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

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Monday night 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. Between now and Monday we’ll look at the 10 best and 10 worst first round picks for both the Chicago Cubs and the Chicago White Sox. And 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.

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Results vary when it comes to the future careers of first round MLB Draft picks. It’s as unpredictable as the ultra hot deluxe, an exciting online slot game with blazing rewards. Anything can happen, and you can just as easily jackpot as you would bust. Have issues with the rankings on this list and/or snubs from it?

Of course you do. That’s what the comments section is for. Side note, go here for 2019 MLB Draft mock sourcing for the Chicago Cubs and the Chicago White Sox.

1. Kris Bryant, 2nd overall, University of San Diego, 2013

He’s just 27, so much if not most of his story is yet to be written, but he already has a World Series ring, NL MVP and NL Rookie of the Year award to his credit.

No other Chicago Cubs first round pick can claim that, so case closed on who is #1.

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2. Kerry Wood, 4th overall, Grand Prairie High School, 1995

You might remember Woodie for his injuries, and how that kept him from all that he could have been, but you really shouldn’t. Kid K won the 1998 Rookie of the Year Award, a season where he broke the single strikeout record.

He also loved the Chicago Cubs so much that he left a ton of money on the table in order to come back to the club in 2011. As both a starting pitcher and as a closer, the two time All-Star can arguably be defined as the modern day Mr. Cub.

3. Javier Baez, 9th overall, Arlington Country Day School, 2011

Have you seen this dude play lately?

The 2016 NLCS co-MVP and NL leader in RBIs/Silver Slugger/All-Star is tearing it up

4. Joe Carter, 2nd overall, Wichita State University, 1981

Obviously he’s known first and foremost for his World Series heroics with Toronto, and secondarily for the big numbers he put up in Cleveland. However, the Cubs did get Rick Sutcliffe in return for Carter when they traded him to the Indians, and Big Red was instrumental in making the 1984 magical.

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5. Andrew Cashner, 19th overall, TCU, 2008

Was traded for Anthony Rizzo; enough said. Remember this ranking is largely about ROI.

6. Rafael Palmeiro, 22nd overall, Mississippi State University, 1985

A member of the 3,000 hit and 500 home run club, albeit obviously aided by illegal performance enhancing drugs. Additionally, Palmeiro was about as bad as lying about using PEDs as anybody in the steroid era. He apparently doesn’t have much to do these days, as he, alongside his son, were playing for the Sugarland Skeeters, an independent league team last season.

Both had planned on coming back this season, but were released a couple weeks ago. At age 54, Palmeiro wasn’t able to recover well enough from knee surgery to full contribute.

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7. Shawon Dunston, 1st overall, Thomas Jefferson High School, 1982

Did he live up to his hype?

No, but he was the only #1 overall pick in Chicago Cubs history. Was his plate discpline atrocious?

Yes, but he still provided a whole lot more production for the club, and thus Return on Investment than most of the club’s first round picks in the past three decades.

7. Albert Almora, 6th overall, Mater Academy Charter School, 2012

Has some limitations as a player, and sorely lacking in power, but a .284 lifetime hitter, with most likely a bright future ahead is certainly worthy of a top ten place.

9. Kyle Schwarber, 4th overall, Indiana, 2014

Definitely ranking him way too high, but 1.) we’re still crazy enough to believe he’ll someday fulfill his potential and 2.) his value to the organization isn’t fully reflected by his on the field stats as his RUTHIAN DINGERS, SCHWARBOMB!!! SCHWARBLAST!!! provide a lot of fun and hence marketing value to the Chicago Cubs.

10. Mark Prior, 2nd overall, USC, 2001

You might remember him for his injuries, and how that kept him from all that he could have been, but don’t let that overshadow how dominant he was, albeit very briefly, at the Major League level when healthy. And while he’ll never be in Cooperstown, he is literally in the finest art museum you’ll find…in the state of Arkansas.

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Worth noting: Doug Glanville, Corey Patterson

The former is now known for his media career (like when the Cubs went overtly Draconian on some idiot nobody for flashing a white power sign at him earlier this month, obviously wagging the dog on Addison Russell promotion day), but don’t forget his 2003 NLCS heroics.

As for the latter, well he was just never lived up to the hype, but hey at least he made it to the MLB level to be a bust. A lot of Chicago Cubs first round picks fell well short of that.

Paul M. Banks runs The Sports Bank.net, which is partnered with News Now. Banks, the author of “No,  I Can’t Get You Free Tickets: Lessons Learned From a Life in the Sports Media Industry,” regularly appears on WGN CLTV and co-hosts the Let’s Get Weird, Sports” podcast on SB Nation

Banks, a former writer for NBC Chicago.com and Chicago Tribune.com, also contributes to Chicago NowFollow him on Twitter and Instagram. The content of his cat’s Instagram account is unquestionably superior to his.

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