With the Red Sox’s tail spin over the last week, the defending World Series champions have become sellers leading up to this year’s trade deadline. General manager Ben Cherington already shipped out Jake Peavy to San Francisco and the names of several other Boston players have been floated around as potential trade possibilities. But none is bigger than Jon Lester.
The big lefty has been the ace of the Boston staff, and he is enjoying what may be the best season of his career. In 21 starts he is 10-7 with a 2.52 ERA and 149 strikeouts in 143 innings. His first half performance was good enough for him to make his third career all-star appearance.
In most years in Boston, Lester would be the horse leading the team into October. However, this is not that type of year. With the Red Sox 10.5 games back in the A.L. East and 7.5 games out of a Wild Card spot, it seems that Boston players will be spending October closer to Hole 1 than Game 1.
With Lester, this is where it gets complicated. Because his contract runs out after the year, there is no guarantee he returns to Boston, though he has repeatedly said he wants to make it his career home. The Sox’s multiple offers to him on a new contract were far below market value for a pitcher of his caliber and were subsequently turned down.
That leads us to this point. With likely no postseason to worry about, the smart baseball decision would be to move Lester to pick up some players who can help down the road. The Red Sox already, in essence, set a market for starters with their trade of Jake Peavy last week. Boston picked up two of the Giants’ top 10 prospects for a pitcher who had one win on the season.
With that in mind, the return for Lester should be significantly higher, even if he does just turn into a two-month rental. And the Red Sox seem to be operating with that in mind.
MLB Network insider Ken Rosenthal recently tweeted:
Sources: #RedSox listening on Lester but seeking huge return. #Dodgers among teams interested.
— Ken Rosenthal (@Ken_Rosenthal) July 27, 2014
And ESPN Boston reported that Matt Kemp could be part of that huge return in a Lester trade.
If Cherington does plan to trade Lester, there is no reason he should accept anything less than a top-quality package. Not only has he pitched well this year, but he comes through when it matters most. He’s been stellar in the playoffs during his career with a 6-4 record and 2.11 ERA in 13 games. He will instantly make any contender that much more of a threat down the stretch.
But it will have to come at a cost. Especially the way the market is shaping out. With the Rays seeming less likely to deal David Price and Phillies’ GM Ruben Amaro saying Cole Hamels is not available, Lester is far and away the top arm available. And in a seller’s market, he could garner a king’s ransom.
Which is why Matt Kemp makes absolutely no sense for the Red Sox. Kemp is exactly the type of player Boston has been trying to rid itself of. He is a high-priced, long-term, injury-prone potential headache. There was a time this deal would have made sense. But that was in 2011. Kemp is no longer the five-tool player who nearly won an MVP Award and made two all-star teams.
A player with his numbers is not worth a pitcher the caliber of Lester. This season, he is hitting .273/.339/.429 with eight home runs and five stolen bases. He’s also been caught stealing five times. According to Baseball Reference, he actually owns a negative WAR at -1.1. Since when is that worth a potential Game 1 playoff series starter?
And there are also character concerns with him, which is something the Red Sox don’t need. He has been in a battle for the last year over playing time in the L.A. outfield. While that would not be a problem in Boston, that opens the door for other issues down the road.
And the Red Sox will be forced into a “down the road” situation with Kemp. He is under contract through the 2019 season at $21.5 million per year. Those are the exact types of contracts Boston has been avoiding, and a package that would have most likely gotten Lester to commit to staying put. Any deal between the Red Sox and Dodgers would require L.A. to eat a large chunk of that contract.
Otherwise, it would become the exact opposite of the 2012 trade between the two teams. The Dodgers bailed the Red Sox out of a painful situation involving unhappy and under-performing players on big contracts. A Lester-for-Kemp trade would be a gift to L.A and would eventually prove to be a burden for Boston.
If the Dodgers are truly interested in Lester, which there is every reason to believe they are, it is going to have to be for more that Kemp. Cherington would love a package including top prospect Joc Pederson, but so far L.A. has not budged, instead preferring to keep him. They need to change their tune if they are serious about Lester.
If Boston holds onto Lester and loses him in free agency, the team will get a compensatory draft pick out of it, assuming he is given a qualifying offer and declines, both of which are likely. So, part of the Kemp equation is to determine whether he has more value than the 35th or so overall pick in the draft. Chances are, he doesn’t.
Any trade of Lester likely won’t come until the last 24 hours of the trade deadline. Cherington will surely hear from other teams wanting to make a deal and, if he still does work a trade with the Dodgers, he should at least be able to leverage that interest into a better package from L.A. After all, Boston already blew it once with Lester by not signing him to a long-term deal when the opportunity was there. There’s no need to blow it again by trading him away for Matt Kemp.
