If fans of the Los Angeles Angels are being honest with themselves, there was next to no chance that their team was going to sign Jordan Montgomery. As clear a roster fit as a big name pitcher like Montgomery (or Snell/Yamamoto/etc) was, the Angels have steered clear of all of the big names this offseason and it never made a lot of sense that Arte Moreno would change course and start spending again, especially on an imperfect pitcher.
However, those are arguments for why the Angels weren't going to give Montgomery and Boras the deal that they were looking for, which was rumored to be seven years at over $25 million a year. When Montgomery ultimately decided that he was going to sign with the Diamondbacks on a glorified one-year deal, it does beg the question as to why the Angels didn't jump at that opportunity.
The Angels only have their own bad decisions to blame for not landing Jordan Montgomery
It's important to remember that there are two sides to every free agent decision when thinking about Montgomery. It is entirely possible that the Angels decided it was either too late in the game to go out and sign Montgomery even on a short-term deal, or that the front office and ownership were going to hold firm on limiting their payroll in 2024. As good as Montgomery is, it would have been pretty disruptive to add him into the mix right before the season started.
However, a more likely scenario is that Montgomery just wanted to play for a better team if he was going to take a short-term deal -- something that was reported earlier this offseason. Monty is clearly looking to reset his market and try his hand at free agency again very soon (probably after the 2024 season if we are being honest) and playing for a contender this year is his best option for that path. Teams like the Angels and Red Sox could have certainly used him, but they are more "interesting" than actual 2024 contenders right now.
It's that scenario that shows how the last few years have gone even worse for the Angels. If the Angels had been able to keep Shohei Ohtani and actually build around him as well as Mike Trout, then maybe a guy like Montgomery would have been inclined to sign with the Angels. Instead, LA fumbled the bag and look like an organization that is lost at the moment.
It's no wonder Monty signed somewhere else even if the Angels were willing to pay him.