Anthopoulos’s best and worst moves as Blue Jays general manager

R.A. Dickey stands with then-Blue Jays GM Alex Anthopoulos at his introductory news conference in Toronto on Tuesday, January 8, 2013. (Chris Young/CP)

When Alex Anthopoulos’s time as Toronto Blue Jays GM came to an end in the fall of 2015, it was easy to see him returning to the same post with a new team before too long.

After a couple years working in the Los Angeles Dodgers front office, Anthopoulos is back in the big chair, taking over as GM of the prospect-rich Atlanta Braves.

A native of Montreal, Anthopoulos was just 32 years old when he became general of the Blue Jays right before the end of the 2009 season. His tenure with the Jays was initially marked by rebuilding a depleted farm system, but Anthoploulos also showed a willingness to push his chips in the middle when he felt it critical to do so.

Some moves in Toronto had people hailing him as a genius, while others aged poorly. With that in mind, here are a half-dozen examples of Anthopoulos’s best and worst work.

[snippet id=3305549]

The Best

Make it rain

What a heist it was acquiring Josh Donaldson from the Oakland Athletics in December of 2014. From the moment Donaldson hit the diamond with Toronto, it was clear the club had its best position player since Roberto Alomar (with exception to perhaps Carlos Delgado). Donaldson won American League MVP honours during his first year with the Jays and remains one of the top power threats in the game.

Trade deadline, 2015

What a dizzying few days that was. Believing his 50-51 club had the potential for much better results, Anthopoulos pulled the trigger on a trade with the Colorado Rockies for shortstop Troy Tulowitzki on Jul. 28, then landed pitcher David Price from the Detroit Tigers in a three-team swap on Jul. 31. What happened next was well worth the prospects surrendered, Tulowitzki’s increasingly onerous contract and the fact Price left the team three months later as a free agent (which may be good thing).

Beyond the tangible gains of putting Price and Tulowitzki in the lineup, there was enormous symbolic meaning for Toronto, which had spent two decades producing completely uninspiring results. Jays fans turned out in droves to the Rogers Centre to watch their team run away with the A.L. East and compete in the American League Championship Series for the first time since 1993.

Sign here, Jose

When Anthopoulos inked Jose Bautista to a five-year, $65-million pact late in the winter of 2011, the slugger was coming off an out-of-the-blue 54-homer season in 2010. Baseball history is littered with guys who slugged the lights out for a season, then retreated back to obscurity. The value Bautista provided the Blue Jays as a deadly bopper over the course of the deal surely exceeded what even Anthopoulos hoped for.


The Worst

Winter, 2012

Anthopoulos made a big-time splash three years into the job when he acquired freshly minted N.L. Cy Young winner R.A. Dickey from the New York Mets, as well as flashy shortstop Jose Reyes and pitchers Mark Buehrle and Josh Johnson from the Miami Marlins. The moves were designed to make the Jays instant contenders, but the club scuffled out to a 10-21 start and — with the exception of an 11-game winning streak that provided some false hope — never got untracked.

Making matters worse, Noah Syndergaard — surrendered in the Dickey deal — has shown the potential to be one of the best pitchers in baseball.

Trading a legend

In fairness to Anthopoulos, he’d barely been on the job a month when he was tasked with trading the face of the franchise, Roy Halladay, to the pitcher’s preferred team, the Philadelphia Phillies in December, 2009. A return based around pitcher Kyle Drabek looked solid at the time, but history has not been kind to this deal. The one player Toronto got in the package who has looked solid catcher is Travis d’Arnaud, but he was flipped to the Mets in the Dickey swap.

Gone Gomes

Though by no means a franchise-breaker, Anthopoulos whiffed when he moved catcher Yan Gomes with infielder Mike Aviles to the Cleveland Indians for pitcher Esmil Rogers just a few days into the 2012 off-season. Rogers disappointed in Toronto, while Gomes — when healthy — has been a solid contributor to very good Cleveland clubs.

When submitting content, please abide by our submission guidelines, and avoid posting profanity, personal attacks or harassment. Should you violate our submissions guidelines, we reserve the right to remove your comments and block your account. Sportsnet reserves the right to close a story’s comment section at any time.