Ten Best Chicago White Sox First Round Draft Picks of the last 40 Years



June 10 brings the Major League Baseball draft, an event that is “hit-or-miss” to say the least. Draft position, like recruiting rankings, can just as often be an indicator of future success as it is future failure. The only thing it absolutely predicts 100% is sky-high expectations.

Let’s look at 10 of the best and 10 of the worst first round draft picks for both the Chicago Cubs and the Chicago White Sox. Yes, we know that listicles are to journalism what Taco Bell is to food. However, it also worth noting that Taco Bell measures its annual revenue in the billions.


Side note, go here for the 2020 MLB Draft mock sourcing for the Chicago Cubs and the Chicago White Sox.

See Also:

10 Best Chicago White Sox First Round Picks of the Last 40 Years

10 Best Chicago Cubs First Round Picks of the Last 40 Years

10 Worst Chicago Cubs First Round Picks of the Last 40 Years

10 Worst Chicago White Sox First Round Picks of the Last 40 Years

1. Frank Thomas, 7th overall, Auburn, 1989

No-brainer as he’s right up there with Shoeless Joe Jackson as arguably the best player in White Sox history, and without a doubt the team’s best player of the past half-century. He’s also the only White Sox first round pick to reach the Hall of Fame or win the MVP award.

chris sale

2. Chris Sale, 13th overall, Florida Gulf Coast University, 2010

All that he accomplished in White Sox pinstripes is very well documented. When he changed his Sox to red in 2017 Chicago got a lot back for him. Remember, this list is all about return on investment so if Yoan Moncada and/or Michael Kopech ever develop into all that they can be, then he’ll…..

…oh, wait, he’s already #2 and nobody is surpassing the Big Hurt, so never mind.

chris sale sox pitching prospect

Will Sale help the sox “Sail into October/”

3. Gio Gonzalez, 38th overall, Monsignor Edward Pace High School, 2004

His glory days have been in a uniform that does not say White Sox, but the team was able to get Jim Thome in return for him. Thome, in addition to being the nicest star professional athlete that you’ll ever meet, gave the Southsiders three exciting seasons, one of which included his 500th home run, and another that featured his game 163 winning homer.

4. Jack McDowell, 5th overall, Stanford, 1987

The only Sox first round draft pick to ever win the Cy Young award, “Black Jack” was a three time All-Star who has also been a professional musician, with the rock bands The View and Stickfigure.

5. Robin Ventura, 10th overall, Oklahoma State, 1988

Two All-Star game berths and six Gold Glove awards gets him the #5 spot

6. Alex Fernandez, 4th overall, Miami Dade College 1990

Look at this run of four consecutive first round draft picks!! You’ll never see any team draft that well/get great fortune with four picks in a row like this ever again.

Fernandez was inducted into the Hispanic Heritage Baseball Museum Hall of Fame in 2008.

7. (tie) Daryl Boston (7th overall, Woodward High School, 1981), Aaron Rowand (35th overall, Cal State-Fullerton, 1998) 

Two serviceable, mediocre outfielders, the latter of which was vastly overrated by White Sox fans because he played extremely ballsy and won a World Series with the team in 2005.

8. Ron Karkovice, 14th overall, William R. Boone High School, 1982 

Offensive numbers are blah, but underrated player who brought it defensively and added a lot to the clubhouse. Decent player who was always overshadowed by Carlton Fisk.

white sox

9. Carlos Rodon, 3rd overall, NC State, 2014

This season’s opening day starter, on May 13 it was announced that the poor guy would undergo Tommy John surgery and be out for the remainder of the 2019 season. So far, he’s put up kind of serviceable at best, meh at worst numbers, but here’s to hoping he comes back stronger and someday lives up to his lofty potential. 

10. Three headed monster of mediocrity Kip Wells (16th overall, Baylor, 1998), Jim Parque, 46th overall, UCLA, 1997), Rocky Biddle

Wells certainly had his moments, Parque was decent for a bit, and sometimes Biddle added something to the rotation, sort of kind of. However, you can’t really say that any of this triad was anything special in the bigger picture, and instead of just picking one (which would be Kip if we had to), we put the whole troika of meh in the final slot.

After all, 10th isn’t all that great spot anyway.

Honorable Mention: Harold Baines, a six time All-Star who fell only 144 hits shy of the magical 3,000 mark was the 1977 overall top pick. Unfortunately though, our list begins in 1980.

Getting There:

Tim Anderson, 17th Overall, East Central Community College, 2013 

The good news is he’s an everyday starter, the bad news is well: in 2017 he batted .257/.276/.402, walked in 2.1% of his at bats (the lowest percentage in the major leagues), and had the lowest walks-per-strikeout ratio in the majors (0.08). On defense, he led the major leagues in errors, with 28.

In 2018 he batted .240/.281/.406. On defense, he tied for the major league lead in throwing errors, with 12. 

Last season he won the AL batting title!

Paul M. Banks runs The Sports Bank.net, which is partnered with News NowBanks, the author of “No, I Can’t Get You Free Tickets: Lessons Learned From a Life in the Sports Media Industry,” regularly contributes to WGN TVSports IllustratedChicago Now and SB Nation.

You can follow Banks, a former writer for Chicago Tribune.comon Twitter and his cat on Instagram.

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