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Must Read of the Day: The Story Behind the Story of the Famous From-the-Hospital Ted Lilly Signing

Chicago Cubs News

“No general manager is going to say, ‘Oh gee, I don’t want to do that. I don’t want to spend the money.'”

Jim Hendry, the former General Manager of the Chicago Cubs, was an important, transformative leader in Cubs history.

He may not have been the guy to bring the Cubs all the way, but he did steer the Cubs to three postseason runs in six years and was, perhaps infamously, just five outs away from delivering the first World Series to the North Side in nearly 60 years.


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He also played a non-zero role in the Cubs’ recent World Series win, by bringing in Willson Contreras, Javy Baez, and many others (including by way of trades that happened after he left). Needless to say, he’s one of the most important figures in recent Cubs history.

Near the end of his tenure with the organization, he was tasked with spending whatever he could to drive up the value of the team in 2007, as the Tribune Company secretly planned to sell the Cubs. On those orders, Hendry brought in guys like Mark DeRosa, Alfonso Soriano, and even Lou Piniella, while extending Aramis Ramirez, Kerry Wood, and Henry Blanco. Going worst to first was the plan, and Hendry had a blank check.

Despite all of the additions on the positional side, however, Hendry knew that the team still needed pitching. And it was the story behind his hospital bed signing of Ted Lilly that sparked your must-read of the day.

At MLB Trade Rumors, Chuck Wasserstrom has a long, but worthy read about Jim Hendry during his time with the Cubs entitled: “Straight From the Heart: The Signing of Ted Lilly, and I’m giving it my stamp of “you-must-read-it-today.”


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At its highest level, this is a great peek behind the curtain of a GM heading into the Winter Meetings with a checkbook and a directive to win – which, yeah, that’s awesome. This amount of intimate, organizational details regarding free agency is rarely shared willingly.

But beyond that there’s a really great story to be read.

When the Winter Meetings kicked off, Lilly was looking around the league for a contender – somewhere he could spend the next 4-5 years winning. The Cubs weren’t exactly that team, but the signing of Soriano got his attention.

Meanwhile, Jim Hendry was rolling around in his bed, fighting chest pains that would last two to three minutes at a time. “I barely slept last night. I was afraid that if I closed my eyes, I wouldn’t wake up,” he said. He knew something was wrong, but knew he had a job to do, as well. His coworkers – including Lou Piniella – however, were more determined to get him to the hospital. And that’s exactly what they did … just after he shoved a 4 year/$40 million deal across the table to Ted Lilly.

The crazy part, if you can believe it, is what happens next.


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That’s where Jim Hendry describes taking a call from Lilly’s agent … while Hendry was on a gurney … hooked up to an EKG machine. And it didn’t end there, he continued being the GM as the doctors and medical staff were prepping him for a procedure – and not one that was run-of-the-mill. You may know the story in general, but you’re definitely going to want to read the details (that wasn’t the last deal he consummated from the hospital, for example).


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Lilly gave the Cubs his best season in 2007 (3.8 fWAR over 207.o IP), and the spending spree helped push the Cubs into the playoffs. Even though it didn’t work out for the Cubs that year, I don’t think anyone regrets a thing at this point. Jim Hendry is a heck of a man, and clearly gave his all to the Chicago Cubs.

Do yourself a favor and read all about it.


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Michael Cerami

Michael Cerami is a Writer at Bleacher Nation, and you can find him on Twitter at @Michael_Cerami.