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

Over the years, when it comes to making the right selection at the annual MLB draft, teams would have scouts, analysts, and others to help them decide who potentially are the best prospects to choose and develop from the draft. Despite extensive work put into each draft by team personnel, more often than not, getting the right prospect choice is a difficult task, with often a little luck coming into play as well. Nevertheless, it is important to hit with the first-round pick, because those players tend to have a greater chance of making an impact with their potential organization compared to those selected in the later rounds.

For the Toronto Blue Jays, they have been fortunate enough to draft some notable star players over the years in the first round, including Shawn Green, Shannon Stewart, Vernon Wells, Alex Ríos, Aaron Hill and the late Roy Halladay to name a few. But at the same time, they have also missed on quite a few, including the likes of Alex Sanchez, Augie Schmidt, Eddie Zosky, Felipe Lopez, Kevin Witt and others.

On the good side, the Jays have had some success in their most recent years, having drafted strongly in the first round with picks ending up as Nate Pearson, Alek Manoah, Austin Martin and Brandon Barriera. However, looking back in the past two decades dating back to 2000, there have been many big misses by the ballclub, which could explain some of the reasons why they weren’t a competitive team for the majority of the time aside from their playoff contending years in 2015 and 2016.

Here we take a look back at 10 of the worst first round draft picks selected by the Jays since 2000, and how their unfortunate selections led to more mediocre years for the ballclub than expected. The overall draft position of the player selected is shown in parentheses.

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2000 – OF Miguel Negron (18th)

Notable players passed over: Adam Wainwright (29th), Cliff Lee (105th), Yadier Molina (113th)

So you may be saying, “Miguel who?” Yes, exactly. Probably someone you never or anybody else has ever heard of or remember at all. Miguel Negron was an outfielder prospect selected by the Jays out of Manuela Toro High School in Puerto Rico. He would go on to spend his entire career in the minor and foreign leagues over 12 active years. He didn’t possess much power, nor did he hit for a high average, and never made it above Double-A during his tenure with the Jays’ organization. If you even try to just search his name, there isn’t any historical news about him to be found other than his playing stats. Hence, quite the sad pick for the Jays at the turn of the century when they were beginning to build their team around cornerstones Carlos Delgado, Doc Halladay and Chris Carpenter.

Unfortunately, with the Negron pick, the Jays missed out on star-caliber players such as Adam Wainwright, Cliff Lee and Yadier Molina. Wainwright or Lee would have been a tremendous addition to the Jays’ starting rotation, which was quite feeble behind Halladay and Carpenter. Molina would have automatically become the Jays’ mainstay backstop for the next decade, without worrying to have to go through the likes of Ken Huckaby, Tom Wilson, Greg Myers, Gregg Zaun, Rod Barajas and others as temporary stop-gap solutions. In addition, he would have been the ideal catcher to guide the young Jays’ pitching staff at the time with his game calling and most likely would have helped bring more productive years during Halladay’s tenure with the Jays.

2004 – LHP David Purcey (16th)

Notable players passed over: Huston Street (40th), Hunter Pence (64th), Dustin Pedroia (65th)

With the Jays’ history of rarely selecting a left-handed pitcher in the first round in MLB Drafts, they took that chance with David Purcey back in 2004, along with the following year in Ricky Romero, with hopes that they could become the next best homegrown lefty product since Jimmy Key. Romero certainly turned out alright as he would eventually become the Jays’ ace for a couple of years before the start of his downfall. But for Purcey, his window of fame was even shorter than that of Romero, as he would go on to have some underwhelming years with the Jays, with an ERA constantly over five, with exception to the 2010 season. Eventually, he was traded to the Oakland Athletics in 2011 in exchange for former Jays' farmhand Danny Farquhar.

In doing so, the Jays missed out on prolific closer Huston Street, who was selected 40th overall during the same draft. With the Jays constantly having an interchange of pitchers in the closer role during the 2005-2009 years, rotating between Jason Frasor, Miguel Batista, B.J. Ryan, and Jeremy Accardo, Street would have provided that long-term stability to close out games as he averaged almost 30 saves per season over an 11-year span between 2005-2015. Aside from Street, the Silver Slugger, MVP, and four-time All-Star Dustin Pedroia would have solved the Jays’ question mark at second base for at least a decade, providing the much needed mix of plus offence and defence at the position. But one could only wonder now how much different those Jays’ teams could have been if the right choice was made.

