Alex Anthopoulos Spills the Beans on a Bunch of Would-Be Blue Jays Trades

After six years on the job at 1 Blue Jays Way as the “Silent Assassin,” Alex Anthopoulos is finally letting it all out. All those years of soundbites when he said a whole lot, but without very much substance, he’s disclosing a bunch of state secrets from his former days as Blue Jays General Manager.

I, for one, am thoroughly enjoying this new “open book Anthopoulos”. Earlier this year, he said the Jays had a deal on the table for Ben Zobrist at the 2015 non-waiver trade deadline. It turns out that was merely the tip of the iceberg in terms of the kinds of deals AA tried to make happen during his final few years at the helm in Toronto.

Last week, Anthopoulos had a very interesting sit-down on The Lede Podcast with Jeff Blair and Stephen Brunt. It’s a fascinating listen and Anthopoulos opens up quite a bit about his time in Toronto, the inner workings of some of his most famous trades, but more importantly … a bunch of trades that could have happened.

In the span of about 10 minutes, totally unprompted by Blair and Brunt, Anthopoulos reveals a bunch of trades that could’ve taken place under his watch as Blue Jays GM. For one reason or another, these transactions didn’t materialize, but it’s fun to imagine what may have happened if they did.

We did talk about some deals, we talked about getting Chase Headley at the time. Guys like Kevin Pillar were going to have to go back. Sean Nolin was going to have to go back on that deal if they were going to eat all that salary on Headley.

This one sounds like it transpired during the 2013 offseason heading into the 2014 season. To help shore up third base, the Jays wanted to move Pillar and Nolin to get Headley from the Padres, but due to the Jays’ payroll restrictions, if the Jays wanted to the Padres to pick up most of his salary, the Jays needed to give up more in prospect capital.

It’s apparent that AA felt Pillar and Nolin were too steep of a price to pay for Headley, although in retrospect, that’s probably a pretty decent deal for the Blue Jays.

Conversely, if Anthopoulos makes that trade with the Padres, then Nolin isn’t available as part of the potential package which landed Josh Donaldson the following year. It’s crazy to think about the domino effect these potential trades may have had on the future of the Blue Jays.

Brandon McCarthy was out there. McCarthy was going to be available if we were going to offset the money.

I vaguely recall some McCarthy-Jays rumours from back in the day, but oddly enough, the Yankees ultimately got both McCarthy and Headley in two separate trades leading up to the 2014 trade deadline. Yangervis Solarte was part of the package that went over to the Padres in exchange for Headley.

We tried to add J.A. Happ to the Mark Lowe deal and we were out of money. We couldn’t take on the remaining salary because we needed it for the Price deal.

Wait, the Jays could’ve had Happ at the 2015 deadline? Going after Happ would’ve precluded them from getting David Price, but it’s interesting how Anthopoulos wanted to bring back Happ to help solidify the starting rotation. If the club had a little more payroll wiggle room, it sounds like Anthopoulos could’ve potentially added two starting pitchers in late July of 2015.

We could’ve traded for Greg Holland … guys like Osuna, Travis.

I do recall this reporting from late 2014 when Bob Elliott said the “Jays are pursuing the closer”. Anthopoulos didn’t make it abundantly clear, but he certainly gave the impression like Roberto Osuna and/or Devon Travis were the ask from the Royals in exchange for Holland.

We could’ve got Mike Leake, we were out of money.

Thank you, Alex … for not doing that deal.

We talked to Oakland about Scott Kazmir, Daniel Norris had to be in that deal.

In retrospect, all these potential trades provide a great deal of insight into the volume of trade proposals that are out there between front offices. Very few deals actually make it to the finish line, which means dozens and dozens of trade proposals like the ones above simply wither on the vine.

According to this piece by Steve Simmons from the Toronto Sun, Anthopoulos pestered Billy Beane for weeks about the availability of Josh Donaldson. I like to envision AA hounding other General Managers like George Costanza trying to sell computers. “You want to trade Josh Donaldson? NO? WHY NOT!!?”

Seriously, listen to that whole Lede podcast episode from start to finish. If not to hear about these failed Blue Jays trades, tune in to hear Anthopoulos discuss the inner-workings of the Troy Tulowitzki deal. It’s a riveting glimpse into all the factors that play into a blockbuster trade.

  • sons

    For years I have been saying that AA was screwed by payroll restrictions. He wanted to deliver a winner so badly and he was always pushing for more. Now obviously Rogers has raised payroll, but we’re still not really that high up there. And when you look past this year we drop way down and then way way down near the bottom for 2020.

