Cubs: First-round shortcomings may have helped end the curse

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(Photo by Joe Sargent/Getty Images)
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The Cubs’ descent into baseball hell in the early 2010s and subsequent redemption in 2016 has become one of the iconic examples of “tanking” – the process of getting bad to get better. But Chicago was already pretty bad when Theo Epstein took over late in 2011, which made his tanking task easier.

The club was already bad, in part, because of a collection of largely unsuccessful first round draft picks over the previous decade. In the 10 years leading up to Epstein’s arrival, the Cubs made 14 first round picks (including four supplemental first-rounders). Let’s take a trip down this potholed memory lane to see how these picks may have inadvertently set the stage for the Cubs’ ultimate triumph.

The stats in this post all come from Baseball Reference unless otherwise noted. Player stats in bold are for their major league careers. Note that while the main point of this post is to call into question the Cubs’ first-round draft decisions in the pre-Epstein period, it’s also worth remembering that some of these players pancaked simply because baseball is really, really hard and most people who try it fail.

Of the 14 first-rounders, seven made the majors and five of those had careers lasting at least three years. For some context, two-thirds of first round picks signed from 1996-2011 reached the majors, and just under half had a career of at least three years. So the Cubs’ performance wasn’t woeful, but it was below par.

Chicago Cubs endure a first round drought: 2002-2006

From 2002 through 2005, the Cubs would draft a total of six first-rounders, none of whom reached the majors. These included four college pitchers in 2002 (Bobby Brownlie, Luke Hagerty, Chadd Blasko and Matt Clanton). Of these, only Brownlie would ever appear in a prospect top-100 list; he was Baseball America‘s #92 prospect in 2004.

Brownlie was also the the only one of the four to reach Triple-A, where he would post a cumulative 5.34 ERA across three different organizations. Clanton would only throw four professional innings, but unlike the few hitters he faced, he went down swinging.

In 2003 the Cubs drafted Ryan Harvey, who hit a Florida State League record four homers in one game for the Daytona Cubs in 2006. That was four more homers than he would hit in the majors; his lengthy minor league career would top out at Double-A. He finished with a minor league career strikeout-to-walk ratio of 4.5 to 1.

The Cubs drafted high-school right-hander Mark Pawelek, in 2005.  Pawelek is perhaps is most famous for this. Get outside kids: gaming kills. Even if Pawelek has pursued healthier habits, it’s unlikely he would have reached the majors. Wildness plagued his career; by the end he was putting the Dippin’ Dots vendors on base.

(Photo by Denis Poroy/Getty Images)
(Photo by Denis Poroy/Getty Images) /

Chicago Cubs find some modest first round success: 2006-2008

From 2006 through 2008 things improved, as the Cubs drafted five first-rounders, all of whom would reach the majors. Only Josh Vitters (drafted in 2007) would fail to have a three-year career. He stayed in the majors just long enough to accumulate 109 disastrous plate appearances in 2012, with an OPS+ of 7 for those of you keeping score at home. Among non-pitchers with at least 100 career plate appearances, that’s tied for the eleventh-worst career mark in major league history.

The most notable success story from this group has been Josh Donaldson, who is at 44.4 career WAR and counting. In a classic later-for-now trade, the Cubs sent The Bringer of Rain to Oakland for Rich Harden and Chad Gaudin in 2008. Harden would help the Cubs to finish first in the NL Central that year, but would be gone after the 2009 season. Donaldson, a late bloomer with an uncertain position, wouldn’t establish himself in the majors until 2012. It’s easy to look back in sorrow at this trade, but it made sense at the time.

The two other players to reach the majors in this period were right-hander Andrew Cashner and outfielder Tyler Colvin. Cashner would contribute little directly to the Cubs, but he was the key piece in the trade with San Diego that brought back Anthony Rizzo. So Cashner ended up being a key cog in the World Series machine, even though he was long gone by the time the curse lay bleeding.

Colvin was a power prospect who got his chance to start in The Show near the end of the 2009 season after right fielder Milton Bradley inexplicably decided to tell the Daily Herald exactly what he thought of playing for the Cubs.  Colvin went on to have a good year in 2010 until a grisly injury ended his season.  Although he made a “full recovery” he would never be able to tap into his power consistently. After a horrible 2011 the Cubs shipped him to Colorado, where he would have one more decent season before entering permanent decline.

(Photo by Lisa Blumenfeld/Getty Images)
(Photo by Lisa Blumenfeld/Getty Images) /

Chicago Cubs find Javier Baez, but little else in coming years

From 2009-11 the Cubs drafted three first-rounders, one of whom was Javier Baez, who you’ve probably heard some stuff about. Like, for example, that according to Stathead he’s the fifth-best Cubs shortstop ever.

The Cubs also drafted outfielder Brett Jackson (2009) and right-hander Hayden Simpson (2010). Jackson was a speedy, athletic centerfielder who, contrary to the stereotype of this sort of player, simply couldn’t make contact. He was done after 147 major league plate appearances, all but five with the Cubs, finishing with an epic strikeout rate of 40.8 percent that is lofty even by today’s incontinent standards.

As for Hayden Simpson, drafted in 2010, I see a hand raised in the back. Yes, Fangraphs?

The organization went out on a very thin, brittle limb when it took Simpson with the 16th-overall pick of the 2010 draft. Considered by most as a huge over-draft, the right-hander never really recovered from a nasty case of mononucleosis that caused him to lose about 20 pounds (and he wasn’t a big guy to begin with). His fastball reportedly sat in the low-to-mid 80s during while pitching this past season. A college draftee, Simpson will turn 23 towards the end of May in 2012 so time is not on his side. He didn’t get out of low-A ball in ’11 and might have to return there next season. — Marc Hulet, 2011

Simpson never made it to the majors. He was out of baseball by age 25, finishing with a career minor/independent league ERA of 6.83.

Some first rounders the Cubs could have drafted instead

Not only did the Cubs miss on most of the first-rounders they drafted, they also overlooked first-rounders still on the board who went on to have solid careers. Examples include:

  • Matt Cain (2002, LHP, 29.1 WAR) who went on to throw over 2,000 innings for the San Francisco Baseball Giants.
  • Aaron Hill (2003, SS, 24.4 WAR), who would have a good career with both bat and glove as an infielder, mostly with the Blue Jays and the Diamondbacks.
  • Jacoby Ellsbury (2005, OF, 31.2 WAR), who would finish his career with an 82.9 percent stolen base success rate, eighth-best for players with at least 300 steals.
  • Ian Kennedy (2006, RHP, 18.1 WAR), who would have his best years as a starter in his mid-20s with the Snakes, and eventually make a very successful late-career transition to the bullpen.
  • Jason Heyward (2007, OF, 39.4 WAR) who – and you kids won’t remember this – used to be a very good ballplayer. Before coming to the Cubs Heyward had only one season with a WAR below 3.6. Since his arrival at Clark and Addison, he has had no seasons approaching that level.
  • Christian Yelich (2010, OF, 33.4 WAR), who became a mainstay for the team that currently ranks as I-94’s best.

These are all first-rounders; the Cubs missed on later round gems, but so did just about every team. And the Cubs hit on some later round picks as well. But the first round is the most reliable route to big league success, and Cubs first round picks in the pre-Theo decade generally didn’t make the trip.

Next. Ranking the top free agent signings in Cubs history. dark

It’s possible that a better first round performance during this period would have prevented the Cubs from breaking the curse because the owners would not have felt the urgency to resort to the scorched earth practice of tanking. On the other hand, it’s also possible that Epstein would not have had to tank if he’d been able to take over a team less bereft of first round success.

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