Toronto Blue Jays: The 10 worst first-round picks since 2000

Which former Blue Jays' first-round draft picks do they regret taking over the past 23 years?

Toronto Blue Jays v Oakland Athletics
Toronto Blue Jays v Oakland Athletics / Michael Zagaris/GettyImages
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2007 – SS Kevin Ahrens (16th)

Notable players passed over: Todd Frazier (34th), Sean Doolittle (41st), Josh Donaldson (48th)

In 2007, the Jays received a valuable compensatory first-round pick that slotted them in the middle of the first round when they lost free agent Frank Catalanotto to the Texas Rangers during the offseason. The pick was even higher than their own at number 21. So to fully take advantage of the extra high pick, they selected shortstop Kevin Ahrens out of Memorial High School in Houston, Texas. At the time, the Jays had the likes of John McDonald, David Eckstein, and Marco Scutaro manning the shortstop position at the big league level and they were definitely not long-term solutions for the team. Ahrens was projected to be a plus power, switch-hitting infielder with a great arm, so great that they decided to groom him through the third base position as well, as he was being compared to the likes of Hall of Famer Chipper Jones.

However, Ahrens failed to reach his full potential, becoming a career minor leaguer and never was able to progress beyond Double-A ball. The Ahrens pick led the Jays to missing out on future solid MLB players in Todd Frazier and Sean Doolittle. But the one that stood out the most was the player selected 48th overall, who happened to be the “Bringer of Rain” himself Josh Donaldson. The fortunate part is that the Jays eventually still got Donaldson in the end, and at the right time in his prime later on via a blockbuster trade with the Oakland Athletics in the 2014-15 offseason. The bad part is if they had Donaldson earlier, their contention window may have opened way earlier, instead of just for the two years in 2015 and 2016.