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I’m very glad Jim Hendry pushed himself away from the table at the winter meetings. In post-mortem remarks to Tribune reporter Phil Rogers, Hendry discussed–very refreshingly, I thought–what the impact of the trade would have been on the team three or four years out.

Hendry said he was looking beyond the 2009 team when he decided not to do this deal. He sees [Josh] Vitters as a key part of the future, as he is expected to be ready to take over at third base if Aramis Ramirez opts not to exercise his player option for 2011 or the club doesn’t exercise its option for ’12.

“The Chicago Cubs are a big-market club,” Hendry said. “But still, you have to have a flow of talent coming to allow you to operate the way you need to operate.”

This was a better perspective on the Cubs than I heard a few days ago when a Cub source was quoted (by Dave van Dyck of the Trib) as saying that the team had “a two-year window to win.” That sounded like a rationalization for trading Vitters, the key Cub piece in the Peavy deal. Vitters is nineteen years old and is conveniently outside the window, since even the most optimistic scenario would delay his rookie season until 2011.

Vitters was the #3 overall pick in the June draft of 2007. To get that pick, the Cubs had to finish last in the NL in 2006 with a 66-96 record. High picks can prove valuable, even to the Cubs, as when they drafted Mark Prior #2 overall in 2001 after finishing 65-97 the year before. Two years later, Prior won 18 games for the Cubs. Then he won two postseason games and deserved to win a third game, which would have been a big one. That team had two rotation starters who had been high Cub picks, Wood and Prior, and won six playoff games.

If Prior had not fallen to the Cubs in that draft, they would likely have drafted Joe Mauer or Mark Teixeira. When they selected Vitters, the Cubs passed over Matt Wieters, minor league player of the year in 2008 and a likely starting catcher for the Orioles in 2009. Wieters is farther along in his career because he was drafted out of college and is four years older than Vitters.

The events of recent weeks have demonstrated the bind that Hendry is in. Working nonstop and straining the batteries in his cellphone, he has made one trade, Wood for Gregg. Very few people think this deal makes the Cubs better, except in the sense that it frees up the closer spot for Marmol; but it saves Hendry $6 million. If the Cubs do sign Milton Bradley, they will have to trade Mark DeRosa to pay for him, and that won’t be enough. They must also be looking to trade Derrek Lee to San Francisco or Oakland, teams on whose behalf he might waive his no-trade clause, since he lives in nearby Sacramento. A couple of months ago I identified Lee and DeRosa as the most tradeworthy players, since they would have real value in a trade and there are cheap internal replacements for both of them.

I wonder if the team as presently constituted has much more than a one-year window. Piniella is signed for two more seasons, but I have a hard time imagining him returning in 2010 if the Cubs are three-time postseason losers after 2009. For Piniella’s sake, they don’t have to win the world series next October, but they do have to win the division series.

What happens when you drain all your resources to construct a good team that isn’t good enough? The Cubs have very little flexibility. They have players with big contracts and no-trade clauses who are underperforming, like Lee and Zambrano and probably Soriano, though I’m never sure what to expect from him. They have players who are themselves tradeable but whose contracts frighten away other teams, like Marquis and Fukudome. There may be a new owner in the wings who is pricing the Cubs based on a plan to write off some of these long-term deals and start a rebuilding process, whether major or minor.

In any case, a realistic window for Cub success should include a few of the out years when Josh Vitters will be in the lineup.

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