Red Sox setting themselves up for failure by refusing to evolve with free-agent market

BOSTON, MA - OCTOBER 6: Chief Baseball Officer Chaim Bloom of the Boston Red Sox addresses the media during a press conference following the final game of the 2022 season on October 6, 2022 at Fenway Park in Boston, Massachusetts. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
BOSTON, MA - OCTOBER 6: Chief Baseball Officer Chaim Bloom of the Boston Red Sox addresses the media during a press conference following the final game of the 2022 season on October 6, 2022 at Fenway Park in Boston, Massachusetts. (Photo by Billie Weiss/Boston Red Sox/Getty Images) /

The Boston Red Sox haven’t picked up on this free agency trend

Free agency is evolving and the Boston Red Sox have stubbornly refused to adapt to the changing landscape.

MLB teams have combined to spend well over $2 billion on this year’s loaded free-agent class, but the Sox continue to strike out with their top targets due to their reluctance to commit long-term to elite talent.

It wasn’t long ago that teams were applauded for restraint. Massive contract extensions and free-agent deals rarely panned out; Miguel Cabrera, Prince Fielder, Giancarlo Stanton, and Alex Rodriguez’s second contract with the Yankees were cautionary tales that showed the danger of handing out $200+ million contracts that look less like a roster anchor and more like a payroll weight as the player severely declines several years before the contract expires.

The Sox have had their fair share of terrible free-agent decisions but they’ve largely eschewed long-term deals. David Price’s 7-year, $217M deal is the largest total salary the Red Sox have ever committed to any contract, but the longest free-agent contract in franchise history remains Manny Ramirez’s 8-year, $160M signing way back in 2000. However, that contract not only came from an entirely different front office, but from the club’s previous ownership. Boston ended up dumping the salaries of both players – and several of their other biggest contracts – on the Los Angeles Dodgers rather than seeing those decisions through to the end.

While history indicates that clubs are better served by avoiding such long commitments, we’re seeing this approach change in recent years. The shift appears to be at least partially due to how teams view the punitive penalties that result from exceeding the luxury tax. Money isn’t the only concern with the competitive balance tax; loss of draft picks and international signing bonus money piles up for teams that repeatedly dive too deep into tax territory, which can hinder a team’s long-term roster construction. In order to create additional wiggle room beneath the threshold, or reduce the penalties they are paying for going over, teams are showing a willingness to lock up superstar talent to longer deals at a lower average annual value.

In 2019, Bryce Harper signed a 13-year, $330M deal with the Philadelphia Phillies. At the time, it set a new MLB free-agent record for length and guaranteed money. However, the AAV just north of $25M is relatively tame compared to what other superstars have commanded on the open market in recent years. Manny Machado, who is the same age as Harper but lacks his MVP resume, is earning $30M per year on the 10-year contract that he signed with the San Diego Padres that the same offseason. The Phillies tacked on more years to give Harper the record-setting total he wanted while getting a small discount on an annual basis. The setup benefited the Phillies, as they’d never exceeded the luxury tax threshold before; they did so this year for the first time.

The trend has continued this offseason with three more deals of 11+ years. Carlos Correa matched Harper’s 13 years on a $350M deal with the San Francisco Giants that makes him the highest-paid shortstop in MLB history, Trea Turner got 11 years, $300M from the Phillies, and the Padres gave Xander Bogaerts 11 years and $280 million. Aaron Judge set a new record for largest free-agent deal when he re-signed with the Yankees for $360M; his $40M AAV is the most ever for a position player. Judge, who turns 31 in April, is older than the other star players in this crop of free agents so his 9-year deal still follows the same formula as his younger peers. A case can be made that the reigning MVP would’ve earned even more per year if he settled for a shorter contract.

Will these contracts age well? Almost certainly not. It’s doubtful that any of these players will still be performing at a high level as they approach the end of those deals in their late 30s and early 40s. They might even be dead weight for a few years on the back end, but teams are willing to take that risk to have those stars in their primes to aid them in their pursuit of a championship.

