Chairman on Cubs season: 'With all the disappointment we have, there's a lot of optimism as well'

MILWAUKEE - Just like millions of fans, Tom Ricketts is hurting.

A few weeks ago, the Cubs' chairman thought for sure his team would be playing postseason baseball, but a September collapse kept that from happening.

"We set out a goal to make the playoffs and we didn't get there," Ricketts said during the Cubs' season finale at America Family Field on Sunday.

Ricketts spoke for almost 15 minutes, addressing Cody Bellinger's impending free-agent status, David Ross' work in the dugout and more.

Q: How did the season feel to you?

A: "It kind of felt like it was four different seasons. We got off to an OK start, then we slumped, then we rallied back, and of course September's been so rough.

"It's tough to not achieve your goal and it's tough when you're just a couple games away from making the playoffs. And it's extra tough that for a while there it looked pretty likely.

"So it feels like something got taken away.

Q: Can this be considered a good season if you don't make it to the playoffs?

A: I don't think that we want to start calling seasons we don't make playoffs good seasons. That's a consolation prize and we don't play for consolation prizes. With that said, there were some great moments and great performances. There was a lot of excitement and the organizational health is as strong as its been in a long, long time. So with all the disappointment we have, there's a lot of optimism as well.

Q: Do you believe you can be aggressive in the free-agent market this winter?

A: Well, I mean we were aggressive this year and I think we'll stay in those levels. I'll let Jed (Hoyer) decide where the dollars go. But the nice part is we do have a fair number of (players) coming through the system that could be real producers the next few years.

"And on top of that, we have a core. (That's) something we couldn't say two years ago. We have a handful of guys who are going to be here for the next few years and we've got five or six positions locked down for next year with guys who are well above major league average players.

"That's a great start. So it'll be up to Jed to figure out (how) to supplement those guys to put a winning team on the field."

Q: Fans would say, "Just re-sign Cody Bellinger." Can you take that distant view as a fan when thinking of doing that?

A: "I don't have to (take) a distant view of a fan. I mean, I am one and I've talked to thousands of them. Yeah, I get it. We'd love to have him back, but that's something that'll be up to the baseball guys.

Q: As a matter of philosophy should the Cubs be a team that keeps their best players even if it means paying for them, especially someone who is at an MVP level?

A: "Yeah, I mean in general. There's something to keeping your best players. Obviously we extended Ian (Happ) and Nico (Hoerner) this year. We've got six more years of Dansby (Swanson). So we've got a good core that we're definitely holding onto.

"It'd be nice. It'll be up to Jed, Cody and the free-agent market."

Q: One of the things you are wary of is handing out contract that are too long, though, right?

A: "The dollars you spend per year is one thing, but you've seen contracts go nine, 10, 11 years. We just have to be very careful when that's the market standard because obviously players typically decline over those years pretty substantially. Other teams are paying the price for some of those contracts.

"Jed's done a very good job of making sure our contracts are rational, and I'm sure he'll do the same thing this off-season.

Q: Will the Cubs compete for a World Series in 2024?

A: "The way we look at it is we want to have a team that can make the playoffs every year. There's a lot more upsets and surprises in baseball playoffs and the key to consistency is to not build a one-year superteam but to get to the playoffs as often as possible.

"And you do that by finding guys you like, giving them extensions, solidifying your core and then trying to supplement them with guys through your system and the occasional free agent.

"That's gonna be our strategy going forward."

Q: What are you most proud of about this season?

A: "The way the players responded to the adversity they faced in June when we had a bad West Coast road trip. And I think a lot of players and a lot of teams - being 10, 12 games under (.500) - would decide the season was over and just mail it in.

"Instead, the guys came back and pushed really hard ... and made their case to add as opposed to subtract (at the trade deadline)."

Q: Is David Ross the right manager to lead a team to the World Series?

A: "I think Rossy had a great season and the players play hard for him. He's our guy. I like him a lot. ... Once again - going back to what (I'm) proud of - when the team got down way below .500 and it looked like the season was over, he didn't let it go.

"He got the guys back and playing hard, and we got to here. He was a big part of that. He's a great manager."