Cubs Q&A with Ted Lilly: Winning it all, next steps, Kyle Hendricks

Cubs Q&A with Ted Lilly: Winning it all, next steps, Kyle Hendricks

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."

The Craig Kimbrel Conundrum: Closer a major question mark for 2020 Cubs


The Craig Kimbrel Conundrum: Closer a major question mark for 2020 Cubs

The last time Cubs fans saw Craig Kimbrel on the mound, he was staring bewildered at the left-field bleachers after serving up homers to the Cardinals on back-to-back pitches. It was a moment that became the dagger for the 2019 Cubs, even if it didn't officially eliminate them from postseason contention.

That Sept. 21 outing marked Kimbrel's third blown save and fourth loss of the season and the Yadier Molina and Paul DeJong homers were the eighth and ninth longballs the Cubs closer gave up in just 23 outings and 20.2 innings.

Nobody associated with the Cubs saw things playing out quite like this when they signed him in early June. Even Kimbrel's doubters who believed his struggles at the end of his Red Sox tenure were a harbinger of things to come couldn't have anticipated a 6.53 ERA and 1.60 WHIP from a guy who had a career line of a 1.91 ERA and 0.92 WHIP coming into 2019.

So where do the Cubs go from here?

Kimbrel is still owed $16 million for 2020 and 2021 and is the only truly established pitcher the Cubs currently have in their bullpen for next season with Steve Cishek, Brandon Kintzler, Pedro Strop and others ticketed for free agency.

The Cubs opted to shut down Kimbrel for the final week of 2019 to get healthy after dealing with knee and elbow issues but neither injury will require surgery this winter, Theo Epstein said.

"He's really determined to have a great offseason and looking forward to a full and legitimate spring training," Epstein said. "He feels awful about the way this year went, recognized that he was in an unusual position, but I think you'll see a really determined individual who will benefit from the full spring training."

The Cubs better hope so.

For a franchise that is going to again have to take their budget into account when building the 2020 roster, that $16 million price tag is an awful lot if Kimbrel cannot return to the elite closer he was before coming to Chicago.

But even beyond that, the Cubs absolutely need him to lock down the ninth inning. Rowan Wick impressed in 2019 and emerged as maybe the team's best reliever down the stretch, but he doesn't have much of a track record. The same goes for lefties Kyle Ryan and Brad Wieck. The Cubs have reason to feel optimistic about all three pitchers as up-and-coming relievers, but putting too much stock into a trio of guys without much experience is an easy way to run into major bullpen problems. 

Right now, those are the only four names you can confidently pencil into the 2020 bullpen, though other in-house options loom (Tyler Chatwood, Alec Mills, Danny Hultzen, Duane Underwood Jr., etc.) depending on how the Cubs configure their rotation and the rest of the roster.

There's obvious concern surrounding Kimbrel, but there's also a reasonable case to be confident 2020 will be a different story. In his entire career, he has served up homers at a rate of just 0.72 per 9 innings, so his 3.92 HR/9 this season is a clear aberration that not even the juiced ball can full explain away. 

The velocity dip (down nearly 1 mph from 2018 and 2 mph from 2017) is scary, but may also be related to the odd year Kimbrel had. 

Baseball players — and closers, in particular — are very routine-oriented and no plan can make up for a situation that saw Kimbrel facing live hitters nearly four months later than usual. He's used to throwing off a mound and ramping up in spring training in mid-February and was instead still in a free agency stalemate until early June.

When he was signed, it was viewed as a clear upgrade for the Cubs, who were plagued by early-season bullpen issues. They were only able to afford Kimbrel because Ben Zobrist took a leave of absence and left several million dollars on the table for Epstein to put towards addressing an obvious weakness on the roster.

At the time, signing a World Champion closer on a Hall of Fame trajectory was the best possible way Epstein could shore up the bullpen.

"There was some element of risk, because of the unknown of an elite closer coming in mid-season," Epstein said on the team's final road trip. "That's a risk we were prepared to take because of the opportunity that presented itself. The resources got opened up with Zo's absence and the opportunity of an elite closer sitting there for a contract that was certainly reasonable compared to what most guys of his ilk were getting over the long-term. 

"So, we were prepared to take that. We thought it was a really good fit and we were prepared to take that risk. It hasn't turned out as we had hoped. It obviously [killed] Craig that he wasn't able to help down the stretch here. The two trips to the DL and not being able to reach his accustomed level on a consistent basis, you have to think it's related to not having his normal foundation underneath him. It's something we'll certainly talk to him about and how to have a really effective offseason and get back to his normal Spring Training, so he can get back to being himself consistently."

Cubs add two more managerial interviews this week

Cubs add two more managerial interviews this week

Though not every managerial candidate wants the Cubs job, Theo Epstein's front office will add two more interviews to their docket this week.

Carlos Beltran reportedly does not want to take the Cubs gig and is holding out only for the Mets opening. However, the Cubs are moving on and will interview Astros bench coach Joe Espada and former Phillies manager Gabe Kapler this week. 

Espada has been a rumored target of the Cubs, but he has been understandably tied up with Houston's playoff run. The Astros have a day off Monday before continuing their ALCS battle with the Yankees, and Espada is reportedly at Wrigley to meet with Epstein and Jed Hoyer:

Espada, 44, is one of the hottest names on the managerial market this fall and has served as A.J. Hinch's bench coach in Houston for the last two seasons. He has also worked as a minor-league coach and third-base coach for the Marlins, spent a year as a special assistant to Yankees GM Brian Cashman and another three seasons as the Yankees infield/third-base coach.

Kapler, 44, was just fired from his post as Phillies manager last week after two disappointing seasons in Philadelphia. In his first gig as manager, the former MLB player went 161-163, including just 81-81 this season with a roster that added Bryce Harper, J.T. Realmuto and Jean Segura before the year. 

The Cubs have already interviewed four candidates, with current bench coach Mark Loretta going first in early October. Last week, David Ross, Joe Girardi and Will Venable also met with Epstein and Hoyer. 

In his end-of-season presser, Epstein said the Cubs are "full speed ahead" with their search for a new field general. Among other qualities, the Cubs front office is looking for a manager who can cultivate a winning culture and find a way to ensure the whole is greater than the sum of the parts — an issue that plagued the team the last couple seasons (though that's not necessarily Joe Maddon's fault).

"The next manager will be a success if he can find a way to get the most out of each player," Epstein said. "That’s an obvious goal, but we want to make sure that the players we have, we’re reaching them, we’re developing them, we’re providing an environment where they can continue to grow and thrive. If we have players that are gonna be successful major-league players, we have to find a way to make it here. 

"I think that’s really important. That’s an organization-wide challenge, not just on the manager. The next manager, that’s going to be an important part of his responsibility."