It’s nearly impossible to predict a decade into the future. There’s no way to know what the collective bargaining agreement will look like in 2032 and beyond. What we do know that the luxury tax threshold will increase from $233M in 2023 to $244M in 2026, and it’s safe to assume that it will only keep rising. In 2003, the threshold was $117M and by 2013, it had risen to $178M. Why wouldn’t it jump another $50-60M over the next decade? If the large-market teams can all comfortably afford a payroll approaching $300M by that point, wasting $25-28M on a washed-up former star won’t seem quite as much of a burden. The percentage of the payroll for which their salary accounts is almost certain to decrease, somewhat cushioning the blow of paying these players in the twilights of their careers.

This seems to be the mindset driving the top contenders with money to spend. Except for the Red Sox, that is.

Despite claiming for months that Bogaerts was their top priority and saying that they were prepared to spend money to improve a roster that finished last in their division in 2022, the Sox never came close to bringing Bogaerts home. We can harp on their astounding lowball offer last spring spoiling their chances to lock up the star shortstop before he hit the open market, but at the end of the day, their final offer of 6 years, $160 million wasn’t even close to the deal he accepted from the Padres. According to Peter Abraham of The Boston Globe, three or four other teams were willing to offer at least $200M. Essentially every team in the market for a star free-agent shortstop valued Bogaerts more than the Red Sox did after having him in the organization since he was 16 years old.

The $26.6M AAV was more than fair, actually topping what he’ll make with the Padres ($25.4M), but Boston wasn’t willing to extend beyond six years for a 30-year-old shortstop. Understandably, Bogaerts was focused on the total amount of time and money, not AAV, so Boston’s offer ultimately paled in comparison. They never stood a chance. Don’t let them off the hook, though; they didn’t try that hard.

This is the same mistake the Sox made with Mookie Betts between 2018-2020. Their last-ditch offer with a $30M AAV was essentially the same as what he ended up getting from the Dodgers, but the Red Sox held the line on going beyond 10 years. When he declined their offer, they decided they had no choice but to trade him. He ended up getting $365M over 12 years with his new team.

Clearly, the Sox didn’t learn from the Betts fiasco, though they claimed that trading him would put them in a position to never have to make that kind of painful move again. Yet, this offseason, in the prime financial and farm-system spot to go big for Bogaerts, they didn’t. Fans can only hope that they have learned from losing Bogaerts before history repeats itself with Rafael Devers, who is eligible for free agency after the upcoming season. If they aren’t preparing an offer that exceeds $300M for Devers, they shouldn’t bother negotiating; after seeing what Bogaerts got, he has little incentive to even hear another mediocre Sox offer before testing the market next year.

Red Sox CEO/President Sam Kennedy keeps attempting to assure the public that ownership is focused on being competitive in 2023 and beyond, but actions speak louder than words. If a team wants to lock up a star player to an extension or lure one in free agency, they need to be willing to make an offer that makes them a little uncomfortable. They’ll feel uneasy about how the deal looks on the back end, but that’s the price of getting the guy. Top talents aren’t going to settle for a “fair” deal that pays them appropriately during the years they are projected to remain in their prime; they want to be taken care of for the rest of their careers, and billion-dollar baseball clubs can afford to do that, especially as the luxury tax thresholds rise.

The Red Sox have long preached the philosophy of building sustainable success – though it’s yet to materialize, as evidenced by two last-place finishes in three years – and have pointed out that long-term commitments that don’t age well can be counterproductive to that mission. It’s accurate to say that these bloated contracts are win-now moves that will likely hinder the team down the line, but hopeful contenders are making those moves because they want to go the distance, and they can further justify exorbitant spending by projecting that rising payrolls will mitigate the damage of sunk costs down the road. Boston has been slow to buy into that approach and it’s ruining their chances to retain their talented core and improve the roster with elite free-agent talent, damaging in both the short- and long-term.

By refusing to stray from the path they claim will lead to sustainable success, the Red Sox aren’t cultivating sustainable success; they’re ensuring sustainable mediocrity.

Next. 5 worst free-agent contracts in Red Sox history. dark