Jake Peavy to Chicago Cubs Heats Up: Deal Sours for Cubs Fans

Either Padres GM Kevin Towers is throwing stuff at the wall praying something sticks, or Jake Peavy very well might be a Chicago Cub by the end of the Winter Meetings.

But at what cost?

The latest rumors, as have been reported by various outlets, have Towers claiming a deal to be eminent, with as many as four teams now involved. There would actually be three deals that would take place to end up with Peavy in Chicago.

Deal One: Cubs send center-field prospect Felix Pie to Baltimore for left-handed starting pitcher Garret Olson.

Olson, 25, has limited experience in the majors but apparently is a starting pitching prospect the Padres like enough that he would sweeten a deal more than anyone the Cubs have in their own system.

In return, the Orioles would receive a raw, young outfielder that appears to have run out of chances in Chicago. Whether or not he deserves this fate, or that letting Pie go this early in his career will benefit the Cubs in the long term, is yet to be seen. This deal could be done as soon as Tuesday.

Deal Two: Cubs trade veteran second baseman Mark DeRosa to Philadelphia for a package of players centering around left handed starting pitcher J.A. Happ.

Happ, 26, a graduate of Northwestern University in Evanston, IL, has even less experience in the majors than Olson. He has started nine games in his brief career, but recorded 26 strikeouts in 31.2 innings in 2008. DeRosa, meanwhile, has one year left on a contract he has outplayed during his tenure in Chicago.

He would give Philadelphia fantastic sub for Chase Utley while he rehabs from the hip surgery he's having this winter and also give Manager Charlie Manuel options with his outfield.

Deal Three: The Cubs trade Happ, Olson and...to San Diego for starter Jake Peavy.

Towers is on record as saying he wants five players for Peavy. The reason the package falls apart after Happ and Olson is because the two requisite deals strip the Cubs of what would have been the depth they had to move some specific prospects.

If DeRosa leaves, one would assume the Cubs wouldn't trade young second baseman Mike Fontenot (unless the Pie/Olson trade was a part/prelude of a Brian Roberts deal).

Another name that has been a centerpiece of trade rumors for Peavy has been young Cubs left-handed starter Sean Marshall. But in trading for Happ and Olson, the Cubs would figure to acquire two lefties to put into the deal. Would San Diego want three left-handed starting pitchers in the trade?

This leads me to believe that Marshall and Fontenot would not be part of the Peavy trade. Minor league third baseman Josh Vitters has long been suspected to be the top Cubs piece to the trade. I would tend to replace Marshall in the deal with a right-handed starter, perhaps Kevin Hart.

Hart threw well out of the Cubs bullpen last year and has a nice upside. The fifth player might be shortstop Ronny Cedeno to replace Khalil Greene in San Diego. It would certainly make sense for both sides.

So, Deal Three would end up being Vitters, Hart, Cedeno, Happ and Olson for Peavy. Or, if you look at net cost, it would be DeRosa, Pie, Cedeno, Hart, and Vitters.

I'm not sure how much of a fan I am of this deal as it's being rumored. There is no question why the World Champion Phillies are enamored by him, but the reasons the Phillies want him are the exact reasons the Cubs should want to keep him. DeRosa was arguably the Cubs' most valuable player in 2008, starting at third, second, right field, and shortstop.

To insert Fontenot into an everyday lineup as it's currently comprised weakens the lower middle of the order. Fontenot, referred to by Ron Santo as "Baby Babe Ruth," has shown flashes of power but in limited experience. To bank on him for 162 games on an aging roster with one, maybe two good years left is a huge gamble.

The wild card in the mix is Hendry moving fifth starter Jason Marquis. This needs to happen for three reasons: Marquis' salary ($9.875 million in 2009) needs to be off the books to make room for Peavy's larger deal, Marquis needs to vacate his position in the rotation for Peavy, and he made it clear last March he won't go to the bullpen, and the third and final reason Marquis needs to leave is because he isn't that good to start with.

There has been speculation that Marquis may head to Kansas City, perhaps for the left-handed-hitting right fielder the Cubs want (David DeJesus? Mark Teahen?). There have also been rumors that Marquis has been courted by the Mets, who raised their offer to Francisco Rodriguez to three years, $37 million and might have the closer signed by the end of Tuesday.

I would advocate a third team, with Marquis heading to South Florida for Jeremy Hermida of the Marlins.

If the Cubs do move Marquis, DeRosa, Pie, and a few prospects and end up with Jake Peavy and a mediocre right fielder in return, I would count this winter at a loss for the Cubs. Hermida would be a nice fit on the North Side, but he's still young. So are DeJesus and Teahen.

Perhaps Hendry is looking down the Red Line at Kenny Williams, stockpiling talent while unloading overpaid veterans, and he's developing a false sense of trigger happiness. While a starting rotation of Peavy, Carlos Zambrano, Rich Harden, Ted Lilly, and Ryan Dempster might be the best in all of baseball, it won't mean a thing unless the Cubs win.

101 years and counting...let the fun begin.