Ben Cherington as New Boston Red Sox GM: 5 Free Agents He Will Target

Ben Cherington is both the luckiest and unluckiest man alive right now.

He's just been handed the big $400 million lottery check and he gets to spend the money on anything he wants. 

Need $150 million for starting pitching? No problem.

Need $300 million for a certain superstar slugger?  We got that.

Being the GM of a team like Boston has certain challenges; money isn't one of them.

Cherington will be desperate to distinguish himself from Theo Epstein and will be working quickly to make a signature move for the 2012 season.

This is where the unlucky part of the equation comes into play.

Every move Cherington makes is going to be scrutinized and compared to the great Theo Epstein.  The man who brought Boston two World Series championships.

What if he gives Albert Pujols 10 years and $300 million and Pujols turns into post-Seattle Ken Griffey Jr.?

Something like that will define Cherington's entire career as a GM.

Let's take a look at five players that I think he'll target this offseason.

5. C.J. Wilson: SP, Texas Rangers

C.J. Wilson is going to be on every team's wish list, but only a select few will have the money to pay for him.

Wilson has turned in a remarkable 31-15 record in his first two full seasons as a starting pitcher.  He ranks in the top 10 of several important pitching categories including ERA (seventh), wins (fourth), strikeouts per nine innings (ninth), hits per nine innings (eighth), strikeouts (sixth) and games started (first).

His only downside is that he turns 31 in November, and teams could have trouble spending over $100 million dollars on a player with only two good seasons under his belt already in his 30s.

However, the Red Sox are in desperate need for quality starting pitching and will be major players in the C.J. Wilson market.

4. CC Sabathia: SP, New York Yankees

What better way to win over the Red Sox fanbase than to steal the star starting pitcher of their hated rival?

Sabathia has been a dominant pitcher since he came into the league in 2001.  He's won 59 games over the past three years and doesn't show any signs of slowing down.

Expect to see lots of Sabathia and Red Sox talk in the headlines throughout the winter.  Sabathia's agent will undoubtedly try to get the Red Sox in the bidding process to at least drive up the price the Yankees will have to pay to retain him.

If Cherington can bring in Wilson and Sabathia to team with Beckett and Lester, then the Red Sox will undoubtedly have one the best rotations in baseball.

3. Jose Reyes: SS, New York Mets

Boston's offense was one of the best in baseball last year.  They ranked high in nearly every way to measure a team's offensive productivity.

Their only weaknesses are shortstop and right field.

Jose Reyes is one of the best shortstops in baseball, and his exciting style of play is likely to make him a fan favorite in Boston.

The Red Sox would surely have to commit over $100 million to bring Reyes to Boston, but it would be money well-spent.

Any lineup that contains Reyes, Carl Crawford and Jacoby Ellsbury would be absolutely lethal both from hitting and baserunning perspective.

2. Jonathan Papelbon: RP, Boston Red Sox

Sometimes it's just about appreciating what you currently have instead of focusing on the things you don't.

Papelbon has been one of the top closers in baseball for several years and he posted another sub-1 WHIP in 2011.

His SO/BB ratio was the best it's been since 2008, and he's sure to draw interest from any team that can afford a large four-year contract for a closer.

Boston is one of those teams, and while Daniel Bard has emerged as a viable alternative in the closer role, I would still expect Cherington to approach Papelbon in the offseason as well.

1. Albert Pujols 1B, St. Louis Cardinals

Pujols is going to get 10 years and $300 million dollars from someone.  This is going to happen.

However, there are only three to five teams in all of baseball who are going to be willing to spend that much money.

Lucky for Cherington, Boston is one of them.

The departure of David Ortiz means there is a hole at the DH spot that Pujols and Gonzalez could rotate between.

The draw for Pujols would be the ability to bat cleanup in one of the best lineups in baseball, and the fact that he could add extra years to his career by playing DH.

It's going to be difficult to get Pujols to leave St. Louis, but Boston will undoubtedly be in the mix.