The Cubs' dead deadline

Deadline season has swung into action, and we're already sorting out winners and losers. But on the running scoreboard of who did what over the next 70-80 hours, there's going to be another tally -- a list of teams that didn't even enter the sweepstakes. Which team is likely to be found in the front rank of these wallflowers? Odds are, it'll be the Chicago Cubs, baseball's worst balancing act between payroll and performance.

The Cubs' situation isn't a recent development. The Cubs have been shelling out around $130 million for each of the last three seasons without winning anything. What might be particularly galling is that they've been paying more than they did for their division-winning teams in 2007 and 2008. That's not too surprising a development -- between the backloading that tends to be normal with multiyear commitments to veterans and the inevitable (and overdue) raises younger players like Carlos Marmol and Geovany Soto got via arbitration eligibility, seeing payroll go up might have seemed inevitable.

It wasn't inevitable, though. Payroll expanded because Jim Hendry chose to spend the money, and he had the authority to make it so. With an ownership situation that was in transition and a veteran skipper in Lou Piniella who wanted to win now, it wasn't like Hendry had a shortage of enablers after 2008, when he retained veteran Ryan Dempster (four years, $52 million) and added the brief drama of Milton Bradley (three years and $30 million). These were expenses added on top of the already massive investments and the multiyear extensions made in Carlos Zambrano, Aramis Ramirez, Alfonso Soriano and Kosuke Fukudome.

Pay for greatness, and great paychecks are no problem. That isn't what the Cubs have gotten, however, and that's why the Cubs are stuck now -- not because of what Jim Hendry isn't doing now, but because of what he did back in the salad days, back before things started falling apart in 2009. The problem is not a failure to notice that the window for that team has shut, it's that there's very little to be done because of these commitments. The Cubs might have thought these deals would buy them a third bite at the postseason apple, but instead they guaranteed their present misery, 20 games under .500.

Not all of Hendry's deals were bad. Derrek Lee delivered value over most of his five-year, $65 million deal, but it was signed after Lee was already 30, and that's another element of the Cubs' paralysis -- picking the wrong players to grow old with. Fukudome turned 31 shortly after he debuted as a Cub; Marlon Byrd was already 32. Soriano turned 31 shortly before he arrived in Wrigley, signing after a 4.1 WAR season with the Nats; he has never matched that in any season as a Cub, and he almost certainly never will. Dempster was in his age-32 season in the first year of his new deal, awarded after a 5.3 WAR campaign in '08. He barely matched that in his next two seasons combined.

Multiyear extensions to A-Ram and Zambrano seemed to make more sense. A-Ram's came after his age-27 season. He had given the Cubs two seasons with WAR marks over 4.0 before the disappointments of the last three seasons. Zambrano got his extension when he was 26, after four straight seasons delivering WARs over 4.0, but he has yet to deliver another.

So the Cubs are cooked, but that was locked in long ago. The extra bit of agony involved goes beyond the expense of assembling this team. Because of Hendry's added-on sweeteners to so many of these deals, the Cubs won't even get the slender benefits of a deadline teardown, no matter how much disgruntled fans might want one. Hendry's generosity in surrendering no-trade clauses handicapped the already-difficult task of trading away any of the eight-figure elephants on the roster. Zambrano, Fukudome and Soriano have full no-trades, while Ramirez's 2011 window is effectively nailed shut by a trade guaranteeing his 2012 option. And any contender willing to rent Ryan Dempster for the stretch probably doesn't want to take on his $14 million player option for next year.

Failure this expensive and this comprehensive only gets bailed out on Wall Street, so Hendry's likely passivity at the deadline this year shouldn't be cause for any particular surprise or anguish. The virtues of employing any of these guys is far from a slam-dunk for the buyer, guaranteeing that even if Hendry miraculously dealt any of them, the most the Cubs would get would be a little salary relief and perhaps an organizational player. Expensive and bad players aren't worth much in trade -- add the difficulty in getting any of them moved, and you can't really bang on Hendry for what he can't achieve -- he created this problem three to five years ago.

Christina Kahrl covers baseball for ESPN.com. You can follow her on Twitter.