Rocket's Re-Entry: Where Will Roger Clemens Land?

"...Sometime during the month of May, but certainly, not very soon."

That's Roger Clemens' agent talking about when the Rocket will make a decision about his future. Clemens has been working out and is still weighing his options, which include Houston, Boston and New York.

The million-dollar question: Where will he wind up?

May 31st—that's the date Clemens signed with Houston last year for an absurd $22 million. Although he only saw a portion of that (around $12 million), he still commands a lot of cash.

That said, May is going to be a huge month for the three teams in the Clemens sweepstakes, as well for Clemens himself.

This month will give everyone a a better feel as to where each club is headed. The Yankees will hope to get healthy, the NL Central could start to clear up (doubtful), and Boston may be able to identify a handful of problems that need fixing.

Here's my breakdown of the Rocket's suitors:

Why Clemens will sign: Houston is home for Clemens. He has everything to go back to—including his son Koby, who plays for the Class A Lexington Legends. Houston is also where Clemens will be given the opportunity to stay home when the team goes on road trips. Who wouldn't want that? I think every pitcher would love to stay home on road trips and rest.

Looking at the division, the Astros should be in the race all season for the title. The only problem is that most of the division will be in the race all season, as seems to be the case every year in the NL Central. Right now the Brewers (!) are sitting atop the standings, and there isn't a team that you can expect to flex its muscles and win the title going away.

Clemens can come in and team with Roy Oswalt to be a rather dominant 1-2 punch for the Astros. More importantly, Clemens likes it in Houston. It's probably the most comfortable place for him at this point. There won't be the same amount of media attention as in New York or Boston. He can pitch for a good team—and do it in the comfort of his own home. 

Why Clemens won't sign: It's not Boston or New York.

The Astros won't win a World Series this year. They just don't have the pieces to contend with the other teams in the league.

 
If Clemens is going to come back and pitch, why would he pitch for a team that won't win it all? He's too intense and driven to expend all that time and energy for a mere chance at a playoff berth. 

Boston Red Sox
Current Record: 16-9
GB: -- (1st place AL East; 3.5 games ahead of Toronto)
 

Why Clemens will sign: Boston is the team he came into the league with, and he'll wear a Red Sox cap when he's inducted into the Hall of Fame. To return to Fenway would bring everything full circle for Clemens, and would, I'm sure, be very enjoyable for him.

Moving past the sentimental reasons, he would join what would become a phenomenal pitching staff. The Sox already boast Daisuke Matsuzaka, Josh Becket, Curt Schilling, and up-and-down starters in Tim Wakefield and Julian Tavarez. Their closer, Jonathan Papelbon, looks pretty much unhittable. And now Hideki Okajima (the best Japanese pitcher on their roster at the moment) has come out of nowhere to pitch well.

Why would Clemens not want to be on that staff come summer time? Couple his arrival with (most likely) Jon Lester's, and the Red Sox starters would feature Clemens, Schilling, Becket, Matsuzaka, and Lester. That leaves Wakefield and Tavarez to work on odd days or out of the bullpen.

Add the fact that the Red Sox can hit, and Clemens could be walking into a situation where it's World Series or bust.  And as I said earlier, it seems like that would be the only reason why someone like Clemens would want to come back.

It's even possible the Red Sox might be able to get away with letting Clemens stay home on road trips. I mean, think about it: With so many starters, it seems like the Red Sox would have enough arms to allow Clemens to stay in Boston (or fly to Houston) when the team is out of town for an extended period. 

1. If the Red Sox don't allow Clemens certain perks, he might pass.

2. A bigger one—who on the Red Sox is Clemens friends with? There isn't anyone who you could imagine Clemens calling on a weekday to play a round of golf. This doesn't seem like a big issue to some, but to me, it is one of the big reasons why he might sign with...

He's friends with a lot of the guys on the team, and at least has a positive relationship with most of them. The Andy Pettite connection is obvious, but Clemens is one of the reasons Jason Giambi is in New York. Giambi is even constantly texting Clemens to "hurry up."

Clemens also enjoyed a lot of success in New York, winning two World Series rings in 1999 and 2000. You've got to believe that every Yankee fan would welcome him with open arms.

Although the team is struggling, Clemens could join a formidable starting rotation of Mussina, Pettite, and Wang. Adding Clemens to those three would make for a lethal front four.

Plus, Clemens can think to himself, "I can save their season. And if—when—I do save their season and win a Word Series, they'll love me and I can finally retire." 

For a gamer like Clemens, that type of thought might be the ultimate incentive.

If the Yankees continue to struggle, they will be forced to do something drastic to salvage their 2007 World Series ambitions—and offering Clemens an absurd amount of money along with anything else he wants might be just the thing.

Why Clemens will not sign: I'm not sure the Yankees are ready to offer the perks that Houston will. I don't see them allowing Clemens to stay home on road trips—not given how thin their pitching staff is (as I write this, Phil Hughes just left the Texas game with a hamstring injury).

The big thing will be whether the Yankees are still struggling and having injury problems in late May—and, at the same time, whether the Red Sox are still cruising along. If the Boston situation seems more likely to yield a championship, I don't see why Clemens would go to New York.

I really think that the only way Clemens doesn't sign with New York is if the Yankees put together another miserable May and it scares Clemens into thinking that they don't have a chance at the World Series.

Something else to think about: What if Clemens isn't effective? This month of work is going to be big—not only for the teams involved, but also for Clemens himself. He turns 45 in August, and if his body breaks down in workouts or shows signs that he can't compete at a high level, he'll retire. That said, such a scenario is highly unlikely.

 

Either way, I don't see Clemens returning to Houston. It's all about the World Series ring for him, so it really it comes down to Boston or New York. And is that really surprising to anyone?

 

My prediction? I'm going to go with New York. I figure they're going to break the bank for him, and Boston won't want to match. If they're paying Andy Pettite $16M for one year, what would the ceiling be for Clemens?

The Yankees' win-at-all-costs philosophy makes me believe we'll see the Rocket back in pinstripes before the end of the summer.