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How The Cubs Got Ted Lilly

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Former Cubs front office member Chuck Wasserstrom gives the inside story of one of the most famous incidents in recent Cubs history.

Photo by Jonathan Daniel/Getty Images

This story was in Cub Tracks yesterday, but it deserves its own story. Chuck Wasserstrom, who was a member of the Cubs baseball operations staff in 2006 under then-general manager Jim Hendry, wrote the history of the Cubs at the Winter Meetings that year and how the Cubs signed Ted Lilly for MLB Trade Rumors.

Go read the story. It is totally worth your time.

You probably remember the outline of that story: Hendry was in the hospital suffering from heart problems as he landed free agent left-hander pitcher Ted Lilly for four years and $40 million. But what Wasserstrom reveals through both his own memories and from talking to other people who were there, including Hendry, Lou Piniella, Lilly, Lilly’s agent Larry O’Brien, Yankees GM Brian Cashman and others, is that Hendry was so focused on making Ted Lilly a Cub that he could have died making the effort. In the end, O’Brien famously called Hendry to say they had a deal as Hendry was stretched out on a gurney with an EKG machine hooked up to him. Right after that, they put Hendry in an ambulance and rushed him to a different hospital where he had a procedure done that most probably saved his life.

I know that Hendry is a controversial figure around here, but I hope that no one can deny after reading this article that Hendry was a tireless worker who would do anything to make the Cubs a better team, including dying. OK, he wasn’t really willing to die for the Cubs — he was living in denial that putting off going to a doctor until after he signed Ted Lilly was putting his life in danger. But that’s pretty close to “willing to die for the Cubs.”

I’m quite familiar with Hendry’s failings as a GM. The club was slow to adopt analytics. The farm system wasn’t as productive as it should have been and he gave out too many big contracts to veterans who were in decline. He was always robbing tomorrow to pay for today.

But under orders from the Tribune to do what it takes to turn the Cubs into a winner, Hendry took a team that had lost 96 games in 2006 and won back-to-back NL Central championships in the next two seasons. Three members of the Cubs World Series Championship team — Javier Baez, Willson Contreras and Matt Szczur — were all signed by Hendry. In addition, Theo Epstein was able to take some of those veteran players and spin them off for many other key members of the current Cubs. Hendry hatched a plan to draft Jeff Samardzija in the fifth round and convince him to give up football. Because of that, Theo Epstein was able to turn Samardzija into Addison Russell.

Oh, and Jim Hendry signed Ted Freakin’ Lilly. We should at least thank him for that.