Yankees never got close to a Jordan Montgomery deal despite interest

HOUSTON — Word is Yankees owner Hal Steinbrenner badly wanted to bring back free agent Jordan Montgomery, the last remaining available pitcher, to bolster their capable but questionable rotation heading into their opener Thursday against the Astros. And Yankees general manager Brian Cashman and Montgomery’s agent, Scott Boras, had each other on speed dial over the last several days.

Ideas were exchanged. Arguments were made. Points were considered.

But the sides never got traction, or even close to traction.

The issue, as it was with Blake Snell, who went to the Giants, was the fourth-tier, so-called “Steve Cohen tax.” Blame Steinbrenner if you will, but that 110 percent tax on teams over the $297M threshold is quite the disincentive for almost all, ironically for probably everyone but Cohen himself (who brought in DH extraordinaire J.D. Martinez late, and will pay that onerous tax.)

While the Yankees had at least one four-year idea for Montgomery, there’s no evidence any official offers were presented (details below on what the Yankees were thinking, if not offering). So Montgomery on Tuesday night agreed to a $25 million, one-year deal with the Diamondbacks that with at least 10 starts in 2024 will become two years at $45M-$50M and include an opt-out.

With the Yankees’ usual lofty hopes but roster diminished by injury — ace Gerrit Cole and veteran third baseman DJ LeMahieu are the headliners on their injured list this time — the Yankees arrived at their personal house of horrors. They’ll start with a makeshift rotation in a year they’re allegedly “hellbent” on winning the championship. These hated Houston Astros (and a few others) have prevented the Yankees from even getting close to their 28th World Series title for going on a decade and a half now.

Jordan Montgomery #52 of the Texas Rangers walks into the dugout from the clubhouse prior to Game 2 of the 2023 World Series

The Yankees were in contact with Jordan Montgomery’s camp, but nothing ever really got going.MLB Photos via Getty Images
Here’s the best news: Cole is said to be “feeling great” and the occasionally whispered target date of June 1 for the best pitcher in baseball seems more realistic than ever. In the meantime, Yankees people hope to remain close to contention until their Cy Young savior returns.

Nestor Cortes, who missed much of last year with hamstring and shoulder troubles, takes the ball Opening Day against Astros star Framber Valdez. Cortes was technically the third choice since Game 3 starter Marcus Stroman turned it down to stay on his schedule.

Yankees GM Brian Cashman speaking to the media during Spring Training Media Day

Brian Cashman’s side was hamstrung by the Yankees’ salary situation.Charles Wenzelberg / New York Post
Carlos Rodon follows Cortes in Game 2, and Rodon was so off his game last year he felt the need to add not one but two pitches, which is unusual for a $162M pitcher. It’s still up for debate whether Rodon’s undoing was his health, his stuff or New York, and the popular guess is “a little bit of everything.”

Stroman, who’s thrilled to be a Yankee (and not a Met), improving young right-hander Clarke Schmidt and Luis Gil, who won the open fifth spot, round out the rotation, for now.

Montgomery would have helped, of course. And the Yankees know it.

Yankees analytics people (and apparently other analytics people around the league) carried the very same issue with Montgomery that led them to trade him for defensive outfielder Harrison Bader a year and a half ago. That is that he doesn’t “miss enough bats.” Which seems like a lame complaint for the guy who destroyed these Yankee-killing Astros in the ALCS only last October.

The Yankees also wondered if Montgomery really wanted to return. They’d heard that the Rangers were his first choice. And they also heard he might prefer to go south. But of course, they couldn’t be sure.

 Yankees starting pitcher Gerrit Cole #45, walking out of the bullpen at Steinbrenner Field
Gerrit Cole’s June 1 return date feels realistic.Charles Wenzelberg / New York Post
Anyway, the Yankees still made the calls. They formulated an idea that might have worked if Montgomery eagerly wanted to be back, desperately sought the security of a multiyear guarantee or had absolutely nothing else.

In the end, though, their idea didn’t match the active D-Backs, who are well under any tax threshold, and could offer an average annual value that is more becoming a No. 2 type starter. Montgomery’s camp suggested shorter deals with higher AAVs to the Yankees, too, but for them, the tax meant even a $20M salary would cost $42M — which is $6M more than Cole makes.

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The Yankees’ suggestion was something else entirely.

Their idea was for $72M over four years with $40M of that — $10M per year deferred for 10-17 years — that’s $5M payments in 2034-41. According to my deferral expert, the Yankees’ idea would have been worth about $46M in net present value — or $11.5M per year for Montgomery (and cost the Yankees $24.15M per).

With $10M a year deferred, Montgomery would take three years to pocket $24M when he’s getting $25M for one in Arizona.

And he would take until 2041 — when he’s 48 — to match what he’s getting in Arizona in two years, assuming he vests the second year with 23 starts and earns the full $50M.

The Yankees put serious work into it. They made many calls, and they got very creative to make it work from their perspective. But in the end, they probably came closer to winning the 2023 World Series than they did to signing Montgomery.

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