If Red Sox Keep Losing, Say Goodbye to John Lackey, Maybe Jon Lester

Sign up for Boston Globe's 108 Stitches newsletter and be entered to win a four-pack of tickets to the Red Sox home game on August 28th.  Get everything baseball, straight from the desk of Alex Speier. Mon-Fri during the season, and weekly in the offseason.

If things continue to go down the same path, it’s going to come time for the Red Sox to ask themselves a complicated question.

What can they get for Jon Lester?

Major League Baseball’s trading deadline is still eight weeks away, but the 27-32 Red Sox may come to a crossroads long before July 31. Should they try and deal their ace to a contender, selling Lester’s impeccable postseason record as a means to what would amount to a two-month rental before he hits free agency? Do they try and work out a long-term deal before then, with the increasing knowledge that Lester’s price tag is likely going to be in excess of the $144 million that Max Scherzer turned down from the Tigers in March? Or is Ben Cherington content in letting Lester test the free agent market, and receiving a first-round draft pick from the team he signs with as a tiny semblance of compensation?


Despite Larry Lucchino’s claim last week that the team was willing to resume talks with the lefty and his agents, Sam and Seth Levinson, during the season, the conversations might as well be about which guy they think has the best chance on “The Bachelorette.” Because they’ll be wasting their breath in terms of Lester signing a deal before other teams get their claws on him.

“Great,” Lester said when informed of Lucchino’s statement. “Whatever.
“This is far from what we need to be thinking about right now. We need to be thinking about playing good baseball and getting back to the top of the standings in the East and continue from there.”
Lester was coming off a dominant effort in his last start against the Tampa Bay Rays last Sunday when he made those comments, leading the Red Sox to a 4-0 victory, their seventh in a row after having lost 10 straight. Boston was two games under .500, and six games behind the front-running Blue Jays in the American League East.
Five days later, the Red Sox have lost three straight, and three games in the division, where they now face a nine-game deficit. For every up this season, there is a down, and the dips are longer, deeper, and more telling than every bright spot.
If the Sox can’t climb back into respectability, John Lackey is an obvious candidate for the trade market. Because he missed all of 2011 with Tommy John surgery, Lackey will make the club minimum in 2015, $500,000, and interested teams would have the hurler for their playoff run in 2014 and at a bargain basement price for next season, which will likely make him the most sought-after starting pitcher on this summer’s trade market. That means Boston can sit back and allow teams to outbid each other. It also means a small market franchise like the Oakland A’s could get envision themselves in a bidding process that it would normally have no right getting into since they’d essentially be paying Lackey – a guy with a 6-5 record and 3.03 ERA in the postseason – around $5.5 million for a year-plus of service. The Mets? Twins? Giants? Tigers? Brewers? Braves? Name any team in contention, and it’s a possible landing spot for Lackey, which is going to make the asking price an intriguing development the closer we get to July.
Lester is a bit of a different story, though teams may look at his 3-0 record with a 0.43 ERA in three career World Series starts and realize that talent may be better suited for their needs rather than sitting on a dock fishing somewhere in October. Most competitors will be scared off by his impending free agency, but that doesn’t mean by any stretch there won’t be a market for him. See: Andersen, Larry.
You only have to go back as recently as 2008 to recall that the Milwaukee Brewers ended up dealing its top prospect, Matt LaPorta, and three other prospects, including Michael Brantley, to the Cleveland Indians for CC Sabathia, who was five months from free agency. LaPorta ended up being a bust and is currently middling in the Mexican League. Brantley (.867 OPS in 2014) is the only player involved in the deal still sticking on the Indians’ major league roster, and is an outfielder the caliber of which the Red Sox would drool over right about now.
Well, look who’s back in the hunt in the NL Central. Adding Lester might help improve a Milwaukee playoff rotation that is currently anchored by Kyle Lohse, Yovani Gallardo, and Matt Garza. Just a bit.
Lester is 6-4 in his free agent season, with a 3.15 ERA over eight quality starts. His 95 strikeouts are fourth in all of baseball behind David Price, Steven Strausburg (101 each), and Cleveland’s Corey Kluber (99). But let’s not kid ourselves; it’s the playoff resume (6-4, 2.11 ERA) teams would be trading for.
In return, the Red Sox aren’t likely to get a Bagwellian piece back, but they’ll have at least something they can file into the positives of a lost season, with the same opportunity to bid for Lester’s services come November. Or not, if they so choose.
The fact that Jon Lester is going to receive a $100 million contract from some team should be a frightening proposal. He’ll be 31 by the time he throws a pitch in year one of any deal, and history hasn’t been kind to long-term deals for pitchers over the age of 30. Cliff Lee was 31 when he signed his five-year, $120 million contract with the Phillies, and though he’s been good-to-great in the four years since, the Phillies are strapped and in last place in the NL East. Sabathia is 33, has a 5.28 ERA, and has three more years and $73 million more coming to him from the Yankees. Cole Hamels signed a $144 million contract with the Phillies in 2010. He’s 9-17 since the start of 2013.
Lester has never won a Cy Young Award. He’s never finished higher than fourth in the league in ERA. He’s won more than 15 games only once.
He’s still going to get the cash based on his consistency and what he means to a team. (Lester’s 2.5 WAR is fourth among pitchers this season, behind only Felix Hernandez, Kluber, and Yu Darvish). It might even come from Boston.
But he soon may be of no use here, other than maintaining the reason why he should be considered at the front of the line come free agency. Let him do it for someone else and chase another ring in the process if it comes to that.
Lester gets the ball Saturday in Detroit. Maybe he or Lackey will be pitching there again in a little more than a month for the home team. Maybe it will be elsewhere.
If the Sox keep losing, one will certainly be gone, and then it will only make sense to explore what else might be out there for the other. The reality seems that the situation is inevitable.

Loading Comments...