Five strategic turning points of Alex Anthopoulos' tenure as Blue Jays general manager

With an official press release and a teleconference, the book is now closed on Alex Anthopoulos's six-year run as general manager of the Blue Jays. While relatively short, his tenure was packed with huge moves, so let's take a look through the major twists-and-turns that led us to where the franchise is today.

1. Investing in amateurs and re-orienting the focus

Under predecessor J.P. Riccardi, the Blue Jays had radically overhauled the way they brought amateur talent into the system, focussing on "safer" college players while largely eschewing "riskier" high school players and retrenching from the international free agent market that had long been a pipeline of talent. The Jays were one of the lightest overall spenders in both markets, despite a lack of spending restrictions and they reduced the number of scouts employed. The result was that after eight years, Toronto had failed to build a homegrown core of talent, and had one of the worst minor league systems in baseball.

Anthopoulos immediately changed that, expending the amateur and professional scouting staffs, and aggressively spending on both areas while focussing on high upside, impact talent even if it was riskier and required higher bonuses above the recommended slots. He also exploited the system to accumulate extra high picks. In total, in 2010-11 he spent around $40-million in bonuses for amateur talent in the last two uncapped spending years. This compared to around just $12-million in the two years before that.

The results were dramatic. Despite missing on Deck McGuire at the top of the 2010 draft, it will go down as one of the best in Blue Jays history, producing Aaron Sanchez, Noah Syndergaard and Justin Nicolino before the second round was done, as well as useful players Sam Dyson and Sean Nolin lower down. In the 16th round, they stole Dalton Pompey (and two rounds later picked Kris Bryant though couldn't convince him to sign).

The 2011 draft was considered deep and the Jays had acquired had a ton of picks, yet the results were more mixed with a number of misses at the top. Still, they got Daniel Norris in the second round, and found more talent later down: Anthony Descalfani in the sixth round and Kevin Pillar in the 32nd round. And of course not signing Tyler Beede gave them the 2012 pick that netted Marcus Stroman.

But the 2011 international class is the stuff of legends: Roberto Osuna, Miguel Castro, Alberto Tirado, Jairo Labourt, Wilmer Becerra and Jesus Tinoco, many of whom were part of big trades or have already contributed.

The Blue Jays continued to draft and spend well in 2012 and beyond, but spending restrictions limited the ability to bring in so much talent. Nevertheless, this was a critical reversal in strategy and set a strong foundation for what was to come.

2. Winter 2010-11: Perhaps the three best months a GM has had in franchise history

Coming off a surprise 85-win season in 2010 highlighted by several breakouts including most obviously Jose Bautista, as well as several bouncebacks, Anthopoulos could have tried to build off that and push for the playoffs. Instead he saw it mostly for the mirage it was, and sold high to enhance the future while making one bold bet, pivotal moves that paid huge dividends down the road.

First, in December 2010, he moved Shaun Marcum for Brett Lawrie, trading two expensive years of control over a pitcher with injury problems from six years of a quality position prospect. Even though Lawrie settled in closer to league average than the star it looked like he might be, it was still a huge steal. And Lawrie was the centrepiece to acquire Josh Donaldson.

January 2011 brought the shocker of Vernon Wells and his albatross contract being almost entirely dumped. I'm not sure how much credit Anthopoulos really deserves here, since it's clear it was pushed by desperate Angels ownership and he turned around and sold low on Mike Napoli, but nonetheless, it was huge.

That was followed up in February by extending Bautista for four years beyond his last year of control, with an option on a fifth year for $56-million guaranteed, betting on his breakout 2010. It was not a slam dunk that Bautista could repeat his 2010, and indeed he didn't: instead breaking out further in 2011. Had he been a free agent after 2011 instead, he been in for $150-million easily, and maybe $200-million guaranteed.

All in all, you can argue that winter Anthopoulos created upwards of $200-million of value for the franchise. Not bad for three months.

