4 teams that will sorely regret letting Jordan Montgomery sign elsewhere

At long last, Jordan Montgomery has agreed to terms on a new contract, joining the Arizona Diamondbacks on a one-year deal worth $25 million. He also has a vesting player option for a second season at $25 million if he starts 10 games. Barring injury, he will.

Montgomery is the last of the famed 'Scott Boras Four' to land his next gig, following the same short-term, "flexibility"-infused pathway as Cody Bellinger in Chicago, as well as Blake Snell and Matt Chapman in San Francisco.

After helping the Texas Rangers defeat Arizona in the World Series, Montgomery now flips to the NL champs. The talented southpaw will join a loaded rotation that already features right-handers Zac Gallen and Merrill Kelly. Arizona was an underdog last season, but nobody will make that mistake in 2024. The Diamondbacks are very, very real.

In the end, Montgomery was willing to come off his long-term demands to sign a relatively low-risk contract in Arizona. There are multiple factors at play here — most notably the D-Backs' contending status — but it certainly feels like several teams dropped the ball.

Of all the Boras clients, Montgomery probably inspires the least controversy. He's a rock-solid, durable ace who just pitched a great postseason en route to his first World Series victory. So, the Diamondbacks are winners. Here are the teams who don't get to claim that title.

4. Jordan Montgomery will be sorely missed by the Rangers

Thanks, Captain Obvious.

The Rangers let Jordan Montgomery walk for vague financial reasons tied to a volatile TV contract. Now, the season is set to begin with Max Scherzer, Tyler Mahle, and Jacob deGrom all on the IL. Not the ideal start to Texas' title defense, that much is for sure.

Generally, the reigning World Series champs should be willing to stretch their budget to maintain a competitive status. The Rangers aren't out of the race by any means, but the Montgomery trade was integral to Texas' late-season surge. The Scherzer trade too, but he's on the wrong side of 40 with mounting injury concerns. Montgomery's absence will be deeply felt.

Not only did Montgomery leave, but he leapt across enemy lines to the World Series runners-up. Texas won't face Montgomery often in the regular season, but the threat of a rematch will loom large. Who has a better chance of winning a ring next season, the Rangers or Montgomery? I'll let you answer that, but the choice seems clear from my vantage point.

The NL West is cutthroat, but Montgomery is joining an ascendent team with two established aces already in the rotation. That's oddly reminiscent of the Rangers last season. Montgomery has the stuff to take Arizona to the next level. He didn't sign a long-term contract either, so the risk would have been minimal for Texas.

This is unequivocally a mistake from the Rangers' front office. It's that simple.

3. Well, now the Phillies could face Jordan Montgomery in the playoffs

There were rumblings of the Philadelphia Phillies potentially gunning for Jordan Montgomery, but the front office ultimately bowed out for luxury tax reasons. The Taijuan Walker injury isn't necessarily a reason to panic, but Philadelphia's depth behind the 1-2-3 punch of Zack Wheeler, Aaron Nola, and Ranger Suarez could be put to the test early.

Few teams are more expensive than the Phillies, who have significant long-term money wrapped up in several players (including their two aces). In that sense, not dropping another $25 million plus tax on Montgomery is understandable, even logical. Philadelphia certainly doesn't need him as much as other rumored suitors.

But, in letting Montgomery slip away, the Phillies allowed the competition to gain strength. The Dodgers and Braves are both better this season, at least on paper. The Giants also made serious efforts to stockpile talent. The NL warpath has not gotten any easier, and now Philadelphia's foremost foe — the team that prevented the Phils from reaching back-to-back World Series — just added a game-changing weapon.

Arizona has the best rotation in the National League on paper, in addition to an upstart group of hitters that out-whacked Philadelphia when it counted in October. The Phillies signing Monty would have been a case of the rich getting richer. Well, the same can be said for Arizona, with Philadelphia on the wrong end of that mounting wealth gap.

2. Why haven't the Red Sox done anything?

Okay, maybe that's not fair. The Boston Red Sox extended Brayan Bello, swapped Alex Verdugo for Tyler O'Neill, and added Lucas Giolito to replace the outgoing Chris Sale. Still, after a flurry of moves, it feels like Boston has moved laterally at best. Probably declined.

Craig Breslow was supposed to reinvigorate the front office and put Boston back on the winning track, but right now, it's hard to imagine the Red Sox putting up any sort of fight in the AL East. New York went and got Juan Soto, not to mention Verdugo and Marcus Stroman. The Orioles traded for Corbin Burnes. The Rays didn't do much either, but Tampa won 99 games last season. That's 21 more than Boston.

Now, the Red Sox will be without Giolito for the entire season after he suffered an elbow injury, casting doubt upon their rotation. A lot is riding on the development of 24-year-old Bello, who probably isn't ready to lead a contending bullpen. Boston could have at least pretended to care about winning by adding Montgomery, especially on a short-term deal, but alas. The Red Sox are content with mediocrity for the moment.

There will be more opportunities for Boston to upgrade the pitching staff, but few options will offer more stability than Montgomery. Not to mention his postseason experience, which would surely help a young team trying to make the leap.

1. Who is going to start in Gerrit Cole's place for the Yankees?

The technical answer to that question is Nestor Cortes. But, in reality, the New York Yankees are in a world of worry with Gerrit Cole set to miss the first month or two of the season. New York avoided Blake Snell (and presumably Montgomery as well) due to the severe luxury tax penalties that come with adding $25 million-plus to the books. But, while New York is effectively dodging the tax, the Yankees could be digging their own grave in the crowded NL East.

We cannot overstate how good the Orioles will be next season. The Rays are a tough bunch too, not to mention the 89-win Blue Jays. New York probably doesn't have to worry about Boston, but the rest of the division is a free-for-all — even with Juan Soto in the mix. And, mind you, Soto is under contract for one year. New York is on the clock, with only a limited window to win Soto over.

New York's rotation is dotted with question marks and what-ifs. Nestor Cortes is excellent at his apex. So is Carlos Rodon. But what are the actual odds of either past prime ace reaching said apex? The same can even be said for Marcus Stroman, who comes with his own set of injury concerns.

It would be much easier to say "Cole will be back eventually, don't worry," if the Yankees had another bankable ace on staff to hold them over. Monty will need time to ramp up himself, but in the end, he was New York's best shot at limiting the damage caused by the Cole injury. We are also talking about the Yankees of all teams, so the "luxury tax" excuse falls a bit flat. New York has always paid to win. Why stop now?