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

Ian Hunter
5 years ago
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.

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