The Pittsburgh Pirates Passed on Clayton Kershaw in 2006

The Pittsburgh Pirates have had their fair share of problems drafting and developing players.  This was especially true back during the early 2000s.

The Pittsburgh Pirates are not a very good team right now.  This past season was a tough year, the team finished with the worst record in the league, and they have been trending in this direction since the 2016 season.  One reason the team is struggling right now is because the lack of success in drafting and developing players.  Clayton Kershaw could have been, and probably should have been, drafted by the Pittsburgh Pirates.  Instead, Kershaw is hunting an elusive World Series with the Dodgers.

While this has been an issue in recent years, this was an even bigger issue back during the early 2000s.  At the time, Kevin McClatchy owned the Pittsburgh Pirates.  He employed Dave Littlefield as the team’s General Manager.  These are two of the names that will always been connected to the demise of the Pittsburgh Pirates franchise.

McClatchy, was even more shrewd of an owner than Bob Nutting, and was very conscious about the team’s budget.  In the same breathe, Littlefield folded and adopted this philosophy and built his team and organization by prioritizing the budget first.  However, this did not just include being financially conservative at the big league level.

Littlefield often did not take the best available prospect on the board.  When he was the General Manager, Major League Baseball did not have the financial restrictions they currently have on draft bonuses.  Players had a lot more power then, they could negotiate a higher price if they wanted, or choose not to sign with that team and try to get more money the following year.  Today’s MLB Draft model makes this a much riskier decision.

Dave Littlefield and the Pittsburgh Pirates often considered other factors than just overall talent. Money, or signability, was often the primary factor.  A prime example of this would be the 2006 Amateur Draft. The Pittsburgh Pirates had the fourth overall selection, a spot that a team would hope to land a future All-Star.

The Pittsburgh Pirates saw Evan Longoria go third overall to the Tampa Bay Rays.  This was after Luke Hochevar and Greg Reynolds went at number one and two respectively.  The Bucs knew they wanted to add a pitching prospect, but had to make decision on a prep player or a college player.

The story goes that the Pittsburgh Pirates scouts loved what they saw from Kershaw, who was widely regarded as the top prep pitching prospect in the country.  Many scouts, including the Pittsburgh Pirates scouts, loved his upside.  Apparently, the Pirates scouts were all in agreement that Kershaw should be the pick at number four.

Finally, the Bucs scouts convinced Dave Littlefield to take a trip out and watch Kershaw for himself.  Littlefield made a trip to watch Kershaw pitch.  The conditions of the game were very poor, with cold temperates and precipitation.  Not in any way ideal for a pitcher, let alone a high school arm.  Naturally, Kershaw did not have his best stuff, and in turn, left Dave Littlefield underwhelmed.

This was the one and only time that Dave Littlefield saw Kershaw pitch.  Back then especially, prep players had a lot more negotiating leverage.  Littlfield, who prioritized the financial side of things, saw everything he needed to not take the financial risk in Kershaw.  With Kershaw being considered the top prep pitcher, he would get whatever bonus he demanded.  Littlefield did not want to take the chance that they would not be able to meet Kershaw’s asking price, and if they did that, he was not getting a player that he believed in.

So instead, the Bucs went the safe route and drafted a college arm.  The team took University of Houston pitcher Brad Lincoln.  Lincoln was viewed as a first round talent, although many questioned the Bucs taking him at number four overall.  Littlefield took Lincoln at number four because he knew he would get a player who would reach the big leagues and they would not have to overpay to get him.  This is just one of the many mistakes Dave Littlefield made in his time here as GM.