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Two questions confront the Red Sox with Mookie Betts, both with potentially wrenching answers. Do they sign him? Do they trade him? The responses will shape the organization for years.

The dilemma is again in the foreground thanks to the revelation (initially reported by The Athletic, confirmed by major league sources) that the Sox have talked to the Padres about trading Betts. Talks between the Sox and Dodgers about Betts, meanwhile, are still “lingering,” in the words of one major league source.

The Sox have said all offseason that they’ll listen to trade proposals on Betts. That hasn’t changed. How could that be?

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No one denies Betts’s place as one of the best players in the game. The 27-year-old is a franchise player in every sense of the word: A recognizable first-name star who was drafted and developed by the Sox, a preeminent five-tool talent who has performed at All-Star to MVP levels over most of the last five years, a team leader who puts in the effort to be great every day.

Franchises go generations without seeing such a well-rounded player who performs so consistently. His past is dazzling. But that doesn’t mean his future is clear.

Betts is within a year of getting a long-term deal that should be worth well over $300 million, perhaps even surpassing $400 million. The Sox have approached him multiple times about long-term deals; each time, Betts has declined, intent on realizing his market potential.

The Red Sox possess the resources to pursue the most expensive players in the game. Yet robust franchise revenues don’t mean that the team’s decision about his future is easy.

“It’s almost like it’s a legacy issue, not only for the player but also for the organization,” Cardinals president of baseball operations John Mozeliak said earlier this offseason. “You agonize over those types of decisions.”

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Historically speaking

The ability to spend hundreds of millions of dollars doesn’t necessarily mean that doing so is good business. The Sox have paid plenty of money to wash their hands of deals for Manny Ramirez, Julio Lugo, Carl Crawford, Josh Beckett, Adrian Gonzalez, Pablo Sandoval, and Hanley Ramirez. There’s a good chance that Dustin Pedroia will play just nine big league games over the final four seasons of his eight-year, $110 million deal.

Long-term deals for franchise players feature significant, inherent risk, particularly in their final years. No matter how good a player is when he signs, the effect of a nine-figure contract can be crushing for an organization if he can’t play at its end.

“You go into [a long-term deal] knowing that there are risks. There are performance risks. There are health risks. There will ultimately be age risks that will manifest themselves in a loss of performance. That’s the reality. You bake all that into your decision-making,” said Phillies GM Matt Klentak, who signed Bryce Harper to a 13-year, $330 million deal last winter. “You have to be aware that you’re going to have some good years and potentially some bad years, and you’re not always going to know when they’re coming.”

The Phillies decided Bryce Harper was worth the risk of a 13-year, $330 million contract.
The Phillies decided Bryce Harper was worth the risk of a 13-year, $330 million contract.Nick Wass/FR67404 AP via AP

Prior to this offseason, there were 85 contracts of at least $100 million in big league history, with just under half (42) of those having reached completion through either the expiration of a contract, a player’s decision to opt-out or retire in the middle of it, a team’s decision to release a player (sometimes after he’d been traded), or a mid-contract extension that overrode the initial deal.

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Of those 42, 13 (31 percent) produced tremendous payoff, an average of 4.0 Wins Above Replacement (WAR) or better per season in the calculations of Baseball-Reference.com. (Caveat: four of those 13 performances came from players who opted out mid-deal.) That’s at or near Hall of Fame-level production.

Derek Jeter, for instance, averaged 4.1 WAR over the 10-year deal he signed with the Yankees one year before becoming eligible for free agency. If Betts sustains such levels, he’ll justify virtually any contract he gets.

Another 11 players (26 percent) produced between 2.0 and 3.9 WAR — some star-caliber performances and solid production over most of the contracts, but with some bad seasons thrown into the mix, with roughly one out of every three seasons of those deals yielding a WAR of less than 1.0. At times, these contracts delivered tolerable value; at others, teams would have preferred payroll flexibility to the player.

And then there is the outcome that prompts sleeplessness for teams: Disaster, with 18 out of 42 (43 percent) contracts in which players averaged 1.5 WAR or less — less production than an average everyday player over the life of their deals.

Return on investment A look at the performance of MLB players during the 42 completed deals of at least $100 million.
WAR PER SEASON PLAYERS
4+ WAR 13
2-3.99 WAR 11
0-1.99 WAR 17
Negative 1
SOURCE: Cot's Contracts, MLBTradeRumors.com, Baseball-Reference.com

The profiles of the players who struggled are varied — starting pitchers, power hitters, speedsters, great athletes. But a lot of blockbuster signings ended in busts. Underscoring that point, 17 of the 42 completed $100 million deals (40 percent) ended with the player being released or traded — with teams typically subsidizing someone else to take a player once deemed worthy of a franchise contract.

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Even teams that can theoretically afford megacontracts have recognized the need to draw the line somewhere. The Cardinals did so when Albert Pujols — right after leading St. Louis to the 2011 World Series — left for the Angels on a 10-year, $240 million deal. Walking away from him was the right thing, but still sickening.

