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Cliff Lee’s precedent for an improbable shoot-the-moon scenario for Jon Lester, Red Sox

07.26.14 at 10:16 am ET
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ST. PETERSBURG, Fla. — Jon Lester saw no reason to dismiss the idea. Get traded by the Red Sox in July, then re-sign with the club four months down the line?

“Why not?” he said in the Red Sox clubhouse after a 6-4 defeat to the Rays. “This is what I know. This is what I love.”

The idea of a player getting dealt only to turn around and re-sign as a free agent is unusual — but not unprecedented. In 1993, Rickey Henderson was sent by the A’s to the Blue Jays for Steve Karsay; Henderson helped the Jays to the second of back-to-back World Series wins, then turned around and re-signed with Oakland that offseason. In 1995, the Twins traded closer Rick Aguilera to the Red Sox for Frankie Rodriguez in July; that winter, Aguilera re-signed with Minnesota.

Yet another example of a more recent ilk may be more in line with a best-case scenario for the Red Sox and Lester. After the 2009 season, the Phillies sent left-hander Cliff Lee to the Mariners as part of a three-team deal that landed Roy Halladay in Philadelphia. One year later, teams were coming at Lee with six- and even seven-year offers. Yet even with the Yankees seemingly willing to open up the vault for Lee, the left-hander decided to return to the Phillies on a five-year, $120 million deal.

The $24 million average annual value of the deal may have been slightly north of the AAV offered elsewhere, but Lee left tens of millions of guaranteed dollars and at least one guaranteed year on the table in order to return to a place he’d enjoyed.

“I never wanted to leave this place in the first place,” Lee explained at the press conference heralding his arrival.

In many ways, that precedent might be the most intriguing one for the Sox and Lester. At a time when an elite prospect could be valued at tens of millions of dollars (consider that Jose Abreu — a player who at the time came with a relevant degree of risk — signed for six years and $68 million) given his potential performance relative and low salary, the idea of acquiring an elite young talent in exchange for the next two months of Lester’s services has to be a significant consideration for the Red Sox. But if the Sox could then convince Lester to return to a contract whose average annual value was in line with prevailing market values, while getting him to consider leaving a year on the table (as Lee did), then the Sox have a scenario in which they could have their proverbial cake and eat it, too.

Of course, given the Sox’ caution — backed by mountains of bad contracts as evidence — regarding the length of a deal, even a five-year commitment to Lester during his age 31-35 seasons might represent too long a commitment for the team’s comfort. (It is worth noting, after all, that Lee — whose deal spanned his age 32-36 seasons — just missed two months with an injured elbow.) Perhaps the trade/re-sign cake strategy represents little more than pie in the sky.

But, at the least, there is some precedent to contemplate it — a sort of window into a bakery of available trade deadline options.

Read More: Cliff Lee, Jon Lester, rick aguilera, Rickey Henderson
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