The 38-year-old originally joined the Blue Jays in 2003 as a scouting coordinator, but he later received promotions to assistant general manager and then GM. He made a surprise exit at the end of the 2015 season, citing that it was no longer the "right fit" after Mark Shapiro had been named the club's new president.
Anthopoulos was inundated by media requests in the city where he still lives, and as a result, he decided to do a news conference. He touched on a wide variety of topics about his time in Toronto, and here are some of the highlights:
On his reasons behind walking away at the end of 2015...
Anthopoulos: "I know a lot was made that I wasn't as forthcoming, or maybe it should have been a little more specific, but I wanted to keep that more private overall ... I did my best to try to enjoy the playoffs. I really made a conscious effort to try to enjoy it. And until the decision is final, it's not final.
"I would say through the end of the month of August, I expected to be here for five, 10, 20 years, whatever it was going to be, and then things rolled into September, and that's probably the first time it entered my mind that it might not be back. But certainly the decision wasn't done until the end."
On ownership and payroll during his time in Toronto...
Anthopoulos: "I know a lot was made of the ownership here. I can tell you, when I was in the job, no one would probably believe me, but I think people would believe me now, I'm certainly not tied to it. But when it came to ownership, when you made the recommendations from a baseball standpoint, you got the support. So, ownership never told you 'You can't do so many years on a contract, you can't have this type of AAV, you can't structure a contract a certain way.'
"My experiences were always: if it fits within the payroll that you have, you have the ability to do what feel is best for the organization. So anytime that there was some talk about ownership not allowing us to do this, or not allowing us to do that, that never happened. There may have been scenarios where financially we were at our number, and that wasn't going to change ... but you had your number and you worked with it."
On how much offseason planning had been done before he left...
Anthopoulos: "We had gotten to the point where we were ranking free agents, and small things we had just started. Who knows if they would have gotten done? I give Tony LaCava and the group at the time [a lot of credit for doing] an unbelievable job with guys like [J.A.] Happ and [Marco] Estrada. Where we got at that time was we weren't really down in trade talks; we had some things that we were going to follow up from July.
"We had talked about Happ a little bit, just because we had talked about acquiring him in July ... Estrada, I think when we came back from the playoffs, I talked to Marco in the playoffs, told him we wanted him back. I talked to his agent as well a little bit and that we would deal with it when the offseason got going. But we never got into money and years.
"I can't tell you we would have got those deals done. That's the extent of it. The rest we ranked some relievers and things like that. But Tony and the guys worked fast. Obviously a guy like [Jesse] Chavez we talked about, but we never talked to Oakland about Liam Hendriks for Chavez. We were going to go after him again just follow up on July, but that was it."
On looking back about past deals that were made or not made...
Anthopoulos: "As time goes on, I look back and say what if we had gotten Ben Zobrist? That would have been the first deal; Kansas City if they don't have him. That would have been the first deal, I don't know. It may have influenced some other deals, and we may have not had the players to make the other deals.
"So it felt like at one point we had gotten close, but we weren't willing to give up an extra player or two to get it done. But that's probably the one I thought about the most. What if we had done it? You get to Game 7 in Kansas City, who the heck knows what happens? I haven't dwelled on it that much, but that's probably the one I've thought about a little bit."
On the R.A. Dickey trade for prospects Noah Syndergaard and Travis d'Arnaud...
Anthopoulos: "We felt that we were going to make a run in 2013 ... We had lost three-fifths of the rotation in 2012. (Brandon) Morrow really looked like he was starting to emerge as a frontline starter ... [Ricky] Romero, even though he had been an All Star the year prior, the second half of the year he really started to come undone a little bit.
"Then we had (Jose) Bautista and Edwin (Encarnacion), I don't want to say in the prime of their career because I think they're good players and are going to be for a long time, but we had them under contract for a fair bit of time. We felt like we were at a bit of a crossroads in terms of 'Do we scale it back and strip down?' Maybe those guys get moved. Do you trade Edwin? Do you trade Jose? It's hard to be in the middle, and I think for any sports team that's not the appropriate place to be.
"The thought was three years in a row, and beyond, to be able to get the playoffs and win the World Series. The thought was always that it could be what it is today in terms of attendance, TV ratings, fan interest. The belief was there. It was almost like a wick and you needed to light it. And if you could, it would open up a lot of things. That's what I'm most proud of. Seeing where the sport is in Canada right now, seeing how the organization is viewed and the fan interest."