Draft preview: Cubs not afraid to take risks

Many thought the Cubs reached when they selected Clemson's Tyler Colvin in the first round of the 2006 draft. Scott Cunningham/Getty Images

Chicago Cubs scouting director Tim Wilken has always been an out-of-the-box thinker when it comes to the draft. In 2006 Wilken selected Tyler Colvin, a skinny Clemson outfielder in the first round, a pick that was much maligned by the scouting experts, who usually rank the draft.

Colvin was ranked 170th at the time by Baseball America. In following years, Wilken chose third baseman Josh Vitters in 2007, power pitcher Andrew Cashner in 2008 and outfielder Brett Jackson in 2009. Cashner and Colvin already at the big-league level. Vitters and Jackson could be making an impact on the North Side by 2011.

Let's take a look at possible No. 1 picks by the Cubs, who draft 16th in the three-day draft that begins Monday.

Right-handed pitcher Karsten Whitson out of Chipley, Fla., had a bit of a rough 2010 season. But he still ranks 15th overall in Baseball America's Top 100 amateur players. Whitson, 6 foot 3 and 185 pounds, is ranked as the second-best high school pitching prospect behind only Jameson Tallion out of Woodlands, Texas.

The other possibility that Wilkenhas been toying with is drafting high school catcher Justin O'Connor from Muncie, Ind. That could be the direction the Cubs go.

Wilken is not afraid to draft a high school player who might take three to five years of developmental time. Wilken was the one who drafted Roy Halladay out of high school when he was the scouting director for the Toronto Blue Jays.

"We saw him early that year and he was impressive," Wilkensaid. "But as a final test we had him do some endurance running with a couple of the other guys who were going to be drafted high. Halladay held up when the others didn't. Other pitchers were projected higher in that draft. We looked at every physical and makeup scenario before we made that pick."

Wilken also saw some raw tools and makeup in Colvin before he chose him in 2006. Colvin's sudden power surge in the offseasonof 2009 has him on the cusp of being an everyday outfielder with the parent club.

"We always liked his swing," Wilkensaid. "He wasn't able to lift weights for the last three years. He had the arm problem [Tommy John surgery after 2008]. Now that the arm problem is behind him and he has gotten with [trainer Tim] Buss, you saw the results. He was always a good low-ball hitter, and when the ball came off his bat, even when he was younger, it came off pretty special."

If Colvin becomes a starter, he along with Starlin Castro will be the first two rookie position player starters from their system since 1989 when Jerome Walton and Dwight Smith were 1-2 in Rookie of the Year voting.

The projected pick here is O'Connor.