Six questions with Jon Lester

ESPNChicago.com’s Jesse Rogers has been doing “Five Question” interviews sporadically at Cubs camp this spring.  So I figured, “I’m better than Jesse.  I’ll do SIX question interviews.”

Today, the series starts with new Cubs ace Jon Lester.¹

How creeped out were you by the sweatpants wearing horde of Iowans at the Cubs Convention?

They were pretty intense.  We had some weirdos in Boston when I was there.  Basically, every woman over the age of 40 smokes six packs of cigarettes a day, and every guy is shirtless, wears his hat backwards and is named Sully.  The strangest thing about the Cubs fans at the convention was how aggressively nice they were.  One guy asked me to autograph his head so he could have my signature tattooed on his head.  It was Todd Ricketts.

You’re going to pitch on opening night and the bleachers will be empty because of the construction.  Is that going to be weird?

Hey, I spent the last two months of last season in Oakland where shit from the toilets backs up into the dugout.  I think I can handle a few empty seats.

When you signed with the Cubs you said you appreciated some of the little things Theo and Jed did during the process, like when they sent camo Cubs hats for your family.  Did other teams do similar things?

The Red Sox sent a huge poster-sized photo of me pitching in the 2013 World Series.  The Giants had Buster Posey show up at my house with a box of steaks.  The Marlins sent me a stripper.  I think his name was Gary.

The Cubs have been so bad for so long that players are saying the challenge of finally winning there is attracting them to the team.  Did that play a role for you?

People have these instincts that they try to pretend they don’t have.  It’s like when you drive by a car wreck and even though you don’t want to, you have to look.  I mean, you might see something horrible like a headless body or a motorcycle rider who’s now wrapped up in the axel of a big rig.  You know it, but you can’t look away.  The Cubs are basically the headless motorist lying dead on the highway, and you can’t not look at it.

Did the Cubs promise to bring David Ross in to be your personal catcher if you signed?

Actually, the sons of bitches promised NOT to bring him in.  That’s what I get for trusting Theo.

You played with Ryan Dempster in 2013 with Boston, and the Cubs hired him as a special assistant in the front office just before you made your decision to come to the team.  Dempster actively recruited you to the Cubs, did that play a role in your decision.

It played a big role, but I signed here anyway.  I mean, they offered $155 million dollars.  Even I can put up with Ryan Dempster for $155 million.

1. My legal counsel wants me to point out that it’s not really Jon Lester.  As if you thought it was.