David Ortiz knows better than anyone how stupid the Red Sox are being with Xander Bogaerts

The Red Sox are at risk of losing another franchise-icon-in-the-making in Xander Bogaerts. David Ortiz wants what’s best for the fans.

History repeats itself in Boston.

Baseball, in many ways, is cyclical. No team is great forever. For 86 years, the cycle in Boston was one of only heartbreak, watching the Red Sox get almost all the way to glory, only to lose in heartbreaking, astounding, confounding fashion at the last minute, usually in a Game 7. But since the current ownership group purchased the team twenty years ago, repetition comes in the greatest form, championship, and the worst, the loss of beloved players.

Throughout it all, fans watch happily or helplessly, strapped into a roller coaster ride many have been on since birth. They have no say in matters and no control, which would be fine, if the organization didn’t keep making the same mistake over and over. As Taylor Swift famously sings, “I think I’ve seen this film before / And I didn’t like the ending.” Red Sox Nation has been here many times over the last two decades.

Red Sox at risk of losing Xander Bogaerts because of own doing

Right now, the player in question is Xander Bogaerts, their homegrown, unofficial captain and team leader who’s been with the organization since he was 16. The Sox are lowballing him after exceeding the luxury tax threshold to sign fellow shortstop Trevor Story to a six-year deal.

Before him, there was Jon Lester, one of Boston’s only great homegrown pitchers of the last two decades. He battled cancer in 2006, went into remission, and led the team to championship in 2007, and again in 2013. The Sox dealt him to Oakland at the 2014 trade deadline, and he went on to win another ring with the Chicago Cubs, their first in 108 years.

Then, Mookie Betts, whom the Red Sox lowballed right after he led them to their fourth championship in fifteen years in 2018. That year, he became the first player in MLB history to win a Silver Slugger, Gold Glove, batting title, MVP award, and World Series in the same season. He’d been an All-Star, Silver Slugger, and Gold Glove winner every year from 2016-19 when the Sox traded him to the Los Angeles Dodgers in the spring of 2020. That fall, he led the Dodgers to their first championship since 1988.

In between, the Red Sox shelled out for several free agents, none of whom panned out. In December 2010, the Red Sox signed Carl Crawford to a seven-year contract with a hefty $142M price tag. The following spring, they gave Adrian González a seven-year contract for $154M. Both were traded to the Dodgers on August 25, 2012, not even lasting two years into their deals.

And of course, there was Pablo Sandoval, the slugging infielder who won three rings with the San Francisco Giants in 2010, 2012, and 2014. When he became a free agent after the last championship, the Sox inked him to a five-year deal worth $90M. He might be the biggest free-agent bust in franchise history. On July 14, 2017, the Sox designated him for assignment, and five days later, he was released. His time here had soured to such an extent that the Sox were willing to pay the remainder of his salary just to get rid of him.

Red Sox: Will history repeat itself?

The pattern is clear to everyone but ownership. They either don’t see it, which seems impossible, or more likely, they don’t care. To them, the grass is always greener in somebody else’s ballpark. An unproven free agent is inexplicably better than a proven star.

No one knows the pattern better than David Ortiz, who led the Red Sox through championship years and last-place seasons, cycling from first to worst and back again for more than a decade. He watched his homegrown teammates leave, and free-agent busts take their place.

He doesn’t want that to happen to Xander Bogaerts.

Earlier this week, Ortiz made an appearance at one of his many philanthropic endeavors, the David Ortiz Boston Heart Classic at Brae Burn Country Club in Newton, MA, and told reporters, “It would be stupid to let a guy like that go, to be honest with you. I played with Bogey for a long time and Bogaerts is the perfect player for any organization. He will represent this organization on and off the field. So that conversation needs to take place at any time.”

Ortiz is still technically under a contract of his own with the club. They signed him to a lifetime deal of sorts in 2017, less than a year after he retired. But in his book, Papi, he writes that his contract disputes with the Sox were frustrating, and he often took a discount to stay with the team he loved.

Bogaerts has been with the organization since he was 16 years old. In his first decade of big-league play, he’s helped the team win two of their four rings in this century, been a three-time All-Star, and four-time Silver Slugger. More importantly, he’s a leader in this clubhouse, and especially, a mentor to Rafael Devers, whom they also need to pay.

I don’t even think Bogaerts wants an outrageous deal; he just wants what’s fair. He approached the Sox about an extension in 2019, and signed a very team-friendly deal. Since then, he’s watched fellow shortstops around the league sign enormous contracts and extensions, and he’s as good, if not better than them. He’s made it abundantly clear that he wants to spend his entire career in a Red Sox uniform, but he’s also more than earned the right to ask for a raise.

A player spending their entire career with one team is almost unheard of nowadays. But if anyone should be Red Sox for life, it’s Bogaerts.

Ortiz agrees:

“That’s a keeper. That guy is a keeper. Believe it or not. I don’t want to hear the B.S. that there’s somebody else out there in the market better. I know what I’m getting from Bogaerts. That’s why I want Bogaerts. I know what I’m getting from him. I prefer to take that over, ‘Let’s see what is coming.’ In my clubhouse, on my team, I want him at shortstop for the next whatever (amount of years) because I know what I’m getting from him.”

It’s time for the Sox to break this pattern. If only because it’s pretty embarrassing to be called stupid by David Ortiz.