Diamondbacks to sign World Series-winning pitcher on $25M deal

The Diamondbacks and left-hander Jordan Montgomery are reportedly in agreement on a one-year deal that guarantees him $25M. The deal includes a $20M vesting player option for the 2025 season, with Montgomery earning the ability to opt out if he starts at least ten games in 2024. Montgomery’s option will vest at $20M if he makes ten starts, with an additional $2.5M added to the option upon reaching 18 starts and 23 starts during the 2024 season. The deal is pending a physical.

The deal brings to a close a lengthy free agency for Montgomery, who defeated the Diamondbacks in the 2023 World Series alongside the Rangers just five months ago. Arizona will be the 31-year-old’s fourth team in the past three seasons. After spending his entire career in a Yankees uniform to that point, the southpaw was swapped to St. Louis in exchange for center fielder Harrison Bader at the 2022 trade deadline. 

Montgomery found great success in St. Louis, delivering a 3.31 ERA and 3.50 FIP in 32 starts for the club before he was once again swapped in a deadline deal, this time to Texas as the Cardinals faced their first 90-loss campaign of the 21st century. His strong performance continued in Texas as he pitched to a sterling 2.79 ERA down the stretch before delivering a 2.90 ERA in 31 postseason innings as the Rangers claimed their first World Series championship in franchise history.

While Montgomery has emerged as a starter capable of comfortably pitching at the front of a playoff rotation in his 50 appearances (both postseason and regular season) since leaving New York, he showed himself to be a quality mid-rotation arm even during his days in the Bronx. While he missed much of the 2018 and 2019 campaigns while rehabbing from Tommy John surgery, the southpaw pitched to a respectable 3.94 ERA and 3.90 FIP in 98 appearances across five-and-a-half years with the club. 

During his time in New York, he struck out 22.7 percent of batters faced while walking just 6.9 percent and generating grounders at an excellent 43.7 percent clip. Those peripheral numbers are fairly consistent with the ones he’s posted during his breakout over the past two seasons; since the start of the 2022 campaign, Montgomery has struck out opponents at a 21.6 percent clip while walking 5.6 percent with a 45.3 percent groundball rate.

For the Diamondbacks, the addition of Montgomery further strengthens a starting rotation that the club already took a major step toward addressing when they signed left-hander Eduardo Rodriguez to a four-year, $80M deal back in December. When at full strength, the club’s rotation now figures to feature NL Cy Young award finalist Zac Gallen and Montgomery at the front, with Rodriguez and veteran righty Merrill Kelly in the middle, and youngster Brandon Pfaadt bringing up the rear. 

It’s a massive upgrade from the club’s 2023 group, which pitched to a combined 4.67 ERA last season. That was a bottom-ten figure in the majors last year and placed the club dead last among all 2023 playoff teams. By signing Montgomery, the Diamondbacks have successfully converted one of their biggest weaknesses in 2023 into a clear strength ahead of the 2024 season, at least on paper.

Of course, it remains to be seen whether that on-paper strength in the rotation will yield results. Availability remains a major question mark for the starting staff in Arizona entering the regular season, as neither major pitching addition will open the season in the club’s rotation. Rodriguez was shut down last week due to a lat strain and has no announced timetable for return, and John Gambadoro of 98.7FM Phoenix reports that the club doesn’t expect Montgomery to be ready for at least “a few weeks.” Previous reported had indicated that Montgomery had built up to 75 pitches in his offseason workouts, though said training is no replacement for facing live hitting in organized ball.

Nick Piecoro of The Arizona Republic reports that the delayed start to the southpaw’s season comes with what could prove to be a significant financial benefit. Because Montgomery, who has agreed to start the 2024 season in the minor leagues in order to ramp up for the season, won’t start the season as a part of Arizona’s Opening Day roster, Piecoro indicates that the left-hander will be rendered ineligible to receive a qualifying offer from the Diamondbacks should he return to free agency this winter. 

That removes perhaps the most significant drawback Montgomery faced in signing a short-term deal this winter, as his midseason trade from St. Louis to Texas allowed him to enter free agency unencumbered by draft pick compensation. Had he been eligible for the QO this winter, he’d run the risks of facing a deflated market as a qualified free agent. That possibility is now no longer a concern.

The addition of Montgomery sends Arizona’s already franchise-record payroll to new levels after an offseason spending spree. In addition to Montgomery and Rodriguez, the club also fortified their outfield mix with Joc Pederson, Randal Grichuk, and Lourdes Gurriel Jr. in free agency while swinging a deal to land third baseman Eugenio Suarez to bolster their infield. 

Those additions wound up bringing the club’s estimated payroll (per RosterResource) to more than $167M, with a $215M figure for luxury tax purposes. Both of those figures blow Arizona’s past records of $132M in 2018 and $155M in 2023 (per Cot’s Baseball Contracts) out of the water as the club enters 2024 eager to return to the postseason and establish themselves as a top contender in the NL alongside clubs such as the Dodgers, Braves, and Phillies.