Could The Chicago Cubs Pursue Roy Halladay?

I was wandering around various baseball sites today, and came across a thought that honestly made me laugh when I first read it.

"[The Cubs] have the finances... have a chance to win, which is what [Roy] Halladay will certainly require, and while the Cubs' farm system isn't atop the league right now, there are a few intriguing talents that could fill out a package for Halladay."

That's on ESPN.com's Rumor Mill. I've read a couple other places that the Cubs might be a "darkhorse" candidate to make a splash for the Blue Jays' ace.

Wow. And I thought the only rumors "coming out of left field" this winter for the Cubs would be Alfonso Soriano taking pitches next year!

But after some reflection, there might be a possibility that the Cubs could, and might be more willing to, put together a package of players that's both larger and better than a team like the Phillies, that doesn't necessarily need Halladay to win.

In the final year of Derrek Lee and Ted Lilly's contracts, and with questions swirling around GM Jim Hendry's future with the club past 2010, the Cubs' sense of urgency should be like needing a bathroom on a stalled elevator.

But what could the Cubs offer Toronto that would make them consider moving the former Cy Young Award winner?

Josh Vitters , 3B

Vitters is one of the top two or three prospects in the Cubs' organization, and has been the headline generating trade piece for the Cubs over the past 15 months. Right now, the Blue Jays have former Cincinnati third baseman Edwin Encarnacion, whom they acquired for Scott Rolen in a mid-season trade, working the hot corner.

Vitters would present an opportunity for the Jays to see what they have in Encarnacion for another year or two before the think about bringing up the big-swinging Vitters.

However, the one question mark here would be whether or not Vitters' defensive issues raise red flags (bad Canada pun?) about his transition onto the carpet in Toronto. If he projects more as a corner outfielder, that might hurt his value.

Starlin Castro/Ryan Theriot , SS

Castro might be the biggest intrigue of the Cubs' winter. He's a 19-year old shortstop who's been arguably the best player in Arizona this fall, and projects as a significantly better major league shortstop than the current resident on the left side of the Cubs' infield, Theriot.

I personally doubt the Jays would want Theriot, having already lived through a failed David Eckstein experiment in the last few years. He is a good gap hitter, though, and his minimal salary and ability to contribute at the major league level now might make him a candidate for the deal.

The Jays could use a middle infielder to play next to Aaron Hill, and one of these two could be a part of a package.

Geovany Soto , C

This might be a long shot, but Soto showed enough potential in his 2008 Rookie of the Year season that Toronto might be intrigued. They are currently working with Raul Chavez behind the plate, so Soto might become a more offensive option if he can bounce back from his high winter, and low season of 2009.

Esmailin Caridad/Jay Jackson/Andrew Cashner/Jeff Samardzija , RHP

Caridad was effective in a brief run with the Cubs at the end of 2009, and might factor into their bullpen moving forward. He's still raw and has great stuff, but much like Carlos Marmol, he doesn't always appear to know where the ball is going when it leaves his hand.

Samardzija wants to be a starter, but hasn't shown a big (or good) enough repertoire at the major league level to be effective yet. He might get the chance to start in Toronto, though, which might make him think twice about his no-trade clause.

Jackson and Cashner haven't seen Wrigley Field yet, but both have had solid minor league careers. Either could swing between the bullpen or rotation, and would at least give the Jays enough organizational depth to potentially make other moves in the future.

Jake Fox , 3B/OF/DH

Fox is a fascinating player for a potential deal with Toronto because of his skill set: He can hit. The Cubs haven't found a position in the field where they feel confident in Fox, but his ability to play a corner outfield spot, or third base, or even perhaps first base, and DH when needed, might make him valuable.

In 2009, Fox hit 11 home runs in only 209 at bats. If he got a chance to bat every day, whether he played in the field or not, might show that he's a legit 30-homer guy. Or, he might just be the second coming of Matt Stairs. Either way, at $400,000, he's cheap and can hit at the major league level. The Jays could be interested in Fox.

Carlos Marmol , CL

Here's the great wild card in any Cubs rumor mill this winter. Marmol would be a substantial upgrade over Jason Frasor in Toronto, so there would have to be interest in a young arm that's still in arbitration years.

Where this becomes intriguing on the Cubs end is factoring in the deep field of available closers this winter. It would require the Cubs to spend more money, but they could certainly bring in a veteran closer with historically better control than Marmol.

However, if the Cubs put together a package, the addition of a pitcher the caliber of Halladay would be incredible. Putting a bonafide innings eater in front of Carlos Zambrano and Lilly, who played with Halladay in Toronto, would give the Cubs arguably the strongest rotation in the National League.

It would also greatly reduce the Cubs dependency on their bullpen. Halladay averaged 7.2 innings per start last year, with nine complete games; by comparison, the Cubs had one complete game as a team last year.

Whether or not the Cubs would want to part ways with the substantial package of prospects and potentially major league players it would take to get Halladay, with only one year left on his contract, is another huge question.

Last year, the Cubs made a now-infamously public attempt to get Jake Peavy away from San Diego and failed. Whether or not the Cubs are as open about any major player movements in the future is questionable after Hendry had egg on his face after not getting Peavy.

Oh, did I mention Peavy's now pitching in Chicago after all... for the White Sox?

But if Hendry's truly going for broke in 2010, mortgaging a few prospects that might, or might not, do anything in the majors for a legit front-of-the-rotation starter might be the bold move it takes to get the Cubs back into October.

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