Presented By Mooney

MESA, Ariz. – Nothing summed up the win-one-for-the-Tribune Tower frenzy – and the passion felt by generations of Cubs fans – quite like this story: Former general manager Jim Hendry finalizing Ted Lilly's four-year, $40 million deal while hooked up to an EKG machine in a Florida hospital room during the winter meetings.  

That spending spree coming off a last-place finish in 2006 would lead to back-to-back division titles in 2007 and 2008, so much entertainment with larger-than-life personalities like Lou Piniella and Alfonso Soriano, two crushing playoff sweeps, years of ownership instability and ultimately a reckoning that would reshape the entire franchise. 

Theodore Roosevelt Lilly III rejoined the Cubs as a special assistant to the president and general manager three years ago during spring training, reporting to Arizona to offer his insight as someone who experienced Chicago's sky-high expectations and bitter disappointments.   

Q: Looking back on 2016, what separated that group from the other 100-something teams that came before?    

A: "This thing has been growing here for the last few years, this new culture of winning. The team that did this is special – talented, young, a lot of maturity for a young team, just impressive all the way around. There's some talent, but there's also some really good baseball players. Watching these games, these guys do a number of things that don't show up necessarily on individual statistics that help the team win games. 

"These guys have also (been) put into a really good environment to succeed. I think our player development did a good job. And at the big-league level as well, you've seen them get better."


Q: What did it mean for you to be part of the organization when the Cubs finally won it all?

A: "I understood the feeling of how special accomplishing that dream was. When I was here as a player, it was something that we talked about quite often, trying to make that a reality and all the different ways to try and get that done. 

"Having the opportunity to come over here and be a part of this, obviously I feel extremely fortunate to be involved in the organization in any capacity. I wasn't able to get a ring as a player and wanted to be connected with this organization. Early on, there were a lot of things going on here where you could envision this potential, this possibility of the Cubs finally getting it done."

Q: How would you describe Theo Epstein's management style?

A: "No stone left unturned. (Not that I'm around much, but) I've also witnessed a lot of trust that he has in the team (and everyone who's) involved in it. That was something that I just wasn't aware of – that it's on a level like that where there are these open arguments of opinions. Even if they're adamant, there's still this open-minded respect for the other guy's opinion (during these) high-level evaluations. (The draft room) is a great example."

Lilly has three young children and earned roughly $80 million during his playing career, according to the salary database at, absolutely maximizing his talent as a 23rd-round pick who earned two All-Star selections and lasted 15 years in the big leagues. Those would appear to be the opposing forces – comfortable stay-at-home dad vs. potential pitching specialist – in his second baseball act.  

Q: Do you have a sense of what you'd like to do next after getting your feet wet in the front office – something more or something different?

A: "It's hard for me to pin it down exactly as we sit here right now. I really like what I'm doing, just getting the opportunity to be around and learn from many different people, keeping my ears open and paying attention. 

"Whether it would continue to be here, which would be ideal, or go somewhere else, (I don't know). But from the people I'm around, there's just a lot to learn, like Joe (Maddon) and his ability to communicate."

There's obviously a left-handed/right-handed difference, but in the same way that Lilly used his smarts, guts and competitive nature, Kyle Hendricks showed that a frontline starter doesn't necessarily need to have a 6-foot-5-inch frame and 100-mph heat.

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Q: Could you explain what Hendricks did last year in going from a pretty good fifth starter to an ERA leader?


A: "If someone asked me: ‘Do you think Kyle Hendricks' stuff is pretty good?' I do. That term gets thrown out often. I also think of movement as stuff. That's a part of stuff. On both his sinker and his changeup, there's quite a bit of movement – and it's late and it's in the right direction. 

"So it may not have the numbers on the radar gun that we typically equate to stuff. But as far as depth in the zone – you watch how he can throw a breaking ball at whatever the velocity is – there's still some bite to it, which I consider to be pretty good stuff. If you can get a ball to move late, it's hard to hit. 

"Kyle and I are different styles, not so much the left- and right-handed thing, but also the movement. I didn't have the ability to make a pitch sink the way that he does. It's pretty special. And an X-factor that is a separator for him, without question, is the command."

The Cubs never would have added Hendricks to their minor-league inventory in the summer of 2012 if the Randall Delgado trade with the Atlanta Braves hadn't collapsed, and Ryan Dempster hadn't backed off his strong preference to go to the Los Angeles Dodgers and play with Lilly again.    

In a buzzer-beater before the July 31 deadline – on a day where Dempster played Golden Tee in the employee lounge, kicked up his feet up on a staffer's desk and watched the MLB Network coverage inside the team's Clark Street headquarters – the Cubs finally reached an agreement to waive his no-trade rights and acquire two Class-A prospects from the Texas Rangers.   

Q: Were you in the loop on that Dempster deal?

A: "Just a little bit, because there were some questions that were asked from our front office at the time about acquiring him. But I was a player, not front-office personnel. My involvement was very minimal. Ned (Colletti) had asked me questions about what we were getting, and I certainly made it clear that I believed he would help us.

"We're all glad that he went to Texas."