In 2014, the Boston Red Sox traded Jon Lester to the Oakland A’s after lowballing him in extension talks.
That ripple effect of that mistake impacts the Red Sox to this day, and if the latest reports are true, that’s not going to change anytime soon.
Former Red Sox star Jon Lester is helping the Cubs pursue Xander Bogaerts
Lester is reportedly helping the Cubs entice Bogaerts, and it’s not hard to guess what they’re bonding over. Each player brought the city a pair of trophies and was rewarded for their efforts with insulting lowball offers. The Sox traded Lester and might have tried to trade Bogaerts this summer, if not for his full no-trade clause. Bogaerts admitted at the deadline that he was relieved when the Sox told him they weren’t trying to trade him, a concern that should never have even crossed his mind.
Losing Bogaerts to the Cubs because of Lester would be the ultimate double dose of karma for the Sox, though they don’t seem to care. They pushed both players out the door, and now, the Cubs have a welcome party full of old friends from Bogaerts’ early years just waiting to treat him right. His 2013 teammates, David Ross and Mike Napoli, are Cubs manager and first-base coach, respectively. Former Red Sox assistant GM Jed Hoyer is the team president, who briefly overlapped with a 16-year-old Bogaerts.
According to Mark Feinsand of MLB.com, Hoyer has the “green light” from ownership to spend big. So big, in fact, that he reports the Cubs could sign Bogaerts and fellow shortstop Dansby Swanson, though it would hinge on Bogaerts moving to third base, which feels unlikely.
Because the Sox lost Lester, they over-corrected by overspending on David Price. Seven years, $215M, still the richest contract in franchise history and the largest pitching contract in MLB history at the time.
The following season, Lester helped the Cubs win their first World Series in over a century, against the team who swept the Sox in the ALDS. Meanwhile, Price didn’t meet Boston’s lofty expectations, so they acquired Chris Sale from the Chicago White Sox ahead of the 2017 season. Again, they won the division and lost in the ALDS.
In 2018, things came together for the Sox. For a brief, but brilliant shining moment, they were the best team in baseball and won their fourth championship in fifteen years.
But the payroll was enormous and the top level of the farm system was depleted, and then, ownership cut off Dave Dombrowski’s spending. When the starting rotation fell apart in 2019, the Sox missed the postseason. In order to avoid future luxury tax penalties, they paid the Los Angeles Dodgers to take Price and sweetened the deal with Mookie Betts.
Yes, in a way, losing Lester contributed to losing Betts. And because the Sox have apparently not learned from losing either of them, they could very well lose Bogaerts, too. At this point, their handling of the situation and mistreatment of such a respected player proves they deserve to lose him.
The Sox have established a pattern of lowballing their homegrown proven champions while throwing money at free agents, who almost never pan out. This is their chance to break the chain. The problem is, they just don’t seem to care.
Red Sox Winter Meetings tracker: rumors, free agents, live updates
MLB's Winter Meetings are underway. Keep up with every Red Sox rumor, signing, and trade, as well as Xander Bogaerts updates and other important news.