Cubs Insider Q&A With ESPN Chicago’s Jon Greenberg: Next Phase, Maddon, TV Deal

I recently got the chance to visit with ESPN Chicago columnist Jon Greenberg in order to discuss the current state of the Chicago Cubs.

Greenberg, in my opinion, does some of the finest work in town. Ok, I may be biased because I consider him a friend. Even so, his takes on the Cubs have been fair and he’s able to find the lighter side of the ugliness that has come with the past three years of tanked seasons.

Today we discuss the front office entering the next phase for the organization, Joe Maddon and his future with the Chicago media, and the next important domino to fall for the business side.

TL: Does Theo Epstein appear to be a different guy? One that now is clearly relieved that the three seasons of tanking are behind the orginization? Are we about to see this front office’s competitive nature kick into full gear here?

JG: He (Epstein) seemed very happy at the press conference, cracking jokes and whatever. Why wouldn’t he be? He landed one of the top five managers in baseball.

No one’s crying for these guys, but rest assured they weren’t thrilled to come to the park to watch games during some of these lean times. So yeah, with Maddon in tow, additions will be more suited to building a winning team, not taking flyers on guys at low, low prices. But it’s not an all-or-nothing offseason. I’d be shocked if they trade any real prospect without getting a young star in return in the next year.

TL: How telling was it in regards to Dale Sveum and Rick Renteria that Epstein remarked that Joe Maddon would always be one of those guys they could see as long-term answer at manager?

JG: Pretty telling. He added a caveat of “if it didn’t work out” in regard to Sveum and Renteria, but the point was clear. Obviously we all thought those guys weren’t keepers in the long term, particularly Ricky. So hey, we’re not always wrong!

TL: Are the Cubs indeed setting themselves up for some public blowback if they don’t sign one of the top FA’s this offseason?

JG: Yeah, I think so. Theo did one of his “We welcome your wrong criticism!” things after the season ticket event, noting my criticism would at least be funny. It’s only natural for fans, and reporters, to expect some action this offseason. Theo’s talking playoffs and that carries some weight and responsibility. And we’re a big-name society, even if salary isn’t always predictive of performance. Basically everyone wants Tom Ricketts to put some money into the lineup. That’s not wrong, but I wouldn’t deem this offseason a failure if they don’t get Jon Lester.

TL: How happy is the business side that they can finally start promoting the kids/winning and bringing a mega personality like Maddon into the fray?

JG: As one business side guy said to me during the Maddon courtship, “Winning is good for everyone.” Remember those people are judged on what they do today, not on the promise of tomorrow.

TL: Some local media almost seem to wear the beating down of past managers like a badge of honor. How quickly will they test Maddon and how do you think he will respond over the course of the season?

JG: Well, I think it’s more gallows humor than anything. We’ve seen a murdered row of managers come in rosy-cheeked and leave red-assed. Look at Dusty. He came in off a World Series appearance and by 2006, he was ready to go. I don’t think the media here is particularly tough, or unfair, but we are there every day with questions. Every day. And yes, the losing stink of this franchise, both historically and now in the Ricketts era, permeates our questions and coverage. How could it not?

But I think Maddon will be fine. Tampa Bay has a bigger media contingent than you’d think, but I’m guessing he’ll be a little surprised at the volume of Cubs coverage from writers and radio folks. But he’s pretty savvy and very easygoing. I think there will be a better rapport with reporters.

Dale was great to us, honest to a fault. Ricky, from what I heard, was nice but not very helpful. (Here’s where the peanut gallery says “So what?” We’re not out there asking questions for own benefit or trying to win a Pulitzer. We ask questions to get fans answers.)

Maddon’s going to get more coverage as the team gets more attention. I, for one, haven’t been to too many postgame press conferences since Sweet Lou left.

TL: What will it take for 2015 to be viewed as a success?

JG: They have to be relevant in August, though first they have to relevant in April, May, etc. I’d say .500 ball is a nice easy number to shoot for. I’d like to see a wild card run. The fans sure deserve it.

TL: Are Cubs in position to close a TV deal after setting up their team (FA, Maddon hire, etc.) for greater marketability?

JG: I don’t think these moves will affect much of anything when it comes to the TV deal. I suppose they don’t hurt, but if people paid to see a manager, the White Sox would’ve kept Ozzie.

I imagine the Cubs’ main argument in negotiations is you want to get in on the ground floor of a special run. The numbers from 03-08 are probably good evidence of that. Even so, I’m really interested to see the structure of this next deal. And where the games will land. Crane Kenney basically admitted they screwed up the last two deals, in that they turned out to be below market value. So now they’re gunning for big bucks.

TL: Where do you see them landing on TV?

JG: As a columnist I’m waiting. The next great outrage will be if fans can’t get half the games. Will the Cubs go back to WGN until the 2020 season?

Follow Jon at and @jongreenberg

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