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Will teams in David Price sweepstakes instead turn to Jon Lester?

07.25.14 at 2:58 pm ET
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ST. PETERSBURG, Fla. — The Red Sox and Rays may both assume residence at the bottom of the American League East, but the contrast in the dwellings of the team teams is currently stark.

With three straight losses on their way out of Toronto, the Red Sox‘ last-place standing in the division is becoming more and more rigidly defined by the day. The flicker of optimism about potential contention inspired by the team’s eight wins in nine games has yielded to the reality that it’s so very difficult for a team that has shown only rare bursts of strong play to reassert itself in the playoff hunt. The Sox are 9 1/2 games back in the division, and it feels like they’re 95 games back, as ever winning two out of every three remaining games would net the team just 87 wins — a longshot for the second wild card, let alone the division.

The Rays, meanwhile, are surging. They are 25-11, and so even though they are just 2 1/2 games ahead of the Red Sox, they are hitting their stride in a fashion that validates the widespread view of Tampa Bay as the class of the division. Their seven-game deficit in the division somehow seems like a small fraction of what the Red Sox face.

And so it is that the Friday night pitching matchup of ace left-handers David Price and Jon Lester may represent a pendulum swing with repercussions to be realized throughout baseball. As the Rays surge, they seem increasingly inclined to hold onto Price unless they can command a ransom for an elite pitcher who is under team control for the duration of this season and then all of 2015.

Meanwhile, the Sox are sinking at a time when no ground has been gained in extension talks between Lester and his team. And so, it seems increasingly necessary to ask: Could the prize of the trade market shift from Price to Lester? This is a subject of considerable curiosity to talent evaluators as the July 31 market of tradeable assets gains definition.

Price is 10-7 with a 3.06 ERA, 10.0 strikeouts and just 1.2 walks per nine. He represents a formidable addition for any potential contender for both this year and next, and if an acquiring team wasn’t able to re-sign him, it would still receive a compensatory draft pick for his departure. That’s an enormously valuable asset.

Lester, by contrast, is under contract for just the remainder of this year — with a bit more than $4 million remaining in terms of salary obligations to him, hardly a deal-breaker for any team. As a player who would be dealt mid-year in the season prior to reaching free agency, a team could not make him a qualifying offer for the sake of capturing a draft pick should he depart.

But Lester would offer a dominant presence for the duration of 2014, a 30-year-old who has never pitched better. He doesn’t have a Cy on his shelf, but he’s thrusting himself into the mix quickly for the possibility of one this year. He’s 10-7 with a 2.50 ERA, 9.3 strikeouts and 2.0 walks per nine. He’s been masterful, and he has a track record as one of the top October pitchers not just of this generation but of all time, his 1.97 ERA as an October starter ranking among the top handful ever.

If Price doesn’t move, teams that viewed him as the key to a potential championship run could easily set their sites on Lester and give up a significant haul.

A year ago, after all, the Rangers parted with a major league-ready starter (Justin Grimm), a High-A pitcher with top-of-the-rotation upside (C.J. Edwards), a close-to-the-big-leagues corner bat with huge power potential even if some significant questions about his ability to make contact (Mike Olt) and a reliever (Neal Ramirez) to the Cubs for two-plus months of Matt Garza. Teams will pay for rentals.

“The way we looked at it at the time was, a few things: First of all, we thought the American League was up for grabs. I thought there were a number of good teams. We didn’t think, at that time in July, that there was anyone elite and truly separating from the pack. There was Oakland, Detroit, Tampa, obviously Boston went on to win the whole thing,” Rangers GM Jon Daniels explained on WEEI’s Trade Deadline Show on Thursday night. “We felt we could truly contend with those clubs. We wanted to take a shot. We’d been to the playoffs the previous three years. Wanted to continue that. We also knew the dynamic with the club, we had some free-agent decisions coming up, and we wanted to kind of give it a real shot.

“There’s kind of a taboo on trading for rental players. Obviously, you give up a lot of years of control on the back end. I’m a little bit of the mindset that when you have a chance to win it in front of you, you’d just tasted it and come as close as we did, and knowing how special it is, how unique it is to win and have a chance, of course you’d like longer term control of a player, of course that would be preferable, but you have to take a little bit of a chance. If you’re not completely risk averse, take a little bit of a chance and give yourself a chance to win.”

The Rangers took that shot years ago. Other teams might be open to doing so this year. One evaluator suggested potential return for Lester — given how dominant he’s been this year — could be something along the lines of two top prospects and a mid-level type, with a power bat and outfielder (such as Dodgers prospect Joc Pederson) representing potentially fair return. (The Dodgers, it’s worth noting, have been widely connected as a potential trade destination for Price.) Another evaluator said that the Sox could potentially fetch a top prospect, perhaps a corner power bat or a starter, as the centerpiece of a Lester deal.

One evaluator noted that the Sox could increase their haul by permitting a negotiating window. Yet even as a rental, he could fetch a top prospect like the Mets received when the Giants gave up Zack Wheeler for Carlos Beltran back in 2011.

Ironically, if Lester loses to Price on Friday, it could increase the likelihood that the Rays will be in the thick of the race and thus further strengthen the possibility that Lester becomes the ultimate prize between now and July 31.

There are no guarantees, of course, that the Sox would want to deal him. The team may believe that its best chance to retain his services — and to have an ace who would otherwise be very, very difficult to replace — for the long haul would be by keeping him for the rest of the year.

But suffice it to say that an elite pitching matchup with a fellow top-tier left-hander is not the only intrigue that will surround Lester for the next six days.

Read More: David Price, Jon Lester,
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