Hendry's Greatest Misses, 2008-2009 Edition

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Hendry's Greatest Misses, 2008-2009 Edition

The reaction of some Cubs fans to this past offseason has been focused on a single trade: Mark DeRosa for three minor leaguers. According to many, Brock-for-Broglio is now #2 in “Worst Trades in Cub History.” The Cubs gave away the greatest player in Cubs history (next to Mark Grace, of course). In fact…

Mark DeRosa doesn’t read books. He just stares them down until he gets the information he wants.
Mark DeRosa’s hand is the only one that beats a Royal Flush.
Mark DeRosa can kill two stones with one bird.

While Mark DeRosa has been retroactively turned into Cubs’ fans version of Chuck Norris, it’s important to realize that there’s been a series of bad decisions, bad luck, and general crappiness that has lead to the blech that currently surrounds this Cubs team. Starting in July 2008, from top to bottom , this organization has made significant mistakes that, while they can certainly be overcome, have nonetheless put this team into a much bigger hole than most of us had anticipated for the 2009 season. While there are plenty more mistakes strewn about the organizational moves that have occurred over the last 3-4 years, but here are some of some of the most significant contributors to the Cubs’ current problems over the last year NOT including the Mark DeRosa trade:

#1: July 31, 2008-The LA Dodgers trade for Manny Ramirez

Without Manny Ramirez, the Dodgers would ne-eh-eh-eh-eh-eh-ever have won the West last year. Although I didn’t realize it at the time, the Dodgers were the single worst matchup the Cubs could have had in the playoffs last year. No team in the playoffs had a series of excellent control/sinkerballing right handed pitching that would highlight the Cubs’ general right-handedness. Of course, losses in these three games would mean more than the wins in 97 other games, because...

#2: October 2008-Jim Hendry Watches Playoffs

Could someone have simply lured Jim Hendry to some tv-less island in the Pacific with the promise of honey glazed delicacies during the 2008 playoffs? Yes-the Cubs had a lot of right handed hitters. In 99.9% of the situations, it wouldn’t have made a huge difference. In fact, it didn’t make that much of a difference in the 2008 playoffs (Ryan Dempster’s inability to throw strikes, along with about 1,000 other things, should be listed before “too right handed” comes in). Unfortunately, in true Jim Hendry fashion, he saw a single (minor) problem, decided to fixate on that problem, and built an entire offseason on a philosophy that really wasn’t going to make this team better. Speaking of philosophies that won't make the team better…

#3: November 14, 2008: Cubs trade Jose Ceda for Kevin Gregg

Why is it when Jim Hendry openly declares that he wants to address a certain position in the offseason (in this case, the bullpen), he rarely succeeds in making the position better, but most certainly makes the position more expensive?

Year to year, the least predictable position on every single team is the bullpen. All bullpen pitchers are inherently limited. If they were truly solid, consistent pitchers, they’d be starters. The only thing that is guaranteed by signing middle relievers to contracts over $1 million per year is that you’re going to waste money. Yet Jim Hendry does it year after year. After year. After year.

Kevin Gregg is a mediocre middle reliever. So, really, is Aaron Heilman. There is almost no difference between Angel Guzman and Aaron Heilman, except maybe $1.5 million.

The Cubs will pay $9.5 million to relievers not named Carlos Marmol this year. Think about that a little bit, then try and not swallow a bottle of aspirin.

#4: November 18, 2008: Cubs re-sign Ryan Dempster

Ryan Dempster had a career year last year and a significant amount of it was due, unfortunately, to luck. Virtually all of his peripheral stats indicated that his shortcomings didn’t quite impact his overall numbers in the way they should have.

While Dempster is a decent starter, Hendry yet again jumped the gun and overpaid without letting the market dictate the best course of action. At the news conference announcing the signing, Hendry said, “"It was imperative that we kept him in-house. No doubt in our minds that Ryan would have exceeded this deal on the streets in three or four weeks from now, the way the market is for starting pitching.”

Unfortunately, the market didn’t quite respond the way he thought it would. Aside from the Sabathia and Burnett signings, very few of the Free Agent pitchers did better than Dempster, who unfortunately may be what he’s been for the majority of his career (i.e. a 4th starter) over the next four years.

#5: December 31, 2008: Cubs sign Aaron Miles

I played in a Six-Foot and under intramural basketball league in college. It was nice-all of us short, sad players were put on the same level and didn’t have to deal with 6’5” trees making us feel bad with all their “talent.” Apparently, Jim Hendry needed extra players for the MLB version of the Six Foot and Under league.

It wasn’t just that Aaron Miles sucks. Or that he sucks. Or that he sucks. It’s that, once again, Hendry completely misjudged the market, bid against himself (AGAIN), and paid 2.5 mil per year for a guy he could have gotten for $500,000 a month and a half later. Take a look at the infielders who signed this offseason:

Orlando Hudson: 1 year, $3.4 million ($4.6 in potential bonuses)
Ray Durham: Unsigned
Mark Grudzielanek: Unsigned
David Eckstein: 1 year, $850,000
Adam Everett: 1 year, $1 million
Alex Cora: 1 year, $2 million
Felipe Lopez: 1 year, $3.5 million
Joe Crede: 1 year, $2.5 million
Aaron Miles: 2 years, $4.9 million

This is a list of players who aren’t very good. Still, I’d take every single one of them over Aaron Miles-and Aaron Miles, considering both cost and length of contract is the MOST EXPENSIVE PLAYER ON THIS LIST.

While overreacting to 21 games is a little ridiculous, I don’t think it’s too early to begin to critique some of the moves Jim Hendry made this offseason. This GM has consistently been able to gloss over his mistakes by throwing unprecedented amounts of money at the Cubs’ shortcomings. Realistically, there is virtually no way to spend $134 million on a team (in a division in which no team spends near that much) and not be the best team. But, unlike GMs like Theo Epstein who spend a lot of money but also develop from within, Hendry has been unable to develop a minor league system that can fill gaps on the major league team-hence the need to consistently overpay for mediocrity.

Given the current financial situation of the Cubs, Hendry will have to actually be a real GM for the next year or so. So far, the returns aren’t good. The core of this team is aging quickly (some much more quickly than others, right Derrek?). If Hendry continues to show an inability to do what needs to be done within a budget, the next few years could be ugly.

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