Retracing Diamondbacks' unlikely path to land Jordan Montgomery

Jordan Montgomery’s walk year really could not have gone any better.

The 31-year-old lefty threw 188.2 innings in 2023 and had a 3.20 ERA, both career bests. He made his first 21 starts of the season with the St. Louis Cardinals, where he posted a 3.42 ERA before being traded to the Texas Rangers at the deadline.

Under the pressure of a contentious postseason race, Montgomery thrived. In 11 starts down the stretch, he had a 2.79 ERA, helping the Rangers navigate multiple starting rotation injuries and secure the second AL wild card spot.

In the postseason, Montgomery’s excellence continued. Over 31 innings, he posted a 2.90 ERA, including a 1.29 ERA in 14 innings in the ALCS against a high-powered Houston Astros offense. Without him, the Rangers likely would not have reached the World Series — or, perhaps, even the playoffs.

On paper, Montgomery’s consistency, durability and postseason track record were unmatched in this past winter’s free agent class. Baseball analysts widely expected him to sign a long-term, nine-figure contract.

But on Friday, the Diamondbacks finalized a one-year deal with Montgomery worth a reported $25 million with a vesting player option for 2025.

It’s official.

Jordan Montgomery…you are an Arizona Diamondback. pic.twitter.com/gQ0vgGy3gO

— PHNX Diamondbacks (@PHNX_Dbacks) March 29, 2024

With Zac Gallen and Merrill Kelly already forming one of the best 1-2 punches in baseball last year and fellow offseason signee Eduardo Rodriguez expected back from a lat injury in the not-too-distant future, the Diamondbacks have the makings of one of the best starting rotations in baseball.

The fact that a pitcher of Montgomery’s caliber signed such a low-risk contract was a surprise. Also surprising, of course, was the fact that the Diamondbacks — a team that has long sat in the bottom 10 or so in the league in spending — were the ones willing to pony up and pay what is still a hefty salary for a single season.

So, how did we get here? Here is a look at how the stars aligned.

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How Montgomery signing went down

When asked how the deal came together, Diamondbacks managing general partner Ken Kendrick said “quickly.”

The Diamondbacks had interest in Montgomery from the start of the offseason prior to the team’s signing of Rodriguez, Kendrick said, but the asking price was “way different” from the contract that was ultimately agreed upon.

Ken Kendrick said that Jordan Montgomery was among the starters the Diamondbacks considered early in the offseason.

“We were looking at what appeared to be numbers way different from where we ended up.” pic.twitter.com/ZugH8KL6kA

— PHNX Diamondbacks (@PHNX_Dbacks) March 29, 2024

Over the course of spring training, Diamondbacks general manager Mike Hazen holds frequent meetings with Kendrick and team president Derrick Hall. With Montgomery still on the market toward the end of spring training, Hazen and his staff presented the idea of making a run at him.

Kendrick and Hall agreed to the proposition.

“Ken has consistently said, as we are in the throes of trying to win and compete for a championship, that his support is going to be there for us to be able to pursue things, maybe things that we haven’t done in the past — in the recent past,” Hazen said. “I think the fans are fortunate that we were able to do something like this, I think our team is very fortunate that we were able to do this. We certainly as a front office were fortunate to be able to pursue this.”

The Diamondbacks first made contact with Montgomery’s camp just a few days before the signing was announced.

Of course, all indications are that the deal would not have been possible had Montgomery’s market not stalled the way it did.

“You watch the market evolve,” Kendrick said, “and it moved more slowly than maybe I think any of us would have expected with the top-of-the-line free agents, of which [Montgomery] clearly was one.

“We’re down to near the end of spring, obviously, and he’s still available. We thought it was worth making an effort to approach them. And we did, and it worked out for both of us.”

Kendrick said that the decision to sign Montgomery was not connected to Rodriguez’s lat injury, given that Rodriguez is expected back soon anyway.

Montgomery’s contract pushes the Diamondbacks’ Opening Day payroll into the $170 million range, more than $30 million higher than it has ever been in the franchise’s 26-year history. According to Cot’s Contracts, last year’s Opening Day payroll was around $116 million.

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Scott Boras’ plight

Montgomery, of course, is represented by esteemed MLB super-agent Scott Boras.

Boras said he received plenty of interest in Montgomery from the outset of free agency, but ownership groups were unwilling to commit to long-term deals like they have in the past.

