Jim Hendry, Kenny Williams

The best and worst from Cubs GM Jim Hendry


A look at the highlights and lowlights from Jim Hendry’s nine-year tenure as Cubs GM, which ended with his dismissal on Friday.

Best moves

July 23, 2003: Acquired 3B Aramis Ramirez and OF Kenny Lofton from Pirates for 2B Bobby Hill, INF Jose Hernandez and RHP Matt Burback

I called it “highway robbery” on Rotoworld at the time, and it proved to be that and so much more.   The Pirates gave away Ramirez even though he had just turned 25 and he was hitting a solid .280/.330/.448 for the season.  He’s hit 236 homers for the Cubs since.

Nov. 25, 2003: Acquired 1B Derrek Lee from Marlins for 1B Hee-Seop Choi and RHP Mike Nannini

On the other hand, I slammed this one, believing Choi was just about as good as Lee already.  Lee went on to make two All-Star Games and hit 179 homers in seven seasons with the Cubs.

Jan. 21, 2004: Signed RHP Ryan Dempster to one-year, $500,000 contract with a $2 million option for 2005

The Cubs took a chance on Dempster as he was rehabbing following Tommy John surgery.  He rewarded them with a fine season as a closer in 2005, and while he wasn’t such a good reliever the two years after that, he’s won 53 games as a starter the last four seasons.

Nov. 14, 2006: Signed infielder Mark DeRosa to a three-year, $13 million contract

This is another move I was none too impressed with at the time.  However, DeRosa had two fine seasons as a Cub, hitting .289/.373/.451 with 31 homers, and the team was then able to trade him to Cleveland for three prospects, one of whom, Chris Archer, proved to be the key component in last winter’s deal to land Matt Garza.

Worst moves

I’m listing the moves that were pretty obviously poor at the time, in my opinion.  I didn’t mind the Carlos Zambrano extension, and I’m not going to get on Hendry’s case for the prearranged trade in the Rule 5 draft that had Josh Hamilton passing through Chicago on his way from Tampa Bay to Cincinnati.

Dec. 7, 2005: Acquired OF Juan Pierre from Marlins for RHP Ricky Nolasco, RHP Sergio Mitre and LHP Renyel Pinto

The Cubs made three significant trades with the Marlins in the first half of the decade.  The Lee deal worked out great, but the Pierre trade was a bust and sending Dontrelle Willis to Florida for Matt Clement and Antonio Alfonseca could have turned out even worse if Willis didn’t fall apart.  The ugly thing about the Pierre deal is that he was just one year away from free agency, yet the Cubs gave up three live arms for him anyway.  He had a typical Pierre season and then signed with the Dodgers.

Nov. 20, 2006: Signed outfielder Alfonso Soriano to an eight-year, $136 million contract

It was the second biggest deal ever given to an outfielder, behind Manny Ramirez’s contract with Boston, and even five years later, it stands at No. 3 on the list.  Soriano started the eight-year pact out with two fine seasons, but he’s been at best an average regular since and there’s still three more years to go.

Dec. 31, 2008: Signed infielder Aaron Miles to a two-year, $4.9 million contract

I picked this one over the Neifi Perez infatuation.  Miles ended up playing in 74 games for the Cubs and hitting .185/.224/.242 with a remarkable five RBI.

Jan. 9, 2009: Signed outfielder Milton Bradley to a three-year, $30 million contract

Bradley was coming off an exceptional season with the Rangers, but it was one in which he had his usual problems staying healthy even while serving primarily as a DH.  Bradley turned out to be a disaster with the Cubs, hitting .257 and driving in 40 runs in his one year with the team before being dealt for an even worse contract (Seattle’s Carlos Silva).


In my opinion, it was long past time for Hendry to go.  He had some good instincts when it came to players to pursue on the cheap, but when he was given money to spend, he typically did so unwisely and his drafts were often disappointing.  In fact, not one of his first- or supplemental first-round picks has turned into an asset yet, and for a GM on the job for nine years, that’s pretty damning.

I think Hendry might have been better off as the GM of a small-market team (preferably with better scouting directors).  There would have been no Soriano, Bradley or Kosuke Fukudome.  Forced to limit his expendatures, Hendry might have come up with more Dempsters, DeRosas and Marlon Byrds.  It’s not that his tenure was a total disaster, but the Cubs job probably wasn’t ever the right one for him.

Kyle Schwarber is on a private plane en route to Cleveland

PHOENIX, AZ - APRIL 07:  Kyle Schwarber #12 of the Chicago Cubs bats against the Arizona Diamondbacks during the MLB game at Chase Field on April 7, 2016 in Phoenix, Arizona.  (Photo by Christian Petersen/Getty Images)
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This is happening, people.

Earlier we heard Joe Maddon being non-committal about Kyle Schwarber joining the Cubs for the World Series. Now it seems pretty clear that the Cubs are committal indeed: Jon Morosi reports that Schwarber is en route to Cleveland from Arizona on a private jet and that he’s expected to DH in Game 1 tomorrow night.

Schwarber hasn’t played in a game that counted since April 7. His potent bat is could be a windfall for a Cubs team that didn’t have a game-changing option at DH in the American League park.

Schwarber lost the whole season due to a knee injury, but he hit .246/.355/.487 with 16 homers and 43 RBI in 69 games as a rookie in 2015. His big coming out party was in the playoffs, however, when he hit three homers in five postseason games while going 7-for-13 with two walks in five games.

Carlos Santana in left field? Sure, OK.

CLEVELAND, OH - OCTOBER 15:  Carlos Santana #41 of the Cleveland Indians celebrates after hitting a home run in the second inning against J.A. Happ #33 of the Toronto Blue Jays during game two of the American League Championship Series at Progressive Field on October 15, 2016 in Cleveland, Ohio.  (Photo by Maddie Meyer/Getty Images)
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Paul Hoynes of the Cleveland Plain Dealer reports that Indians First Baseman/DH Carlos Santana shagged some flyballs in left field during the Indians’ workout today.

Sure, why not? Santana has played one game in the outfield in his major league career and that was over four years ago, but the Indians will have to play in Chicago without the DH, meaning either losing Santana’s bat or that of Mike Napoli.

It would be up to Terry Francona to decide if that happens, but ultimately I don’t think he’ll make it real and, rather, will just forget about it, because Santana’s defense out there would in no way be smooth.

I’m sorry. I’m sick today and I’m on a lot of cold medicine.