How Clayton Kershaw Could Have Been a Pirate

For the second time in this 2020 World Series, Clayton Kershaw was dominant as he led the Dodgers to a Game 5 win over the Rays 4-2. However, Kershaw could have been in the Black and Gold had it not been for a draft goof-up.

When you think of Los Angeles Dodgers starting pitchers, one of the first names that come to mind is right-handed pitcher Clayton Kershaw. He was drafted seventh overall by the Dodgers in the 2006 MLB draft and has pitched for Los Angeles for the entirety of his 13 year Major League career. He has been a part of the MLB postseason in 10 of those 13 years and is having the best postseason of his career in 2020 going 4-1 with a 2.93 ERA. Some of his accolades so far include an NL MVP award, three NL Cy Young Awards, and eight NL All-Star Game appearances. He is the face of the Dodgers organization as they look for their first World Series Championship since 1988.

However, the entire course of his career could have been altered by none other than the Pittsburgh Pirates way back in 2006. The Pirates had the fourth overall pick that season, and many of their scouts had eyes on Kershaw as the man to go with. They invited general manager Dave Littlefield to see Kershaw pitch, and weather conditions affected the right-hander and he didn't have his best stuff. Littlefield was not impressed with what he saw and made the financial decision to not take Kershaw, since he would demand a lot of money for his signing bonus. Instead, Littlefield went with right-handed pitcher Brad Lincoln with the fourth overall pick in the 2006 draft.

Lincoln was a college arm that was a little more proven than Kershaw was, but wasn't nearly as talented. Of course, money played a big factor in the signing as Littlefield and the Pirates ownership knew that Lincoln would cost least than Kershaw. To this day, many experts still question the Pirate's decision and it turns out they were right. Kershaw has gone on to have one of the most successful pitching careers in Dodger's history, and Lincoln hasn't pitched in a Big League game since the 2014 season. Now, we never know what could have been if the Pirates would have gone with Kershaw, but his and the Pirates careers could have gone a whole lot differently.

Clayton Kershaw: Pittsburgh Pirates ace?

With Kershaw being drafted out of high school, and given the Pirates track record, he most likely would have started his career with either the Gulf Coast League Pirates or Bristol Pirates, as he did with the Dodgers. Right from the get-go, Kershaw showed dominance in the Minor Leagues, going 2-0 with a 1.95 ERA in 10 games, eight starts during the season. Given that success, his next move would have probably been full-season baseball in 2007. While the Dodgers started him in Advanced-A, the Pirates would have likely gone with Low-A West Virginia Power with a promotion to Bradenton by mid-season. Kershaw went 8-7 with a 2.95 ERA during 2007 and struck out an impressive 163 batters in 122 innings of work.

As we moved into the 2008 season, Kershaw would have most likely made the move to Double-A Altoona as part of the starting rotation. Kershaw ended up going 2-3 with a 1.91 ERA in 13 games at the Double-A level and held opponents to a career-low .179 batting average against. Now, this is where the two organizations differ because the Dodgers sent him to the Majors whereas the Pirates most-likely would have promoted him to Triple-A for the end of the 2008 season. As 2009 rolled around, the Pirates would have probably kept Kershaw with the Indianapolis Indians, possibly making him a September call-up that season. He more than likely would have made his first Opening Day roster in 2010 as a member of the rotation.

The Pirates had a few veteran hurlers as part of the rotation that season, as well as some young guys who were looking to make an impact. With names like Paul Maholm, Zach Duke, and Ross Ohlendorf on the team, the starting rotation probably would have looked something like this:

1. Zach Duke
2. Paul Maholm
3. Clayton Kershaw
4. Ross Ohlendorf
5. Jeff Karstens

Another starting pitcher, Brian Burress would have more than likely been sent to the bullpen in a long-relief role, replacing Brad Lincoln who wouldn't be on the team. 2010 was Kershaw's breakout year in the MLB as he went 13-10 with a 2.91 ERA in 32 starts while picking up his first career complete game. He would have been by far the best pitcher on the Pirates staff that season, with the next closest wins leader being Maholm with nine. He would have led the team in every statistical pitching category that season and could have given the team two rising stars with Andrew McCutchen starting to come into his own around the same time. Alas, the Pirates missed the opportunity and instead went with Brad Lincoln.

Brad Lincoln: 2006 Draft Bust

Instead of going with Kershaw, the Pirates ended up picking right-handed pitcher Brad Lincoln. It was hard to argue with Lincoln's talent, as he posted a 1.69 ERA and 12 wins during his senior year, but scouts projected him to go lower in the first round. He became the first C-USA player to be taken in the top 10 picks of the MLB draft and began his Minor League career. He also started in rookie ball during the 2006 season and rose through the Minor Leagues. He reached the Major League level by the 2010 season and began his career as a starting pitcher in the organization. He made his much-anticipated MLB debut on June 9th, 2010 against the Washington Nationals and things didn't go well.

He lasted six innings in the game, giving up five earned runs on six hits while walking two and striking out three in a no-decision. As the season moved on, Lincoln's outings weren't getting better. His best month came in June when he posted a 4.65 ERA, but he had an ERA over nine in each of his other two months pitched that season. The Pirates knew it was time for a change and sent Lincoln to the bullpen in 2012. This is where he finally came into his own, pitching to a 2.73 ERA in 59.1 innings of work. It was the best season of his professional career by far and bolstered his trade value. They ended up trading Lincoln to the Blue Jays that season for Travis Snider who provided a big boost off the bench for the team in the playoffs.

The Pirates may not have gotten Kershaw, but the plus is their window for the playoffs would have been about the same. One pitcher does not make a team and Kershaw definitely benefitted from the Dodgers organization. The Pirates are building towards having that competitive future and being able to be in the World Series hunt year in and year out. With Ben Cherrington at the helm, the draft is focused more on getting the best players possible and setting the team up for success now and in the future.

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