Who won the Zack Wheeler for Jordan Montgomery trade between the Yankees and Mets?

A lesson in reserving judgment

8/4/2022, 11:21 PM

In the final days of July 2019, Yankees general manager Brian Cashman and Mets GM Brodie Van Wagenen talked and texted frequently, tossing concepts back and forth, exchanging names to see if they could match up on a trade.

The Mets scouted pitching prospect Deivi Garcia and liked Aaron Hicks. The Yankees expressed a willingness to take on Jeurys Familia’s contract, and inquired about Noah Syndergaard.

Finally, the sides agreed to move Zack Wheeler to the Yankees and Jordan Montgomery to the Mets, according to high-ranking sources from both teams (we have previously reported that the clubs agreed to a Wheeler trade, but the Montgomery return is new information).

Van Wagenen received approval from then-owners Fred and Jeff Wilpon, who were ready to trade with the Yankees, despite a widespread belief that they would not do so. Done deal, pending medicals.

Then, at the last moment, the Mets’ medical team decided it was uncomfortable with Montgomery, who was recovering from Tommy John surgery. As with the infamous Wheeler and Wilmer Flores for Carlos Gomez trade in 2015, medicals killed a deal after the GMs agreed to it.

Why get into all this ancient history? Well, it’s kind of interesting for trade nerds like me, and probably you, to know that the Yankees and Mets actually agreed to a deadline quasi-blockbuster. But mainly it’s an instructive example of how difficult it is to evaluate a GM and his or her trade deadline, even years after the fact.

The same logic applies, perhaps even more so, to Van Wagenen’s 2018 trade of Jarred Kelenic for Robinson Cano and Edwin Diaz. For years, Mets fans dismissed that deal as a major blunder. Now, given what Diaz and Kelenic have contributed to their teams for going on half a decade since, it’s clearly one of the Mets’ best trades in years.

The Wheeler/Montgomery deal is another interesting case study. Let’s say the teams had finalized it.

Montgomery was rehabbing from Tommy John surgery, and the loss of Wheeler, both in terms of production and clubhouse morale, would likely have prevented the Mets from enjoying an exciting run in the second half of 2019.

Bad deal for the Mets then. Right?

Well, Montgomery would have come in awfully handy in 2020, when Syndergaard and Marcus Stroman went down, and free agent acquisitions Michael Wacha and Rick Porcello underperformed. He would have been useful last year, too, when Carlos Carrasco began the year with an extended stint on the injured list, and Jacob deGrom ended it that way.

So … good deal for the Mets?

Bad?

Depends?

As for the Yankees, they would have had Wheeler in their 2019 playoff rotation against the Houston Astros, against whom Chad Green started in the Game 6 of the American League Championship Series. That was the Jose Altuve “buzzer” game. We can’t say that the Yanks would have won with Wheeler, but they would have had a better rotation.

The Mets were wrong about Montgomery’s medicals. After that day, Montgomery pitched 316 innings in the regular season and four in the postseason. In each of the past two seasons he has posted an ERA under 4.00. Unspectacular competence like that carries major value for a team, both competitively and financially.

This week, Montgomery netted the Yankees Harrison Bader, the talented outfielder under team control through next season, in a trade with the St. Louis Cardinals. What if Bader helps the Yankees win a championship? Would we then say that the Yankees dodged a bullet by not getting Wheeler in 2019? Does your head hurt now?

In conclusion, who won the Wheeler/Montgomery trade (had it been finalized)?

The Yankees did (had they won the 2019 World Series). The Mets did, (had Montgomery pitched well for them in 2020, ‘21 and ‘22).

While we’re at it, who won the Mets/Mariners trade?

It was the Mariners, in a blowout, when Diaz blew the season in 2019 and Cano kept taking PEDs. Now it’s the Mets, because Diaz is the best closer in the game, Cano cost only money, and both Kelenic and pitcher Justin Dunn have failed for years to develop into useful big leaguers.

Will it be the Mariners in 2041, when Kelenic arrives at his Hall of Fame induction ceremony? Or the Mets this October, when Diaz strikes out Aaron Judge to win the World Series?

See how hard it is to evaluate these GMs and their deals?

Maybe we should stop trying to declare deadline winners and losers of these things, and just embrace the complexity.

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