As Jeremiah noted yesterday, the Cubs designated Carlos Marmol for assignment. This nearly marks the end of the era of Jim Hendry’s big spending, which will officially and mercifully end with the conclusion of Alfonso Soriano’s following the 2014 season. Hendry signed some petty notorious contracts over the last several years of his stint as the Cubs’ general manager. He bid against himself to sign Soriano to an eight year deal, when all reports indicate that six years would have nabbed the left fielder easily. He overpaid Kosuke Fukudome, a corner outfielder with a lack of power. He signed Carlos Zambrano to a big extension. He signed Milton Bradley at all.

Yet, I’d argue that Jim Hendry’s worst actual decision was signing Carlos Marmol to his current extension, which bought out a year of Marmol’s free agency at $9.8 million. Let’s look at the competition.

Sure Soriano was overpaid, but it was similar to the idea behind the Angels signing Albert Pujols. You know the contract will be bad at the back end, but hope to get an elite talent at the front end. And Soriano was elite in the first two years of that contract, contributing more than 10 fWAR in valueas the Cubs made the playoffs both years. On top of that, Soriano was signed specifically under orders from management to increase payroll to raise the value of the franchise.

Carlos Zambrano quickly declined following signing his extension, but from 2003 to 2006 was one of the most consistent pitchers in baseball. Kosuke Fukudome was still in that ordered adding payroll phase, and had dominated Japanese baseball sufficiently to be arguably worth the risk.

OK,Milton Bradley was a disaster. Not only was Bradley a well known malcontent, but to expect Bradley to be able to play regularly in Wrigley’s right field at that point of his career was optimistic at best, if not down right foolhardy. But I understood the move. The Cubs were trying to take that last step to getting to the Series before the sale from the Tribune. It was a disaster, and was clearly one very quickly.

Yet I still don’t find it as bad as signing Marmol to that extension. Here is my problem with the extension: it was rewarding Marmol for past success, not paying him for expected performance. Any baseball personnel man worth his salt should have realized Marmol, a high strikeout, high walk, high stress pitching motion reliever who relied on an ability to locate an inconsistent but devastating slider was someone who was unlikely to have a long peak. Any baseball personnel man should also have realized that even a great reliever doesn’t turn a bad team into a good one. You ride the Carlos Marmols of the baseball world through arbitration and let them go, or trade if you’re out of it. Yet the Cubs were stuck with Marmol an additional season in a year that Hendry should have known he had a high likelihood of ineffective. As a result, the Cubs were both unable to trade Marmol a year earlier, and now will be paying him nearly $5 million to play for someone else.

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Noah Eisner is a Chicago attorney living in the western suburbs with his wife and son (and impending daughter). When he isn’t practicing law or entertaining a toddler, Noah follows Cubs baseball with a focus on the farm system and sabermetric analysis. His Cubs-related ramblings can be followed on Twitter @Noah_Eisner.