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Should the Indians trade Francisco Lindor now or later?

As Mookie Betts sits in the trade market, Red Sox Nation and fans of the teams that could make a deal for the former Most Valuable Player will be attuned to every rumor, every scrap of news, real or fake. But the Cleveland Indians' front office will be just as interested as Sam from Southie, the one who lives in the David Ortiz jersey.

Boston's machinations in discussing Betts are bound to inform Cleveland's forthcoming quandary about when to trade another MVP-caliber player, Francisco Lindor. It's not a matter of if the Indians trade Lindor, because logic dictates that yes, they will deal him inevitably. The only real question is when the Indians should do this, with four possible windows.

Lindor now has four-plus years of big league service time, and will become eligible for free agency in fall 2021. Theoretically, he could work out a long-term deal with Cleveland before then, but there is no expectation of that occurring. Lindor turns 26 next week, his place secure among the preeminent players in the sport -- a two-time Gold Glove shortstop who hits with power, runs at high speed and generates runs. He's scored 428 runs over the past four seasons. His intangibles will only add value: Lindor is highly regarded as a person and teammate.

For all of that, for the marketability of his exuberant personality, Lindor will likely get one of the most significant contracts in baseball history. The Indians, a smartly run team with a modest payroll by MLB standards, will not be the team that doles out a $300 million to $450 million contract to one player. Heck, the Indians' $60 million agreement with Edwin Encarnacion proved too obtrusive on their financial landscape. Other Indians, like Jose Ramirez, worked out multiyear deals early in their respective careers, but Lindor is about to go through arbitration for a second time, with an enormous raise imminent over the $10.85 million he made last season.

Rival executives expect the Indians will handle Lindor just as they did Trevor Bauer and Corey Kluber last winter -- they will listen to any offers, and wait for the offer that makes the most sense, at the time that is best for the organization.

The Indians now have four windows in which they could trade him:

  1. This winter, when any interested team would have to pay for two full seasons of production from Lindor.

  2. Next summer, in the weeks leading up to the July 31 trade deadline, at a time when Lindor could impact two pennant races for a contender. Any interested club would view Lindor as a difference-maker and be highly motivated. On the other hand, swapping Lindor in midseason could be particularly painful for the Indians, who might be good enough to reclaim the AL Central title again. Any June or July trade of Lindor would be viewed as a white flag by the fan base.

  3. The winter of 2020-21, when Lindor's value will be high but diminished. Lindor would be just a calendar year removed from free agency, and it's possible that, like Betts, he would be devoted to the idea of testing the market.

  4. The summer of 2020-21 -- again, possibly in the middle of a pennant race. Some club could step up and make an aggressive offer for Lindor.

But in recent years, the trade return for even superstar-caliber talents has been in decline. The Orioles were shocked by how little enthusiasm there was for Manny Machado in their trade talks through the winter of 2017-18, and they later settled for what was regarded as a middling package for Machado during the 2018 season: The Dodgers built a five-player offer around outfielder Yusniel Diaz, a 23-year-old who had an .805 OPS in Double-A last season. When the Pirates marketed Gerrit Cole two winters ago, he was not seen as the transcendent superstar he is now, but still, he was one of the best pitchers available for trade, two years away from free agency -- and the Pirates got four players from Houston for him, including Joe Musgrove and Colin Moran.

This is why other teams predict that whenever the Red Sox sort through the offers they get for Betts this winter, they'll probably be disappointed. "It's hard to see a team stepping up and giving up their best prospects for a guy who's going to walk away in a year," said an NL evaluator. "Especially when he might get $30 million in salary. Who's taking that on, and giving up the level of prospects that Boston would need?"

Boston's choice could be the same Baltimore had with Machado: Trade him for less than what it perceives to be equal value in the winter, or just defer the decision to next summer.

Trading Lindor this winter could yield the most return, particularly when applying a rule of thumb for general managers -- that it's better to trade position players in the offseason, when you might have more potential suitors, than in the summer, when a handful of teams might have that specific need. If Cleveland seriously dangles Lindor now, the Indians might draw ardent interest from the full range of big-market teams -- from the Yankees, the Phillies, the Dodgers, the Cubs, etc.

But a trade of Lindor in the next few months would also sabotage their chances of contending next season, when they could have a good team again, around Shane Bieber, Mike Clevinger, Ramirez, Carlos Santana, and new center fielder Oscar Mercado.

So the Indians will listen, monitor the Betts talks and assess as they prepare for another painful decision.