 30+ year old free agents in Masataka Yoshida and Trevor Story.
The Red Sox have two pathways:
1. Retain their leverage.
2. Repeat the mistakes of the past.
Or perhaps they simply trade him to the Detroit Tigers, who still need a third baseman, and that one final piece to slam the door on the American League?