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.

2008 – 1B David Cooper (17th)

Notable players passed over: Gerrit Cole (28th), Jake Odorizzi (32nd), Lance Lynn (39th)

In 2008, the Jays took their chance on a University of California product with their first-round pick by selecting first baseman David Cooper. After the departure of superstar slugger Carlos Delgado following the 2004 season in free agency, the Jays never really had an adequate replacement at first base. Added to the fact that the 2008 MLB Draft was loaded with potential future star power at the first base position, with the likes of Eric Hosmer, Yonder Alonso, and Justin Smoak among those that were drafted even earlier than Cooper, who happened to be one of the better contact power hitters among the group. So it appeared that the Jays couldn’t really miss by taking one of them in the first round, or could they?

Well, Cooper progressed admirably through the Jays’ minor league system, while at the same time he hit for average, along with being a strong run producer. In 2010, he hit .257 with 20 home runs and 78 RBI with the Jays’ Double-A New Hampshire Fisher Cats, while in 2011, he did even better with the Jays’ Triple-A Las Vegas 51s, albeit with a little less power to show for, batting .364 with 51 doubles, nine home runs, and 96 RBI in 120 games played. In doing so, he eventually made his major league debut with the Jays that very same year. However, he was never able to translate his success from minor league ball to the major league level, as in another four years, he was out of the organization and out of baseball entirely by 2015.

The 2008 MLB Draft class also had an abundance of solid pitchers available in the first round, but the one the Jays really missed out on was the chance to get six-time All-Star and two-time Cy Young finalist and future ace Gerrit Cole. The only good part coming out of it was the fact that even though the New York Yankees took him with the 28th pick out of high school, they failed to sign him as Cole chose to attend college instead to further his development. As a result, he ended up going back into the draft and was taken first overall in 2011 by the Pittsburgh Pirates instead, keeping him out of the American League. Nevertheless, as fate was meant to be, Cole eventually made his way to the Yankees, so they still ended up getting him, just years later so that the Jays didn’t have to have an extended period of constant reminding of who they lucked out on.

2010 – RHP Deck McGuire (11th)

Notable players passed over: Yasmani Grandal (12th), Chris Sale (13th), Christian Yelich (23rd)

With one of their highest first-round picks in five years, the Jays selected Deck McGuire out of Georgia Institute of Technology, Atlanta. McGuire was the Atlantic Coast Conference Baseball Pitcher of the Year in 2009, as well as making the 2009 All-America Second Team by Baseball America, so he appeared to be a can’t miss pitching prospect. With Jays’ ace Roy Halladay no longer part of their starting rotation after the trade with the Philadelphia Phillies during the 2009-10 offseason, getting a prime starting pitching prospect from the 2010 MLB Draft seemed like a no-brainer.

Unfortunately, despite reaching the Triple-A level in the Jays’ organization by 2014, McGuire never really got a solid foot on the ground after producing unimpressive seasons in the minors, failing to live up to his full potential. Eventually, he was traded to the Oakland Athletics in 2014 for cash considerations. He did eventually make the big leagues in 2017 with the Cincinnati Reds, as well as a return stint with the Jays in 2018, but once again, he wasn’t able to perform effectively as a major league pitcher.

What has hurt even more is the fact that the draft picks just behind McGuire in 2010 were All-Stars Yasmani Grandal and Chris Sale, along with future NL MVP Christian Yelich. Any one of them could have been a huge difference maker for the Jays, especially Sale, since they were hoping to find a successor to Halladay at the time. And for a five-tool player like Yelich, let’s just say the Jays haven’t had the luck to unearth one in ages. Selecting McGuire probably set them back a few more seasons than expected, before their eventual rise to prominence in 2015.

2011 – RHP Tyler Beede (21st)

Notable players passed over: Kolten Wong (22nd), Trevor Story (45th), Blake Snell (52nd)

For the year 2011, this represented the second time in three years in which the Jays failed to sign their first-round pick. Not being able to do so is equivalent to having a wasted first round pick that year as if it never happened. But doing it two times in a span of three years could really hold back an organization for a while, especially for a team that was hungry and desperate in getting back into contending status, led by the hitting beasts José Bautista and Edwin Encarnación.

