The 10 best Blue Jays first-round picks in the MLB draft

Toronto Blue Jays' starting pitcher Chris Carpenter (26) is congratulated by catcher Alberto Castillo following Carpenter's 4-0 shutout of the Chicago White Sox on May 29, 2001. (Brian Kersey/AP)

We’re less than two weeks away from the start of MLB’s amateur draft. For a rebuilding team like the Blue Jays, this could mean a key milestone on the way to their next winning team…or a case of bitter disappointment.

Toronto picks 11th this year, following the team’s second straight sub-.500 season. Given the league’s checkered history of number-11 picks, that’s not an especially auspicious place to be.

For starters, the Blue Jays themselves have twice drafted from that spot. In 2010 they selected Deck McGuire, a right-handed pitcher who last appeared in the majors last season, and has delivered negative 0.2 Wins Above Replacement during his short big-league career. In 2014, the Jays again picked 11th, this time tapping Max Pentecost, a catcher who never made it to the Show, and recently announced his retirement.

We have seen a handful of stars emerge from the 11th spot, with Andrew McCutchen and Max Scherzer getting picked there in back-to-back years, and George Springer going 11th in 2011. Current Blue Jay Justin Smoak was also a No. 11, coming off the board to the Rangers in 2008. On the flip side, plenty of No. 11 picks have never made it to the big leagues, including a nine-year stretch from 1993 through 2001 in which just two players made the leap.

The Blue Jays’ own history of first-round picks is even more intriguing. Like every other franchise, it’s full of both booms and busts. To see how the Jays have fared over the years (especially when not picking 11th), we ranked the 10 best first-round picks in franchise history, as measured both by actual performance and also where each player was picked (a 28th overall pick who becomes a star is thus valued more highly than a No. 1 overall pick who becomes a star).

Here, then, is our all-time top 10 (picks made in the supplemental round after Round 1 don’t make the cut — sorry, Noah Syndergaard):

10. Ed Sprague (25th overall, 1988)

Career Wins Above Replacement: 5.7

By the numbers there are better candidates for this slot. But Sprague gets the nod for playing a key role on the World Series-winning teams of 1992 and 1993. Sprague’s game-winning, pinch-hit, two-run homer in Game 2 of the ‘92 World Series would’ve been enough by itself to sneak him into our top 10.

9. Marcus Stroman (22nd overall, 2012)

Career Wins Above Replacement: 11.5

With a resume that includes a top-10 Cy Young finish, several huge performances in big games, and a Toronto-embracing persona of a tattoo of the downtown skyline on his abdomen, Stroman has quickly become one of the most iconic pitchers in franchise history. Whether or not the current trade rumours ultimately lead to him getting shipped to another team, Stroman will leave a legacy Jays fans won’t soon forget.

8. Lloyd Moseby (2nd overall, 1978)

Career Wins Above Replacement: 27.5

Moseby would rank higher, but as the highest-drafted player on this list, he’ll settle for number-eight with a bullet. The Shaker teamed with George Bell and Jesse Barfield to form one of the greatest outfields of the modern era, the backbone of the first Blue Jays team to ever make the post-season. His 1984 season was especially beastly: 18 home runs, a league-leading 15 triples, 28 doubles, 78 walks, and 39 steals, to go with his usual solid defence in centre.

7. Vernon Wells (5th overall, 1997)

Career Wins Above Replacement: 28.5

Wells got derided for the massive contract handed to him by Jays management right before his production started to wane. But there’s a reason he got paid in the first place: Dude could rake. Wells hit .300 or better three times as a full-time player, with three seasons of 30-plus homers, amassing two top-25 MVP seasons, three All-Star berths, and one Silver Slugger to go with his three Gold Glove awards…all of that coming as a Blue Jay.

6. Aaron Hill (13th overall, 2003)

Career Wins Above Replacement: 23.7

A bat-first second baseman, Hill ran roughshod over the league in 2009, slugging 36 homers and knocking in 108 runs that season, good enough to bag an AL Silver Slugger award. Among 2003 first-round picks, only Nick Markakis has delivered more career value.

5. Shannon Stewart (19th overall, 1992)

Career Wins Above Replacement: 24.9

A fantasy baseball player’s dream, Stewart batted .300 or better six years in a row, and also stole 51 bases in 1998, his first season as a big-league regular. As productive as he was with the Blue Jays, Stewart finish fourth in MVP voting in 2003, after a mid-season trade to Minnesota led to him going hog-wild (.322/.384/.470) on the league.

Toronto Blue Jays Aaron Hill hits a foul ball against Chicago White Sox in 2011. (Chris Young/CP)

4. Alex Rios (19th overall, 1999)

Career Wins Above Replacement: 27.4

Rios would be a reasonable answer to the question, “Who was the last impact homegrown Blue Jays position player before Vladimir Guerrero Jr.?” The rangy right fielder looked like he might become a full-fledged star after making the all-star team in his third and fourth big-league seasons. Rios’s numbers tailed off after that, prompting a 2009 trade to the White Sox, where he found a second wind as one of the league’s best power-and-speed threats.

3. Chris Carpenter (15th overall, 1993)

Career Wins Above Replacement: 34.2

The most injury-prone player in our top 10, Carpenter underwent three elbow surgeries, two shoulder surgeries and one rib-cage surgery during his career, yet still persevered through 15 seasons and 144 wins in the big leagues. It would take an outright release by the Blue Jays and a new life with the Cardinals before Carpenter became a true ace, won who both a Cy Young award and an ERA title and finished top-three in Cy Young voting three times.

2. Shawn Green (16th overall, 1991)

Career Wins Above Replacement: 34.7

A steady hitter at the start of his Blue Jays career, Green really exploded on the league in 1999, when he batted .309/.384/.588, hammered 42 homers, drove in 123 runs, and led the league in doubles and total bases. His reward for that monster season was a trade to the Dodgers, where Green clocked two more 40-homer seasons, establishing himself as one of the most fearsome hitters in the league. Beyond all that, if there was a more coveted Toronto-area Bar Mitzvah guest in the late 90s than Shawn Green, we’ve yet to see him.

Toronto Blue Jays Shawn Green hits his three- run homer off Kansas City Royals starting pitcher Chris Fussell in the third inning during AL action at SkyDome in 1999. (Kevin Frayer/CP)

1. Roy Halladay (17th overall, 1995)

Career Wins Above Replacement: 64.3

One of two combatants for the title of greatest player in franchise history (Dave Stieb wasn’t as good in his prime but played a lot longer in Toronto), Halladay could rightly claim the title of Best Pitcher On Earth for at least a couple of years, with two Cy Young awards and seven top-five Cy Young finishes to back up that claim. An absolute workhorse who four times led the league in innings pitched, Doc became a legend both in Toronto and in Philadelphia, cementing his Hall of Fame career with his 2010 perfect game against the Marlins and a no-hitter that same year, in the playoffs against the Reds.

See you in Cooperstown this summer, friends.

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