3. Fall 2012: Perhaps the three worst months a GM has had in franchise history

Coming out of 2012, the Blue Jays were at a cross roads. After a second half collapse, they had gone backwards for two straight years while losing manager John Farrell to his "dream job". Jose Bautista and Edwin Encarnacion were a strong core to build around, but aging and most of the prospects were still a couple years away. So they had to decide whether to wait a few years to contend, or make a big push.

And we know what happened. The Marlins deal in November, the R.A. Dickey deal in December, and before that in October moving Yan Gomes who would emerge as a very good catcher. And then they fell completely flat on their face in 2013.

While all those trades ended up looking horrible in terms of value in short order, and losing some excellent prospects was a huge setback, that was only the half of it. In taking on so many contracts, Anthopoulos locked most of it his payroll in for the next three years, which drastically limited his ability to recover from the 2013 catastrophe.

In fact, it became apparent that the 2014 budget was essentially fully spent in late-2012, and there was no money for upgrades in the 2013-14 offseason, save for trying rob Peter to pay Paul by deferring money into the future to sign Ervin Santana. Nor for badly needed in-season upgrades when there some good opportunities available. And when the 2014-15 offseason came, it turned out there wasn't much room either. Anthopoulos probably figured on success bringing higher budgets—but as Warren Buffett famously said, "Only when the tide goes out do you discover who's been swimming naked". The tide went out and the emperor definitely had no clothes.

The moves of these three months were unmitigated strategic failures with lasting consequences, and largely set the stage for 2015. When all is said and done, and value lost will probably total $200- to $300-million. And that's without considering the opportunity cost of having locked up so much salary room for three years.

4. November 2014: Retooling the roster

Last winter, Toronto was coming off a moderately successful 83-win season, in which they occupied first place as late as July. They had emerging young talent, but still a constrained budget and decisions to make on many of the longer tenured players with expiring contracts.

Dustin McGowan, Casey Janssen, Brandon Morrow, Colby Rasmus and Melky Cabrera all left as free agents. Adam Lind would have too via an option buyout, but Milwaukee took him for Macro Estrada on November 1 last year. Though it was not a popular move at the time, it worked out much better than anyone could have imagined and Estrada ended up a stalwart of the 2015 rotation.

A couple weeks later, Anthony Gose was moved for Devon Travis, which ended up filling the biggest hole the Blue Jays had for the preceding seasons. Five days later, Anthopoulos made his first big free agent splash, bringing in Russell Martin on a backloaded deal. Then finally, at the end of the month, he made yet another huge splash, acquiring Josh Donaldson for Lawrie and a prospect haul headed by Franklin Barreto. A good deal then that now looks like a total steal.

The finishing touch was getting Michael Saunders to fill in left field three days into December. Though this one was waylaid by a freak injury, unlike in 2012, all the other moves came up roses in 2015 and look good beyond as well. That said, he failed to upgrade the bullpen which was identified as the biggest issue, and that did have repercussions in 2015.

5. Trade deadline 2015

The other major development in the 2014 offseason was the Blue Jays looking for a replacement for Paul Beeston as President, with franchise owners Rogers Communications' top brass hamhandledly reaching out and targeting baseball people like Kenny Williams and Dan Duquette. This, coupled with a failure to make the playoffs despite the big 2012 push and running top-10 payrolls, clearly put Anthopoulos on notice.

With reports now indicating he was only offered a one-year extension this past summer, the Jays pursuing a baseball guy to install above him, and the Jays once again sitting around .500 well out of the division or wild card position (despite a great run differential indicating they were much better), it would have obvious to Anthopoulos inn late July that barring a drastic turnaround he was in trouble. That gave Anthopoulos every incentive to go for it even if it meant selling the future.

And the rest is history, he moved 11 prospects, the team caught fire and went on a memorable two-and-a-half month run. Which leads us now, and the Blue Jays now wanting to keep him but unable to unwilling to give him the same level of autonomy in baseball matters that he previously had.

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In sum, of these five big strategic turns, four of them worked out well or very well and only one was a disaster. The first two successes went a long way towards digging the franchise out of the hole the previous GM left behind. But there's a cautionary tale here, since that one failure set the club back significantly, and it took another two successful strategic turns to at least partially reverse the damage done and finally get the Blue Jays to the promised land.