I’m shocked that there is some suggestion that AA’s work to give the Jays at least a two year window wasn’t worth it just because they didn’t end up winning the World Series. Remember where the franchise was when he took over after JP Riccardi, it was a wasteland of talent and bloated contracts (Vernon Wells, Alex Rios etc.) and he slowly but surly rebuilt both the farm system and the MLB roster up with higher ceiling talent. He notably doubled the size of the scouting department to 54 in 2010 and it led to drafting talents like Aaron Sanchez, Marcus Stroman, and Noah Syndergaard. He also took chances on higher ceiling players that had fallen out of favour with their respective organizations like Yunel Escobar and Colby Rasmus and Brandon Morrow. Those players may not have been a part of the successful 2015/2016 teams, but they raised the talent level of the organization. He then made the famous deal with the Marlins which was a steal both at the time and in hindsight as none of the players that he sent to Miami have turned into anything while a guy like Mark Buehrle was a good veteran arm to both provide stability in the rotation and mentor the Jays young arms like Stroman. The R.A. Dickey deal looks bad in hindsight, and really it wasn’t great at the time either with Syndergaard a top 100 prospect (according to MLB Prospect watch, he was the #83 overall and the #2 prospect in the system behind Sanchez who was #38 overall and ahead of Justin Nicolino who was ranked 86th overall). I understood AA taking the shot on Dickey though, he was coming off of an NL Cy Young award and obviously presumed to be a top level arm, and he thought the team was going to be competitive after the Marlins deal and the thought of adding a top arm would be enticing. It didn’t work out as planned but every GM has those deals that they wish they could take back.
Next up was the 2014 offseason in which he learned the value of leadership and defence and it led to the signing of Russell Martin who has brought stability to the C position that the Jays lacked for soooooo long before. His contract hangs over them now, but he was a valuable part of the team success in 2015/2016 and still provides value with his glove. He then made the deal with Oakland that brought a future MVP talent to the team and changed the complexion of the organization from a pretender to a legit team. He then made then made the Tulowitzki deal with the Rockies which stabilized the middle infield defensively and gave us another power bat. David Price was acquired shortly after and while he didn’t perform in the playoffs, he was considered a true ace at the time and in theory gave the team a stud that they were missing beforehand. The result was a Blue Jays team that had a case as the best team in the league by far, as they paced the league in Run differential while having the toughest strength of schedule of any playoff team, a 1.6 Simple Rating system which was far and away the best in the league (simple rating system is the number of runs a team is better or worse than league average), and had the best Pythagorean win-loss record by far as well. The 2015 Blue Jays were an INCREDIBLE team and deserved a better fate, but that’s playoff baseball. Anthopolus left the organization that offseason after ownership brought in Mark Shapiro.
To put it another way, in 2008 the year before Anthopolus was hired (hired in the 2009 offseason), the Jays position players accrued 16.1 WAR and the pitchers accrued 23.3 WAR (51% of the WAR that year came from Halladay and Burnett on their own) for a total of 39.4 WAR.
In 2015 when he left the organization, the Jays position players accrued 35.8 WAR (7.2 WAR more than any other team) and the pitchers accrued 14.4 WAR for a total of 50.2 WAR.
Anthopolus added 10.8 WAR to the organization over his tenure plus gave the new management group a year of contention while having some interesting prospects leftover in the lower-levels of the system. The Jays were a joke when he started with dwindling attendance outside of Doc starts, and he made the team relevant again. He was a terrific GM and easily one of the best in the franchise history and his efforts were 100% worth the upper level exodus of prospects.