    • GrumblePup

      I’m confused. It sounds like you’re complaining that money is coming off the books over the next couple years.

      You know the Jays are gonna have to sign new players to replace the ones that are leaving right? So all that money coming off the books will be available to spend on other people.

      Just because they only have like $55 million on the books for next year doesn’t mean thy can only spend $55 million next year.

      • Paul Beestons Grass Surface

        It also doesn’t mean that current payroll will be available to spend. It’s Rogers we are dealing with. They don’t care about the product nor the fan. Just the bottom line.

        • Nice Guy Eddie

          Right,. Because spending $23.5 million for JD, pissing $20 million a year down the toilet on Tulo, and paying $20 million for a backup catcher is making us a lot better.

          • drunk man walking

            maybe that is why they wanted Shapiro, since in his tenure in Cleveland he always managed to make money for Dolans despite the fact that his teams were mostly terrible and no one bothered to go to the stadium.

        • GrumblePup

          Oh yeah. You’re right! The Jays will never spend money on a player again! How could I have been so stupid!?

          I bet the team jsut up and moves to Cleveland because that’s so obviously where Shatkins wants to be! If Rogers had their way, the Blue Jays would turn into a new form of internet that only they could provide and thus make more money!

          • Paul Beestons Grass Surface

            No one is saying that. We just have to take a look at the history of Rogers. There is no guarantee that they will maintain a payroll in the top 10. Again it’s about money. If they can make the same kind of money, on a middling payroll, they will do it. They are a corp, without the passion of a fan. We all wish they would run it they way we want, but it’s about money. However, I’m hoping, that they got a taste of the way things can be, in 2015 and 2016. And will provide payroll, as the jays grow beyond 2019. Time will tell. But I think, with the low payroll, and cheap young players, Rogers may be hesitant to ante up again, especially if the Jays are winning. I know, it seems to go against what the team should do. But it’s all about the bottom line. If the team is doing well, and the money is rolling in, why would Rogers provide more to bring on a veteran. It will be up to Shapiro and Atkins to make their case, but I wonder if we will end up back in the babble talk years, where Rogers would do anything if Beeston and/or AA asked them. Funny how they never asked…until 2015…not sure if they did, assuming they did to take on payroll like that.

          • GrumblePup

            That’s all well and good, but it’s also completely asinine to complain about what the payroll is in 2020 (dude said “then way way down near the bottom for 2020”) Like, of course it is. Only one player has a guaranteed contract right now for that season.

            In 2021, the jays only have $4 million on the books! How can we possibly field a team with only $4 million!?!?!

            That’s not how contracts work.

            Yes, there will (hopefully) be a bunch of our young guys up in the big leagues by then, so the payroll will be smaller. That is not a bad thing and it is not indicative of “cheap Rogers never gives us money!”

            I am well aware that in the past, Rogers hasn’t always come up with the money when we want it. But being able to keep payroll low by paying Bichette, Vlad, SRF etc (or whoever else comes up) IS NOT A PROBLEM.

            The benefit of have a team of good young players is that they don’t cost much. If anything, this should make it more likely that Rogers would spend money on a veteran free agent.

            As a company that is “without the passion of a fan”, when do you think it makes the most sense to bring in a veteran player that would genuinely make a difference to the team?

            When the Payroll is already $155 million? Or when the team is competitive, full of young cheap controllable talent and the payroll is only $85 million (I’m using a number that would put the Jays ‘way down near the bottom’ for this year)?

            My point is, don’t complain about a budget in 2-3 years when there is absolutely no indication of what that budget is going to be.

          • Paul Beestons Grass Surface

            Hey GrumblePup. Asinine? What are you bitching about. What was my whole point, and where was I “Complaining” about payroll. I pointed out that nothing is guaranteed with Rogers. Ahh, the hell with it.

          • GrumblePup

            Paul, I was calling sons complaint that the Jays payroll for 2020 is down near the bottom of the league asinine.

            There is 1 player on the books for 2020. Of course right now it’s at the bottom of the league. But the Jays have to sign more players. Complaining about the payroll 2 years from now is actually insane in this situation.

          • Paul Beestons Grass Surface

            Umm…..can you picture Homer meekly saying “doh…” That me’s me over in the corner, sorry man. I miss disquis, really easy to see where comments were coming from. For the record, I agree with what you say, but I still stand by my Rogers comments. It’s unfortunate, but we have to deal with the big Red elephant in the room, that they are. Onwards and upwards!!!