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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2013 – RHP Phil Bickford (10th)

Notable players passed over: Tim Anderson (17th), Aaron Judge (32nd), Devin Williams (54th)

Another first-round pick blunder took place in 2013, as the Jays selected pitcher Phil Bickford out of Oaks Christian HS, California. Once again, the Jays failed to sign Bickford as he chose to go on to university baseball, despite being given an offer that was above slot value. This certainly presents the notion that there is always the risk in taking prep prospects, as the possibility of them not signing and going to college could be quite high, which has happened to the Jays twice in three years. The interesting thing of note was that the San Francisco Giants once again grabbed Bickford in the first round in 2015, so the Giants certainly have a thing for Jays’ missed first-round signings.

Bickford has gone on to have a somewhat up and down career so far in the major leagues, with one solid season with the Los Angeles Dodgers in 2021, followed by two sub-par seasons in the seasons up until now. But the real killer part for the Jays is that they missed out on MVP slugger Aaron Judge and electric closer Devin Williams. Judge goes without explanation what he could have provided for the Jays, as they probably would have avoided going into a full rebuild after 2016 if Judge was with the team already, as he made his big league debut in 2016 with the New York Yankees and has shone ever since.

In addition, even though it took quite the few years for him to fully develop in the Milwaukee Brewers’ minor league system, Williams’ emergence to dominance in recent years is exactly the shutdown flamethrower that the Jays desperately need right now. To add insult to injury, the Jays’ compensatory pick for not signing Bickford this time around became Max Pentecost, proving that lightning doesn’t strike twice, as this was a far cry from how we got Stroman from Beede’s compensatory pick.