The Chicago Cubs haven’t won a World Series since 1908, and it doesn’t look like the Major League Baseball team will break that streak this season.

Behind the scenes, the Cubs’ front office is working on turning around more than a century of misfortune. One of the people directly responsible for how the Cubs will play in the future is the guy who makes the picks on draft day — Cubs scouting director Tim Wilken. In 32 years in baseball, with the Toronto Blue Jays, Tampa Bay Rays and Cubs, Wilken has been directly associated with the drafting and/or signing of eventual major league players, such as Chris Carpenter, Carlos Delgado, Roy Halladay, Vernon Wells, Michael Young and Jeff Niemann, as well as former Hawks Tyler Colvin and Andrew Cashner.

Idaho Press-Tribune Sports Editor Tom Fox talked with Wilken during his recent visit to Boise to see the Cubs’ shortseason Class A Hawks in action.

IPT: From the outside, it looks like you really like well-rounded athletes and guys with a good background, a winning background.

TW: First preference (is) middle of the field — catcher, pitcher, short, center. If I had my druthers, I’d rather take those players first, rather than the lug or the corner guy. I’ve had a special feeling for those guys, plus a lot of those guys in the middle can end up playing other places for your club, such as guys like Casey Blake — Ryan Freel played everywhere — and Michael Young. A lot of those guys could go play other positions. They weren’t limited, they were winners, and winners in life. It resonates all around the clubhouse when people say, “that guy plays like a winner, I want to be like that guy.”

IPT: Is that something more and more that you guys, the Chicago Cubs, are trying to get out of the draft, because it’s been awhile since the big club has won a World Series.

TW: I think so. That’s always been the key for me growing up and in the scouting world. Guys like Pat Gillick ... they talked about those ingredients being the winning part of it. I’ve just held on to those thoughts. I think it’s paid off pretty good. We try to employ it here. ... (Matt) Szczur, (Austin) Kirk and Pierre (LePage), those guys are winners. They make the people around them winners.

IPT: If you look at today’s lineup with the Cubs, what are some of the immediate needs that need to be addressed, and can you eventually see some younger guys filling in?

TW: I think we’re getting to the point in this organization where we can go get guys now. It may be a year away, but we can go get some catchers now, we can get some middle infielders, we can get some outfielders, we can get some pitchers, both right and left handed. Hopefully, we can develop some left-handed starters. I think we’re starting to put that picture together.

IPT: You already have two players from your first draft with the Cubs (2006) who have made the major leagues in Tyler Colvin and Jeff Samardzija. Andrew Cashner from your third draft has already made the major leagues.

TW: We’ve got one from our second one, we’ve got (James) Russell, (Josh) Donaldson’s with Oakland. It looks like we have a chance for maybe (Matt) Camp or (Darwin) Barney. It’s looking up. We’ve had decent fortune, and I think there’s some other guys coming along, too.

IPT: You surprised some people taking Colvin 13th overall in 2006, just like you did with this year’s first-round pick.

TW: Yeah, I heard, “you should have taken this guy or that guy.” Now, it seems like he’s passed up a few of those guys. I was used to it. I was in situations in Toronto where we didn’t have any money and we had to improvise. Vernon Wells and (Alex) Rios weren’t big on boards and some people questioned it at the time, but over time, eventually, they proved they were pretty good players. I think Tyler has a chance to do that. We think the same way about (this year’s top pick Hayden) Simpson. He wasn’t the darling of the prognosticators, but, hey, you gotta go with what you feel at the time. You think they’re a front-liner and winner, and that’s what I thought with those players. That’s what I think with Simpson, too. That’s what I thought with Cashner, (Josh) Vitters, all those guys. We’ll see if we’re right or wrong. Meanwhile, we have to find some guys to help us win in Chicago and win the big one.

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