“Trying to find a way to make it work and then ultimately not having it work out can be painful,” said Mozeliak of the Pujols negotiations. “I think back to that time and just remember it was very stressful, a lot of anxious moments.”

The Yankees didn’t enjoy seeing Robinson Cano leave on a 10-year, $240 million deal with the Mariners. They wanted to keep him but couldn’t find common ground — and have subsequently been rewarded for their discipline.

“[Cano and his agents] had certain numbers in their mind,” recalled Yankees GM Brian Cashman. “It was not a number we were even going to approach. They got it, and it crippled the Mariners. We’ve all been there — made mistakes that backfired.”

The Yankees wanted to keep Robinson Cano, but not for the 10 years and $240 million the Mariners offered.
The Yankees wanted to keep Robinson Cano, but not for the 10 years and $240 million the Mariners offered.File

Cano’s contract proved sufficiently burdensome to Seattle that they gave up a very good player — closer Edwin Diaz — and agreed to pay down a sizable chunk of its last five years to achieve greater flexibility. (Seattle also landed a very impressive prospect package from the Mets to deal Cano and Diaz.)

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There is potentially enormous reward when players sign franchise deals and sustain their elite performances. Jeter’s value to the Yankees vastly exceeded what he made over his 10-year deal. Alex Rodriguez was a seven-time All-Star and three-time MVP for the Rangers and Yankees (albeit with admitted use of PEDs to help him to such levels) before opting out of his historic deal after seven years.

Manny Ramirez lived up to his eight-year, $160 million deal with the Red Sox (though like Rodriguez, Ramirez’s performance is clouded by positive tests for PED use later in his career). Carlos Beltran — whose skill set and age at free agency merit some comparison to that of Betts — was a standout for much of the seven-year deal he signed with the Mets.

“You don’t get the player [without assuming risk],” said Rangers GM Jon Daniels, whose team benefited from signing Adrian Beltre to a six-year, $96 million deal from 2011-16. “If they’re fortunate enough to stay healthy and produce, then they help propel you quite a bit.”

But teams can’t be assured of such an outcome. Eventually, stars can become roster burdens whose performance declines and contracts impede a team’s competitiveness.

But what is the alternative?

Trading a franchise player

In the constant effort to balance short- and long-term interests, teams inevitably confront the question of whether a chance to improve their long-term outlook with an infusion of young, cheap, talented players with six-plus years of team control surpasses the value of better odds of success in a single year (and sometimes more) with a franchise player. It’s not a fun exercise.

“It was extremely painful,” Diamondbacks GM Mike Hazen said of trading Paul Goldschmidt last winter, prior to the first baseman’s walk year.

“That decision, making it and executing it, was exceptionally difficult,” said Rays GM Erik Neander, who dealt Evan Longoria to the Giants prior to the 2018 season — at a time when he and current Red Sox chief baseball officer Chaim Bloom led the baseball operations department. “Evan was someone who gave so much to our community and our organization — a model citizen, a model player, the template of what you want. Even the thought of considering sending him to a different team was really hard.”

Yet the Diamondbacks and Rays face different financial dilemmas than the Red Sox, with different financial limitations. How can a big-market team contemplate moving a player like Betts?

Dodgers president of baseball operations Andrew Friedman dealt a face-of-the-franchise player in Matt Kemp prior to the 2015 season, but he did so at a time when Kemp’s injuries had him in a clear state of decline.

Betts isn’t in decline. He’s 27 and a perennial All-Star. It’s hard to remember the last time a big-market team in the middle of a playoff/title window traded such a player prior to a season in which it intended to contend.

Ken Griffey Jr. might be the closest parallel — though Griffey had made public requests for a trade to the Reds before Seattle sent him to Cincinnati in 2000. Betts hasn’t done anything like that. And while Seattle initially withstood the departures of Griffey and Rodriguez in back-to-back years to reach the ALCS in 2000 and 2001, they haven’t been back to the playoffs in 18 years.

The Mariners dealt Ken Griffey Jr. when he made public requests to be traded to the Reds.
The Mariners dealt Ken Griffey Jr. when he made public requests to be traded to the Reds.File/Associated Press

The third way

Could Seattle have gone down a different path? Teams don’t have to trade a franchise player just because he’s entering his final season of contractual control and there’s skepticism about the ability to re-sign him.

The Cardinals retained Pujols in his walk year, a decision that paid off with a title in 2011. The Astros kept Gerrit Cole last year; he nearly pitched them to a title, but they were beaten by the Nationals — who featured stars Stephen Strasburg and Anthony Rendon in the final year of contractual control.

The idea of “letting a player walk for nothing” fails to account for how a superstar can elevate a team from postseason to championship contention. The Nationals don’t exactly feel as if they got “just” a draft pick (in this case, one that will come after the second round) when Rendon left this winter.

So how should the Red Sox proceed? There is no certainty surrounding an answer — beyond the fact that every choice will come with its own discomforts.


Alex Speier can be reached at alex.speier@globe.com. Follow him on twitter at @alexspeier.