The Yankees, Cliff Lee & Roy Oswalt

What do the Yankees, Cliff Lee & Roy Oswalt all have in common?

I'll give you a hint:
- The richest organization in sports, dedicated to winning.
- 2008 Cy Young award winner, dominated Yankees in the World Series, has a 2.88 ERA in 2010.
- Ace of the Houston Astros, back to back 20 game winner, requesting a trade to a contender.

Give up?

All three have been linked this year in trade rumors.

We'll begin with Roy Oswalt, the Houston Astros ace who this year requested to be traded. Oswalt won 20 games back to back in 2005 and 2005 and led the Astros to the '05 World Series. Often looked at as one of the game's most underrated pitchers, the righty Oswalt has not recieved much publicity due to the poor play of the Houston Astros throughout his career. After recent losing seasons, Oswalt has become fed up with losing and requested a trade this year to a contender. The usual suspects have been thrown out: the Yankees, Red Sox, Mets, Dodgers, Braves, Phillies and Angels. However, the only team with enough money to afford Oswalt is the Evil Empire that is the New York Yankees. Oswalt, 32, is making $15 million this season and has an option of $16 million for 2011 which his club can decline or pick up depending on how he pitches. Perhaps the one deciding issue here besides the money is Oswalt's age. 32 is beyond the prime of a pitcher's career. It is at this time that a pitcher begins to break down and lose speed and effectiveness of his pitches. The other factor: Oswalt has pitched in the weak National League Central his entire career. Why is this a problem? The NL has always been described as the weaker of the two leagues, seeing as pitchers technically only face seven batters, the eighth being the weakest position player and the ninth being the pitcher's spot. Many wonder how a NL pitcher could transfer to the American League, especially in this case, perhaps baseball's strongest division, the AL East. Having the face the Red Sox, Blue Jays, and Rays most of the time could be a challenge.

Is there a chance Oswalt comes to New York by July 31st? Yes, of course, but is it likely? No. I think Oswalt will end up in New York, but with the Mets. First of all, he's 4-8 this year wit ha 3.16 ERA. Oswalt's been quoted as saying he wants to play here but I highly doubt that the Yankees would be willing to take on Oswalt's $15 million this year and next year when they already have a sturdy 5 man rotation. I only see this happening if they trade Javier Vazquez, which is unlikely, seeing how well he has pitched lately (5-2, 2.93). As well, it appears as though the Astros are reluctant to trade Oswalt and would require a "King's ransom" to trade him. Yankee fans know what this means: Jesus Montero. The Astros would most likely ask for a package around the #4 best prospect in baseball to which the Yankees would bluff. I doubt that Yankees would make this trade, especially with our other pitcher in this discussion...

Enter the lefty, Cliff Lee.

Since being traded to the Seattle Mariners this off season in the 3-team trade that sent Roy Halladay to Philadelphia, Lee, 31, has done nothing but dominate. This year the free-agent-to-be is 4-3 with a 2.88 ERA for a terrible Mariners team. After dominating the Yankees for the Phillies in last year's fall classic, you can't think that the Yanks didn't take notice. This week, the Yankees have been reported as connected to the 2008 Cy Young award winning Lee, and it seems as though they would like to trade for him. Like Oswalt, the usual suspects: the Yankees, Mets, Red Sox, Dodgers, Braves, Phillies and Angels have been linked. The Mariners, reportedly, have been scouting the Yankees farm system in order to try to build a package that they would want for Lee. The package reportedly would include SS Eduardo Nunez as well as either of the catching prospects Jesus Montero or Austin Romine. In order for this to happen the Yankees would have to be assured that they get at least a 72 hour window to try to sign Lee to an extension before free agency.

But the question has been asked: Why would the Yankees trade top prospects for Lee when he is a free agent come this fall and can be had for money and sacrificing the future? Lee has been quoted as saying that he wants to test free agency, and c'mon, he knows the Yanks would offer him the most cash. So why would the Yankees trade top prospects for him and then lose him as a free agent rather than sign him? It makes no sense whatsoever. Apparently though, the Yankees have been scouting Lee, leading to speculation that a trade could be in the works. I doubt it happens though, I believe the Yanks are going to sign Lee in the fall rather than trade for him. To me, I think that's best for the organization's future and would prevent fans from ripping the Yankees for the move.

Of course, either of Oswalt or Lee could end up with New York's other team: The Mets. They've been interested in both of the elite pitchers, but analysts are skeptical of the amount of money the Mets have (to sign one to an extension), and the quality of the prospects they could trade. The Mets have one of baseball's worst farm systems, even the prospects they used in acquiring Johan Santana weren't great, and they'd become even worse if they traded top prospects Jenry Mejia, Reuben Tejada and Reese Havens for Lee or Oswalt.

So, gun to my head who do I think the Yankees trade for?
Cliff Lee.
It makes more sense than Oswalt. He's cheaper, younger, and he's dominating the AL. A move for Lee would make much more sense for the Yankees. I'd rather not give up Jesus Montero, the #4 prospect in baseball and best position player in the minors since Derek Jeter, but it's not in my hands. I believe that it's much more likely that the Yankees sign Lee as a free agent this off season.

So, gun to my head who do I think the Mets trade for?

Roy Oswalt.

He'd probably cost cheaper prospects than Lee, he's an NL pitcher, and he's already signed for this year and next year if the Mets were to pick up his $16 million option. Though giving up the prospects always hurts, I believe that the Mets could find a way to get Oswalt without giving up Mejia. If they can do that, then Mets nation would be ecstatic with a 1-2 of Santana-Oswalt.

Alas, we'll just have to wait until July when the rumor mill heats up. Who knows, either of these men could be wearing pinstripes or blue and orange come July 31st.

Only time will tell.

Brian Cashman & Jesus Montero on the right:

Cash: Jesus, how do you feel about Seattle?
Jesus: What? No, I want to play for the Jankees.

UPDATE (1:21 PM) Well, here you have it! Roy Oswalt would accept a trade to the Mets.