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Bad Contract Swap Meet


Recently, the great Joe Posnanski made a list of his 10 worst contracts and as you might expect, the Red Sox made the list, twice. Posnanski put the contracts for John Lackey and Carl Crawford in his top ten, citing Lackey’s precipitous decline and his feeling that Crawford is overrated.

While Crawford’s 2011 season has given many people cause for concern, the Red Sox also have many good reasons to expect the left fielder to rebound.  His age, athleticism, and defensive abilities all make him less of a long term risk than many other players. Many players have struggled in their first season with a new team and returned to being the players they were signed the next. Carlos Beltran’s miserable 2005 was followed by a fantastic 2006 which nearly saw the Mets make the World Series, Curtis Granderson struggled in 2010 and was an MVP caliber player this year. How about J.D. Drew, who could easily have made the 2007 version of such a list and yet still managed to be a valuable asset to the Sox for four more seasons. Crawford has been an above average hitter and elite defender in five of the past seven seasons. In both 2008 and 2011, he struggled with injuries and the inability to get on base. With the first nightmare season behind him, Crawford can take his name off any bad contract with a return to his 2010 form.

John Lackey, however, is clearly a player in decline. In two seasons with Boston he has posted a swinging strike rate well below his pre-Sox levels. While he has not lost any velocity, he has seen his fastball go from a plus pitch to a very average one. His curve is no longer effective as well and he has come to rely heavily on his slider, currently his only effective pitch. John Lackey has a disturbing 3 years/$45.75M  remaining on his contract. Whatever you make of his attitude on the mound, his personal struggles or the issues in the clubhouse, the problem with John Lackey is his deteriorating stuff. If he was a foul-mouthed, fried chicken gobbling, drunkard with a 3.45 FIP and a 2.01 ERA we would all learn to live with it. Should he henceforth be the very model of a modern major leaguer and yet still continue still to see his strikeout rate erode, all the good will and brotherly love on earth won’t make him an asset to this team. John Lackey needs to go.


The only real chance to move a contract like Lackey’s would be to take on another team’s bad deal. Fortunately, there are no shortages of bad deals in baseball these days. The Red Sox have one advantage in that Lackey is a pitcher and everyone always needs pitching. In fact, the Red Sox need pitching and trading a starter is not the way to go about getting it, traditionally. There are also surprisingly few bad contracts for pitchers out there. Swapping Lackey for Barry Zito doesn’t make much sense. The Sox likely would have to send cash or players to Houston to turn Lackey into Wandy Rodriquez and even then, they’d only get Wandy Rodriquez. If the Sox want to take a chance by swapping one bad deal for another, they would likely acquire a position player for John Lackey.

With that in mind, let’s look at a few deals that Boston might be able to swing.

The Obvious Passes:

Vernon Wells, 3 years/ $63M: Yes that’s right for a mere $21M a year you could have the worst player in all of baseball.

Alex Rios 4 years/$49.5M: The poor man’s Vernon Wells (wherein the poor man still has $49.5M to throw away)

Ryan Howard, 5 years/$125M: If the Red Sox were looking for a player with David Ortiz’s skill set, 2 years/$25M for the actual David Ortiz would make more sense, and that is a pretty generous deal. With the other $100M we could almost pay the two guys above to keep playing against us. 

Adam Dunn, 3 years/$44M: The White Sox are in trouble. Dunn had the same skill set as Ortiz and Howard but now he has none. He could recover and once again be an imposing slugger, but he was ungodly bad last season, I mean, he was Vernon Wells bad. You just don’t come back from that.

Alfonso Soriano, 3 years/$44M: Nice try, Theo. 

Jayson Werth, 6 years/$112M: Werth might actually be a good fit for Boston- he hits right handed, plays right field and can get on base, but this deal is just too much money, if it was even close to reasonable, the Sox might have signed Werth instead of Crawford. Also, considering the team has Josh Reddick and Ryan Kalish, there is a very real chance Werth would become a $100M+ platoon player. Come on! 

Interesting Options:

Jason Bay, 3 years/$49M: The money matches up well here and both teams would have a chance at getting a valuable asset. The Mets would get a pitcher who struggled in the game’s toughest division coming into a very pitcher friendly ballpark and a less slugging division. Boston would be taking a big risk in hopes that Bay would be the player he was on Boston two years ago and not the player he has been in the cavernous depths of CitiField. Bay would be without a position, however, likely making him a permanent DH or worse, seeing him attempt part-time work in right. If bringing back Jason Bay meant no David Ortiz in 2012, it is hard to see it being cost effective.

Johan Santana, 2 years/$51M: It is surprising that this deal doesn’t get listed among baseball’s worst contracts more often. Santana has not pitched since 2010, but he is expected to return next season. He has a full no trade clause and an option year for 2014 that activates if he wins a Cy Young Award. Before his injury, he was still dominating despite having fallen off from his mid-decade peak. Returning to full health for 2012, Santana could very well be an ace. However, he will also be paid more for the next two years than Lackey will for the next three and he hasn’t throw a pitch in over a year. That’s a big risk and if the Mets were willing to move him, it would only make me more suspicious of his abilities.

Let’s Do This-

Chone Figgins, 3 years/$26M: Figgins was almost Vernon Wells bad last year. He was just ordinary bad the year before. It doesn’t seem reasonable to believe he will ever be the player he was in 2009. However, this deal could be great for the Sox. They would get a player who is a switch hitter with an excellent glove at third base, allowing them to DH Kevin Youkilis part time or full time, trade Youk for pitching or trade Mike Aviles or Jed Lowrie. Figgins would not be hitting in Safeco 81 games a year and that alone would make a big difference for him. His base-running and defense can help the team even if his bat continues to falter.

Lackey would be entering a situation that would greatly improve his chances for success. He would be in a division he has played in before, in spacious, pitcher-friendly park, and out of the pressure cooker environment of Boston.

Dan Uggla, 4 years/$52M: Pitching rich Atlanta has no need or desire for John Lackey and plenty of reasons to hang on to Uggla. Despite that, this is a deal Boston should at least check in on deal for Uggla. His right-handed power would play perfectly to Fenway’s Green Monster and he a move to third might help his defensive numbers, which are terrible enough that a move to DH might help even more. Atlanta could shave some money off their payroll and also grab a prospect or two in a deal like this, but really, I can’t image they would go for it.

Cents on the Dollar: Lackey could be attractive to a National League team in the playoff hunt. A team like Cincinnati, Milwaukee, San Diego or Arizona could look to bring in Lackey to sure up their rotations and send back a B level prospect or so, assuming Boston made him affordable for such teams. They should admit that John Lackey is not going to be an average pitcher in Boston and get the best return they can for him, even if that should mean playing some of his salary. The team can find better production for his roster spot and that is the bottom line.