Let’s assume for a minute that Theo Epstein remains the general manager of the Boston Red Sox. What would you want him to do to fix the mess that is the team’s clubhouse at this point? Some say simply a new manager to lead this group is needed, but I see a much bigger need to get some new blood in the organization.

Where should Epstein start? That’s debatable, but I think it has to begin with one of the most difficult tasks, which would be to trade John Lackey.

Lackey has proven to be a huge bust for the Red Sox. Even if he wasn’t signed for big bucks over long years, no one could say he’s been even close to a decent pitcher for this staff. He got a gift 12 wins this year, mostly due to the fact that most of the season the team was tearing the cover off the ball. At 32 years of age, he’s no spring chicken, but he still could hold some value to clubs, specifically National League teams, who are looking for some rotation help. While some spots would require the Red Sox to eat a significant amount of his salary – which they’ve been known to do – there are some places that may be willing to trade one large contract that hasn’t worked out for another.

Here’s a look at some possible suitors fitting that description.

New York Mets and Jason Bay (Two years, plus vesting option remaining on a four-year, $66 million contract)
Bay has been hurt for a significant amount of time since signing a huge contract after the 2009 season saw him traded to the Red Sox. He’s also had a lot of his power sapped by playing in the canyon that is more commonly known as Citi Field.
The Mets need pitching help, as they were forced to rely on the likes of Dillon Gee, Mike Pelfrey and R.A. Dickey this past season. A pitcher like Lackey who has always given up his fair share of hits is much better suited for a park like Citi Field and most of the time pitchers have an easier time getting away with average stuff in the National League than the American League East.
As for what the Red Sox would be getting, it would be a gamble, but Bay did post a .915 OPS in 200 games with Boston not all that long ago and would not be relied on as the centerpiece of the team’s offense. His arrival would also mean a move for Carl Crawford away from the Green Monster, which he played horribly.

New York Mets and Johan Santana ($24 million in 2012, $25 million in 2013, $25 million team option that becomes vesting if Cy Young and innings pitched criteria are met with a $5.5 million buyout)
Santana’s problems have been the exact opposite of Lackey’s – still has the stuff, but can’t stay on the field. Santana didn’t pitch at all in 2011, making him a huge gamble for the Red Sox if they were to go this route. However, at the same time, Lackey is a big gamble for New York. After being a horse for most of his career, Santana may be breaking down and if the New York medical staff isn’t sold, this could seem like a worthwhile maneuver that could allow the team to spend the extra money elsewhere or just take the savings. Lackey could work in New York for the reasons stated above, while Santana could be a steal if he could return to form. However, his potential for a bounceback season makes this an unlikely match.

Los Angeles Angels of Anaheim and Vernon Wells (Three years remaining at $21 millon per year)
Wells was a total bust for the Angels and one of the reasons their general manager resigned last week and it’s very possible that the new general manager will want to distance himself as much as possible from the mistakes of the previous front office.
Lackey is a known commodity, which could work for the Red Sox or against them in terms of trading him back to the West Coast. Still, Lackey was always a solid competitor for the Angels and playing an unbalanced schedule against teams like Oakland and Seattle in huge ballparks could only benefit him.
His numbers as a visitor at Fenway Park have been fairly pedestrian over his career, but he’s a Yankeed killer with a career slash line of .302/.354/.517 against New York. He’s also lost a step in the outfield, so a move to left field would allow the Red Sox to move Crawford away from the wall while limiting Wells’ defensive shortcomings.

San Francisco Giants and Barry Zito ($18 millon in 2012 and $20 million in 2013, plus an $18 million option in 2014 with a $7 million buy-out)
This is probably one of the worst fits because the Giants need hitters more than they do pitching and Zito has been worse than Lackey, plus he’s injury-prone. If the Red Sox were to go this route, they most likely would end up with the record for highest salary for a left-handed specialist. Even then, he’s not a good option, as he posted better numbers against right-handed batters than lefties last season.
There’s not much reason to explore this one at all, but it at least had to be mentioned in a conversation regarding bad contracts.

Chicago White Sox and Jake Peavy ($17 million in 2012, $22 million team option with $4 million buyout in 2013)
This most likely won’t happen simply because Peavy’s at the end of his contract and the White Sox would probably just as soon eat $4 million, rather than take on Lackey’s salary and years in the hopes he can turn his career around on the South Side of Chicago. Also, if Terry Francona ends up in Chicago, odds are stacked even higher against this.
Still, Chicago may be ready to move on from Peavy, who just can’t seem to stay healthy for them. He hasn’t appeared in more than 19 games in either of his last two seasons with the team and just hasn’t panned out for a team that was a bigger mess than the Red Sox last season and could be looking to make some extreme changes.
Peavy still has good stuff, but with all the questions surrounding his health, it would be more likely the Red Sox looked into the next name on this list.

Chicago White Sox and Adam Dunn ($14 million in 2012, $15 million in 2013 and 2014)
This clearly would only happen if the Red Sox elected not to re-sign David Ortiz and given his productivity this year, that would only happen if the front office decided that he was more of the problem in the clubhouse than he was the solution.
Dunn has always been a big strikeout guy (182 in a 162 game average), but he also has big-time clout and has a career .374 OBP, which Mr. Epstein would covet and it’s hard to believe at age 31 he’s completely washed up. After all, just a year ago he hit 38 homers and drove in over 100 runs for the hapless Washington Nationals.
However, it would be a hard sell to make for the White Sox, despite Dunn’s struggles this year. It’s hard to make a case that Lackey would prove to be a strong addition unless the team loses Mark Buerhle and is looking for a veteran starter to help solidify the rotation. If there’s one thing going for Lackey, it’s that he’s durable, something that couldn’t be said for a lot of White Sox pitchers this year.

Chicago Cubs and Alfonso Soriano (Three years remaining at $18 million per year)
Soriano has always been the anti-Moneyball player and is clearly in decline. He’s a poor outfielder and has lost a great deal of the speed that made him a good tool offensively. He does still have some pop in his bat, however, and he has solid career numbers at Fenway and against the AL East.
The Cubs are in desperate need of pitching, as Ryan Dempster is a free agent and Carlos Zambrano can’t be counted on and, most likely, the Cubs will be looking to unload him, leaving the team with Randy Wells as their top starter, followed by Casey Coleman.

Houston Astros and Carlos Lee (Final year of contact, owed $18.5 Million)
This one is a stretch because Lee is on the back end of his deal and the Astros most likely would not be willing to take on more years of a massive contract unless the Red Sox were willing to eat some of the salary. That said, Houston had by far the worst pitching staff in the league and may see Lackey is a reclamation project that, if successful, could anchor a staff. Brett Myers was very shaky this year and the team’s most consistent starter, Wandy Rodriguez, is not expected to be back after the Astros tried shopping him at this year’s trade deadline. The Astros were also fooled into believing J.A. Happ was a quality pitcher.
Lee is another man on the back nine who still has enough pop that he could fill at least a part-time DH role for the Red Sox and adds an option as a right-handed bat, something the team struggled without at times. Lee crushed left-handed pitching last season at an OPS clip of 1.028 and he has a .921 OPS at Fenway Park. Should Ortiz leave, a Ryan Lavarnway/Lee platoon at DH would give the Red Sox some roster flexibility as Lee can also play first base or a corner outfield position, provided it’s for a limited amount of time, and Lavarnway, while not projecting as a full-time major league catcher, offers an option behind the plate.

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