Unless the return is overwhelming, Lester and Lackey should stay put

Jun 1, 2014; Boston, MA, USA; Boston Red Sox pitcher Jon Lester (31) delivers a pitch during the first inning against the Tampa Bays Rays at Fenway Park. Mandatory Credit: Greg M. Cooper-USA TODAY Sports

The trade deadline is seven weeks away. The Red Sox are currently under .500, eight games out in the AL East, and 4.5 games out for the second Wild Card.

Once again, there’s still seven weeks for this team to reverse its fortunes and start playing like a defending World Series champion. However, if they can’t shake this hangover (just like the 2011 and 2013 San Francisco Giants), it’s probably time to look at this team as a deadline seller instead of a buyer.

There are several players who could have some appeal for clubs looking to improve their lineups. Jake Peavy could shore up the back end of a contender’s rotation. Jonny Gomes provides right-handed power off the bench. If he’s healthy and productive at the deadline, Shane Victorino could have some suitors. AJ Pierzynski is a solid offensive option behind the dish and David Ross is an excellent defensive backstop (though it’s very rare to see catchers dealt during the season).

There are two other players who the Sox will probably receive more calls on, however, if they find themselves as sellers at the deadline: John Lackey and Jon Lester.

While both pitchers could have the most appeal to contending teams, the Red Sox would be wise to hold onto both unless the proposals are very overwhelming.

Let’s start with John Lackey.

Jun 2, 2014; Cleveland, OH, USA; Boston Red Sox starting pitcher John Lackey (41) delivers in the first inning against the Cleveland Indians at Progressive Field. Mandatory Credit: David Richard-USA TODAY Sports

It seems like a lifetime ago that many Sox fans were wanting the club to cut the guy loose and eat all of his remaining salary. He has since returned to being the effective number two starter he had been with the Angels thanks to the miracle of Tommy John Surgery.
Because he missed significant time (all of 2012) with an elbow injury, the Sox now hold an option for 2015 at an estimated $500,000.

With that club option being at such a low price, Lackey should have quite a bit of interest, particularly from lower-budget contenders. But Lackey is also 35 years old and will be 36 in 2015. His age will be a red flag for suitors in regards to giving up premium prospects.

But given the Sox have quite a valuable commodity in Lackey, they should take nothing less than a package that features 1)  a near major league-ready starting pitcher who profiles as a number one or number two starter and 2) a young five-tool outfielder who’s at the upper levels of the minors.

Such an asking price would likely turn suitors away. But there’s nothing wrong with that. At the very least, the Sox have a number two starter returning for 2015 at such a low rate. There’s also a chance that both sides work out a new deal that could keep Lackey in Boston for 2016 as well.

Bottom line on Lackey: Unless the Sox can get a package featuring the pieces I just mentioned, he should remain with the Red Sox at his club-friendly price.

Now let’s move onto Jon Lester.

Ben Cherington has recently stated that the club isn’t even thinking about dealing Lester. That either means Lester is staying put or if a team wants him, they better be willing to spend heavily to acquire him.

Lester has been very good this season. He’s stated his desire to remain in Boston and the club has expressed a mutual interest in continuing the relationship (despite the first extension offer being somewhat underwhelming). If Lester is not extended, he will be a free agent after the season where he should find a very lucrative deal.

With a reputation as an effective and durable workhorse in the regular season, plus an excellent postseason resume, Lester could be a very appealing option for a contender.

But the Sox better be asking for a blockbuster in return. A good starting bid would be a package featuring all of the following: 1) a near major league-ready starting pitching prospect who profiles as an ace 2) a near major-league ready power-hitting outfielder (preferably one who bats from the right side) 3) a Double-A or Triple-A pitching prospect who profiles as a number two or number three starter and/or a five-tool Double-A or Triple-A outfielder (the Sox should be willing to throw in a lottery ticket prospect like a Sean Coyle to acquire both pieces).

With MLB’s new collective bargaining agreement, traded players are not eligible to receive qualifying offers after the season is over. Because of this, deadline buyers haven’t been willing to spend as much on rentals anymore. Despite this, the Sox should absolutely not lower the asking prices. Lackey still has value for this club beyond this season. There’s also still a very good chance that Lester does sign an extension. If he doesn’t, the club can acquire a draft pick and use the money on another free agent starter.

Bottom line, unless the returns significantly outweigh the benefits of retaining either or both pitchers, Jon Lester and John Lackey should stay put.