In the 2011 MLB Draft, the Jays went with pitcher Tyler Beede out of Lawrence Academy High School, despite knowing the fact that Beede was most likely committed to going to college already. The Jays took a big gamble, and lost badly as Beede went on to attend Vanderbilt University instead and was later taken in the first round in the 2014 MLB Draft by the San Francisco Giants.

By doing so, the Jays passed over future NL Gold Glover Kolten Wong, future Silver Slugger Trevor Story, along with future AL 2018 Cy Young winner Blake Snell in the process. That is quite the tough pill to swallow, but at least the Jays definitely felt a lot better when they happened to use their compensatory pick for not signing Beede on some unknown, upcoming bulldog prospect named Marcus Stroman in 2012. One would have to admit that luck was definitely on their side when they happened to land Stroman with their 22nd overall pick in 2012, but not every time one could be that fortunate, as can be seen a little later on our list.

2012 – OF D.J. Davis (17th)

Notable players passed over: Corey Seager (18th), Michael Wacha (19th), José Berríos (32nd)

Once again with another flopped pick in 2012, the Jays chose D.J. Davis out of Stone High School, Mississippi. The Jays were attracted to his speed and his potential in becoming a solid leadoff hitter in the future, something the team had lacked in their minor league system, after seeing the great job and effectiveness Rajai Davis had provided the team during the 2011 and 2012 seasons. D.J. Davis was ranked as high as fourth in the Jays’ MLB Top Prospects list in 2013, until he gradually regressed in the years that followed. He never managed to progress beyond the High-A level in the Jays’ organization and eventually was out of baseball entirely after the 2018 season.

This one kind of stung for the Jays, now knowing that there was a superstar in the making in just the pick that followed. That pick turned out to be none other than four-time All-Star, two-time Silver Slugger, and 2016 Rookie of the Year shortstop Corey Seager. If the Jays had Seager already in their system, there may not have been the desperate need to deplete quite a bit of their farm system to acquire the services of Troy Tulowitzki for their postseason runs in 2015 and 2016.

In addition, seeing the strong production put up by Seager in the past couple of years as well, he definitely would have been a major driver for the Jays’ offence, and could have very well been the power bat we have been desperately looking for to help the ballclub. Nevertheless, Seager is doing his thing with the Texas Rangers nowadays, but as an “okay” consolation, at least we got some shortstop named Bo Bichette doing his thing with the Jays currently as well.

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.

2016 – RHP T.J. Zeuch (21st)

Notable players passed over: Will Smith (32nd), Bryan Reynolds (59th), Pete Alonso (64th), Shane Bieber (122nd)

In 2016, the Jays took a shot at the product of University of Pittsburgh with their first-round pick of pitcher T.J. Zeuch. The name sure sounded powerful and unique enough, and most likely would have been a hit with the fanbase, as whenever he struck out a batter, one can coin the term and say they were “Zeuched”. He actually made some steady progress through the minor leagues and by 2019, he finally made his debut in the big leagues with the Jays, but would not end up sticking long with the team. His best season was in 2020 when he managed to get into three games in the COVID-shortened season and went 1-0 with a 1.59 ERA. However, following a sub-par 2021 season, he was eventually traded to the St. Louis Cardinals later that year for cash considerations, similar to the fate of McGuire in 2014.

Zeuch is currently with the Phillies organization, but appears to be far lower in the pecking order for reaching the majors once again in the near future. Looking back, the Jays missed out on some sure-fire prospects in catcher Will Smith, outfielder Bryan Reynolds, and first baseman Pete Alonso. Reynolds in particular has been rumoured previously as a projected target by the Jays during the past offseason, but apparently his asking price was quite high.

For Alonso’s sake, we will always remember him as the one that beat Vladdy in the epic Home Run Derby despite Guerrero setting the all-time record of 91 in the process. If looking down even further, there’s even Cleveland Guardians’ ace Shane Bieber with the 122nd pick, which could be a potential trade target right now for the Jays as they look to shore up their starting pitching. If we had the chance to get any one of them earlier, we wouldn’t have to ponder about trading for them now.