Anthopoulos’s Blue Jays remake has proven to be gamble worth taking

Atlanta Braves GM Alex Anthopoulos joins Sportsnet's Starting Lineup to discuss his immediate doubt after signing Jose Bautista's original 5-year deal with the Blue Jays in 2011, and why former Jays slugger didn't work in Atlanta.

TORONTO – Here’s an intriguing question for Toronto Blue Jays fans to ponder with the end of the club’s competitive window nigh and the full brunt of the aftermath nearly here: Knowing all you do now, would you do it again?

Certainly it’s a timely discussion with former general manager Alex Anthopoulos’s new team, the Atlanta Braves, in town for a two-game visit. And unlike his still polarizing departure after the 2015 season and the bevy of unanswerable what-ifs left to linger, there’s no need to delve into the abstract to have that conversation.

Starting with the Nov. 28, 2014 acquisition of Josh Donaldson from Oakland for Brett Lawrie, Kendall Graveman, Sean Nolin and Franklin Barreto – a stunning deal that came 10 days after free-agent catcher Russell Martin signed an $82-million, five-year contract – Anthopoulos cleverly leveraged his farm system to remake the Blue Jays within his payroll parameters and end a 21-season playoff drought.

Over a span of 10 months, Anthopoulos traded 18 minor-leaguers to land Donaldson, Troy Tulowitzki, David Price, Ben Revere, LaTroy Hawkins, Mark Lowe, Cliff Pennington and Darwin Barney, while also adding international spending pool room to ease the penalty on Vladimir Guerrero Jr.’s signing.

Led by Donaldson’s 21.9 WAR per Fangraphs, the players he acquired have provided the Blue Jays with 29.7 WAR. The players traded away have so far provided their clubs with 9.9 WAR, led, surprisingly, by left-hander Matt Boyd’s 3.8.

That tally can certainly change as some of those players continue to develop, but none of them to this point would have altered the Blue Jays’ fortunes in a significant way. While certainly the transactions tore through the farm system’s depth, an issue that’s impacted the big-league club the past two years, the ledger is firmly in the Blue Jays’ favour based on value alone, without calculating what the post-season runs of 2015 and 2016 have meant to the team and the fan base on a much more holistic scale.

"Trading someone from the minor-leagues does not make them a prospect," Anthopoulos said during a late spring interview. "We know with all the players in the minor-leagues, they’re not all prospects and we may trade someone that might be viewed as a prospect by some other team and not view it the same way. Not to speak ill of anybody, but even some of the players we traded in Toronto, respectfully, some have been released, some have retired. I don’t know that, in fairness, all of them were prospects. They may have had some type of industry value at that moment in time, but we all know that can change a month from now, two months from now. They’re like stocks, and the value can do down to zero."

Contrary to the perception created by his penchant for big deals, the Blue Jays integrated several young players during Anthopoulos’s run as GM, highlighted by Aaron Sanchez, Marcus Stroman, Roberto Osuna, Kevin Pillar and Ryan Goins. Ryan Tepera and Danny Barnes have largely emerged since his departure while the prospects he left behind include Guerrero, Anthony Alford, Ryan Borucki, Danny Jansen and Sean Reid-Foley. Depth pieces like Dalton Pompey and Dwight Smith Jr., are also his.

Really, for all his deal-making, the one player he traded away that fans continue to pine over is electric-armed right-hander Noah Syndergaard, who for all his awe-inducing velocity has still only logged 428.2 big-league innings, slightly more than half the 824.1 frames R.A. Dickey threw for the Blue Jays.

On At the Letters, Ben Nicholson-Smith and Arden Zwelling take fans inside the Blue Jays and around MLB with news, analysis and interviews.

Young pitching proved to be a fruitful currency for Anthopoulos, who prioritized arms in the draft because he believed it was hard to recruit free-agent hurlers in the American League East and because he felt they were the best commodity to move in the trade market.

"The other part is position players can get blocked," he explained. "If you have two guys behind the plate, someone is getting moved. You can’t have too many starters, too many relievers. There’s always room. In trades and so on, it was good currency, as well, and we could go get position players."

During that pivotal 10-month span, 14 of the 18 minor-leaguers he traded away were pitchers and some of his other most prominent deals – including the Marlins and Mets blockbusters and J.A. Happ’s initial acquisition in 2012 – were built around young arms.

Some of them, such as Joe Musgrove, Asher Wojciechowski, Anthony Descalfani, Justin Nicolino, Daniel Norris, Kendall Graveman, Jeff Hoffman and Boyd have delivered some big-league value, but hording them and waiting for them to arrive would not have altered the Blue Jays’ direction.

Knowing which chips to use and when to cash in was a hallmark of his run with the Blue Jays.

"I remember my first year, we were trying to get a player who went on to become a really good player who is still playing today and we got asked for Justin Jackson and Brian Jeroloman. Jackson was a shortstop prospect, Jeroloman was behind the plate and there was a reluctance to do it," recalled Anthopoulos. "They were prospects at the time and we missed out on a guy who’s had a long and productive big-league career because we wanted to hold on to those guys.

"Jackson and Jeroloman weren’t going to necessarily keep that value in perpetuity, it just doesn’t work that way. The easiest thing is to keep all of them, but we know it’s not reality. There came a point in time where they didn’t have any currency, they didn’t have any value. That’s part of knowing your own players well. You’re not always going to be right, we make mistakes, but I do think it’s important to try to capitalize sometimes by turning in some type of currency into big-league players. When we draft these guys, we’re hoping to get big-league value. There are a lot of players down there who may not even get a day."

The players Anthopoulos picked up leading into and during that 2015 season certainly got more than a day, and helped give Blue Jays fans the club’s best days since 1992-93.

So, knowing all you do now, even with the looming pain to come, would you do it again?

Yeah, absolutely, without a doubt you would.

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.