“There were numerous teams,” Boras said, “that wanted Jordan. Baseball ops wanted him. And we have all these calls to say, ‘Just wait, just wait. I think my owner will revisit this.'”

Boras attributed teams’ lack of willingness to commit to long-term contracts primarily to the unknown of future TV contracts, even though, in his estimation, “everybody agrees that they’re going to be much better.”

According to multiple reports, Boras’ initial ask for Montgomery was in the neighborhood of the seven-year, $172 million deal that right-hander Aaron Nola signed with the Philadelphia Phillies in November.

On paper, Nola is a reasonable comp. While he has a leg up on Montgomery in terms of innings — Nola has averaged 193 over the past three seasons compared to Montgomery’s 175 — Montgomery has a 121 ERA+ in that span compared to Nola’s 102 ERA+.

Boras said that Montgomery “probably” could have signed a long-term term deal with a less competitive team, but that he was insistent on playing for a contender.

“Jordan’s edict to me,” Boras said, “was, ‘I want to play for a competitive team. I want to make sure that I’m there. If I have to take something short-term in the end to play for a competitive team, I will.’ And, certainly, that’s how we kind of opened this door.”

Of course, Montgomery is not the only Boras client who signed a relatively short-term deal and received less guaranteed money than expected this offseason.

Reigning NL Cy Young winner Blake Snell signed a two-year million deal worth a reported $62 million with the San Francisco Giants two weeks ago. Third baseman Matt Chapman reportedly got $54 million guaranteed, also with the Giants, over three seasons. Center fielder Cody Bellinger, who is the youngest of the bunch at 28 years old, re-signed with the Chicago Cubs on a three-year contract reportedly worth $80 million. All three of those players have opt-outs that will allow them to re-enter the market next winter.

While Boras was unable to net $170 million for Montgomery, he did manage to protect his client from the possibility of being subject to draft pick compensation next offseason.

At Boras’ request, the Diamondbacks agreed to wait until the day after Opening Day to finalize the deal, making Montgomery ineligible to receive a qualifying offer that could have netted Arizona an additional 2025 draft pick had Montgomery rejected it and signed elsewhere.

Since Montgomery was traded midseason last year, he was also ineligible to receive a qualifying offer from the Rangers. The Diamondbacks, therefore, did not have to forfeit a draft pick to acquire him.

Said Boras: “You shouldn’t be able to, in fairness, be able to acquire a draft pick when you’re not giving one up.”

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Two Words: ‘World Series’

Had the Diamondbacks lost even one more regular season game last year, they would have missed the playoffs entirely. Not only did they make it in, but they went all the way to the World Series — and it is hard to overstate the ripple effects of that unexpected run.

In addition to solidifying their status as a contender, which was a big factor in Montgomery’s desire to play for them, the Diamondbacks’ World Series appearance also brought in significant unanticipated revenue. Without it, it appears that the Montgomery signing would not have happened.

“Thank goodness for last year’s playoff run,” Kendrick said, “because the economics of our ability to justify an investment like Jordan takes was helped by that.”

Kendrick also pointed to strong ticket sales so far this year as a factor in signing Montgomery, which, of course, are also a function of last season’s success. Hall told reporters last week that the team projects an attendance figure north of 2.5 million fans in 2024. The Diamondbacks last eclipsed the 2.5 million mark in 2008.

The team’s decision to spend big on the heels of a playoff run runs in contrast to their approach following their previous postseason appearance in 2017. After winning 93 games and advancing to the NLDS that year, the Diamondbacks made little in the way of impactful offseason additions and wound up missing the playoffs the following year.

The team’s biggest loss that winter was then-outfielder JD Martinez, who put up monstrous numbers with the Diamondbacks after being acquired from the Detroit Tigers at the trade deadline. Martinez reportedly had interest in returning to Arizona, but wound up signing with the Boston Red Sox instead.

Boras, who also represents Martinez, was asked why the Diamondbacks took a different approach this time.

“I just don’t think you want to miss something that has taken a long time to put together,” Boras said. “The sacrifice this organization’s made to get where they’re at, to be at the competitive level that they’re at, to have offense, defense, to have the completeness they have.

“I’m really happy for Jordan and his teammates and the organization because it really illustrates the billboard of competitiveness that I think every fan base would want.”

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Top photo: Kevin Jairaj/USA TODAY Sports