The year the Pittsburgh Pirates passed on Clayton Kershaw

In 2006 the Pittsburgh Pirates could have had Clayton Kershaw, so what went wrong?

There were a lot of reasons behind the Pittsburgh Pirates historic 20-year run without a winning season from 1993-2012. Some of it was due to money. Baseball’s refusal to implement a salary cap crippled small market clubs such as Pittsburgh. Poor management decisions also contributed. The Pirates were known to give out terrible contracts to players like Derek Bell and Pat Meares. That was money that could have been spent on younger, better talent.  Some of the losing also came from not being able to evaluate talent like Jason Schmidt.

The Bucs also were not known for getting the most back in exchange for the talent they could not keep, which was the case with the Aramis Ramirez trade.  As big a reason as anything else for their ineptitude, however, was the Pirates epic, almost annual failures in the MLB Draft.

Here are some notable examples of Pittsburgh’s draft misfortune.

1994: With the 11th pick, Pittsburgh selects shortstop Mark Farris, one spot ahead of future Boston Red Sock Nomar Garciaparra
1997: With the eighth pick, Pittsburgh Selects outfielder J.J. Davis, one spot ahead of future Minnesota Twin Michael Cuddyer
1999: With the ninth pick, Pittsburgh selects pitcher Bobby Bradley, one spot ahead of future Oakland A Barry Zito, two spots ahead of future Milwaukee Brewer Ben Sheets
2000: With the 19th pick, Pittsburgh selects pitcher Sean Burnett, ten picks ahead of future St. Louis Cardinal Adam Wainwright
2002: With the first pick, Pittsburgh selects pitcher Bryan Bullington, five picks ahead of future Kansas City Royal Zach Grienke
2006: With the fourth pick, Pittsburgh selects pitcher Brad Lincoln, three spots of ahead of future LA Dodger Clayton Kershaw.

As you could have predicted from the title, the last example will be the one that I talk about in detail in this article.

Everybody reading this piece should know the fate of the man the Pirates picked.

Every baseball fan in the world knows what happened to the man the Pirates should have picked. Lincoln became nothing more than a solid middle relief man, while Kershaw is already the greatest pitcher of our generation, and possibly on his way to becoming the greatest pitcher of all time.

So what led to the Pirates missing out on greatness this time?

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Clayton Edward Kershaw came from a long line of pitchers from the great state of Texas. You may have heard of Nolan Ryan and Roger Clemens. A native of Dallas, Kershaw showed his potential at Highland Park High School. One thing that Kershaw lacked, however, were physical attributes.

In an article for Bleacher Report detailing the Dodgers road to drafting what would become their face, Kershaw is described as a “skinny, stick figured high school kid.” In spite of that description, Kershaw was still highly regarded. Here is how breakdown of that first round by MLB.Com described Kershaw.

“Considered to be the top high school arm in the draft, Kershaw’s fastball sits in the mid-90s to go along with a big curve and workable changeup. An oblique injury hasn’t scared teams off.”

Brad Eric Lincoln, a fellow Texan who attended the University of Houston, was considered more polished coming in. In his last year with the Cougars, Lincoln posted an Earned Run Average of 1.69 and a WHIP of 0.96. 

The Pirates were pretty confident that they had gotten the real thing when they took Lincoln. In MLB.Com’s report on the selection, former Pirates scouting director Ed Creech had this to say.

“We saw nearly every one of his starts this year. We know what we are getting here. We’re very happy.”

Considering how Lincoln turned out compared to others in that draft class such as Kershaw, Andrew Miller and Max Scherzer, it might seem odd that Creech would say such a thing.

What the Pirates were getting turned out to be a man who would only start 22 games over three seasons with the team. A man who, although a solid middle reliever, would end up being shipped to Toronto in the midst of a pennant race in exchange for unproven outfielder Travis Snider, also a part of the ’06 draft as the 14th overall pick. Looking back at that quote from Creech, it’s easy to assume that he and the Pirates did not know what they were doing and/or were more worried about drafting cheap than drafting well. But pre-draft projections show that Creech was not alone in his praise.

In BaseballAmerica.Com’s mock draft, published on June 6, 2006, Lincoln was projected to go third overall to the Tampa Bay Rays. Kershaw, on the other hand, was set to go to the Detriot Tigers at number six.

If those projections held true, the Pirates would have been considerably better off, as a Long Beach State third baseman named Evan Longoria was slated to go at number four. The Dodgers, on the other hand, were projected to take another Texan in Kyle Drabek. I’ll go out on a limb and say that LA is happy they did not go down that path. Here is an excerpt what Jim Callis wrote for Baseball America in his mock draft. Interestingly enough, it appears that LA wanted what Pittsburgh ended up getting.

“Los Angeles had targeted Kershaw, the best high school player available. The Dodgers covet Lincoln and Longoria, but they won’t get this far. With extra picks, they’re in position to roll the dice on a high-risk, high-reward prospect, and in this draft, no one fits that description better than Texas high school right-hander/shortstop Kyle Drabek.”

Callis had this to say about Lincoln. Although this report of Lincoln isn’t the most positive, it does show that he was a prized draft prospect for teams that wanted an arm instead of a bat.

“For the second straight year, Tampa Bay’s scouting department may not get its wish. In 2005, Rays scouts wanted Andrew McCutchen or Cliff Pennington, but the former upper-management team mandated the selection of Wade Townsend, who blew out his elbow in the Arizona Fall League. This time, the scouts favor Longoria while the new regime wants a pitcher, either Lincoln or Washington righthander Tim Lincecum.” 

Next: Bucs Split Series With Marlins

So looking back on the pre-draft projections, it’s clear that passing on Kershaw for Lincoln was not a Moskos-Wieters situation. The Pirates picked Brad Lincoln because they felt he was the best player they could get their hands on, and as happens every draft, things did not work out that way.

The Major League Baseball Draft is not as celebrated that of the National Football League, but it is far more unique. In the NFL, virtually every player that gets his name called is from the college ranks. But in baseball, scouts and general managers have to decide between polished college players and high upside high school kids, and as this draft shows, that is not an easy thing to do.