Cubs Conversation With MLB Network’s Mark DeRosa: “I Will Always Be a Cub”

Cubs Convention returns to Chicago this weekend accompanied by some buzz for the first time in a while. Most of the fanfare will be directed at the new shiny toys like skipper Joe Maddon and the even bigger offseason fish in Jon Lester.

Yet, the Cubs will also give some love to the past and the glory years. Yes, we will go all the way to back to those back-to-back divisional champs, as your 2007-08 Cubs will be celebrated.

On Saturday from 10:30-11:30 am a panel featuring former Cubs, some of whom have returned to the organization in some fashion, like Kerry Wood, Ryan Dempster, Henry Blanco, Ted Lilly, and fan fave Mark DeRosa will take the stage

I had a chance to catch up with DeRo not long ago and we talked about those years he spent in Chicago along with the future of the organization as he sees it from his MLB net analyst chair.

DeRosa waxed nostalgic about being back in Chicago.

“I love coming back here, man,” DeRosa said. “I really adopted it, the city and the fans really made me feel welcome. I loved it here and you’d be hard pressed to find a guy who played here in ’07 and ’08 who didn’t buy in and completely fall in love with being a Cub.”

After a lousy 2006 season, the Cubs rebuilt on the fly with a $300 million-plus spending spree at the Winter Meetings in Dec. 2006. They re-signed Aramis Ramirez, hooked the big free-agent fish Alfonso Soriano, and signed Ted Lilly, and utility man DeRosa.

“When I signed, I was a guy who still back in those early foolish days that was still reading everything written about him,” DeRosa said. “I remember the fans like saying ‘Who is this guy?’ and truly not knowing what I was about.

Why did that change so fast? Why did a player like DeRosa become so beloved so quickly?

“I think they bought into the fact I was a team guy, that I cared about winning,” he said.

DeRosa also gives much of the credit for his popularity to the fact that the Cubs had two very good seasons during his tenure in Chicago, seasons in which the organization took their best shot at winning the World Series.

“Obviously we fell short of what we wanted to ultimately give them,” he said. “At the same time we put a pretty good brand of ball there for two straight years.”

During the offseason following the 2008 campaign, then-Cubs GM Jim Hendry was trying desperately to land Padres pitcher Jake Peavy and also to add a bat in Milton Bradley. Hendry was newly limited with payroll flexibility, as Tribune owner Sam Zell prepared for a sale of the club.

Hendry had to make a sacrifice, so DeRosa was dealt to Cleveland for a package that included prospect Chris Archer. DeRosa was shell-shocked, as were most Cubs fans. Turns out Hendry couldn’t get Peavy, and the Cubs lost a great locker room presence, while gaining a clubhouse disaster in Bradley.

“I was so hurt personally when I got traded that you don’t want them to play well without you,” he said. “Even with being a part of eight different teams, I will always consider myself a Cub; those were the best two years of my career.”

I asked DeRosa if he could fully grasp how the Cubs went about tanking seasons in a full scale rebuild after experiencing the Cubs going full throttle when he resided here. DeRosa turned analyst in his assessment.

“You have to go one way or the other,” he said. “If you’re in the middle somewhere, where are you going? So either you got to go all in like we did in those years I was here, or you sometimes you got to try and rebuild. But you can only sell that to the fans for so long. At some point it’s going to be time to put a good product on the field. These fans are desperate for a winner. These fans deserve it. What gets lost in translation sometimes is that the fans are just going to show up. I think that’s unfair to assume.”

How important was it for the Cubs front office to add vets like Jon Lester, Miguel Montero, and Jason Motte for the young clubhouse?

“That is the thing, you were asking young players in their early 20s to carry a franchise; it’s not fair,” he said. “I couldn’t imagine that type of pressure put being put on me, there are growing pains. It’s amazing what these guys are able to do in the game, breaking in, hitting third and fourth in the order, being heads of a rotation. At the end of the day you have to have some veterans occasionally to steer you in the right direction.”

What is the next for the Cubs?

“The organization as a whole knows what they have to do,” he said. “I think they were waiting for the right time to make these additions. I think they were waiting for that moment.

Theo (Epstein) has done it before in Boston. He knows what it takes. He and Jed (Hoyer) have walked the walk. I knew they would strike when the time was right”.

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