The Cardinals' best move of the offseason may have happened before it even began

The Cardinals' best move of the offseason may have happened at the Trade Deadline.
Milwaukee Brewers v St. Louis Cardinals
Milwaukee Brewers v St. Louis Cardinals / Dilip Vishwanat/GettyImages

Back in July, the St. Louis Cardinals found themselves in an unfamiliar position as sellers.

No one enjoyed what happened in 2023 from the Cardinals' perspective, and anyone following the team would have liked things to have gone differently, but the place they found themselves in carved the way for them to make perhaps the best move of the offseason...on July 30th.

For a team like the Cardinals, who are seemingly always in contention, the offseason begins after their postseason elimination. But when you find yourself in the seat of a team that is selling, the offseason begins at the Trade Deadline.

If you go back to that time, there were many fans against the idea of trading Jordan Montgomery. Why would the club deal away a really good starting pitcher when they need pitching badly? But the Cardinals had the foresight to see that he would bring them back a ton of value in return, and the might have struck gold with the deal the Rangers offered them.

Before we get into the package the Cardinals got in return, I always want to acknowledge that the Cardinals likely would be sitting in the exact same spot with Montgomery today if they did not deal him. His market has exploded, and although some of that has to do with his postseason performance, he was already pitching really well for St. Louis during his last two months with the club, and even without the postseason run, his contract would have inflated a ton like it has now. The Cardinals would have gotten a draft pick in return for him, assuming they did not sign him.

Instead, the Cardinals dealt Montgomery and Chris Stratton for Thomas Saggese, Tekoah Roby, and John King, a deal that might make the biggest impact on the future of the Cardinals out of any deal made this calendar year.

John King, the one with the lowest ceiling of the bunch, already posted a 1.45 ERA in 20 games for the Cardinals out of the bullpen, giving them another arm for their bullpen mix going forward. I'm not very high on King, but he did produce in 2023, and at the very least, he's a serviceable arm going forward.

Tekoah Roby now joins Tink Hence as the top two pitching prospects in the Cardinals system, and depending on who you ask, some are higher on Roby than they are on Hence. One of those outlets is Baseball America, which has Roby ranked as the Cardinals' number two prospect behind Masyn Winn because of his mid-90s fastball paired with a plus curveball and plus control (subscription required). Many project Roby to be a middle-of-the-rotation starter, and if he continues to take steps forward, he could project a bit higher. The Cardinals haven't had an internal option emerge as a number three starter in years.

On top of that, the Cardinals got Thomas Saggese in the deal, who at the moment, looks like another versatile infielder with an above-average to-plus bat at the plate. Saggese had an incredible 2023 season split between the Rangers and the Cardinals, and after winning the Texas League Most Valuable Player Award, will get an opportunity in Spring Training to showcase his progress against big league pitching.

Even if the trio doesn't have a direct impact on the Cardinals in 2024 due to their play (although, King and possibly Saggese may factor into things), the deal looks like one that can indirectly help the Cardinals both this upcoming season and for years to come.

The addition of Roby to this system is a massive boost to the Cardinals' pitching depth long-term. They can now look at Roby, Hence, Cooper Hjerpe, Gordon Graceffo, Max Rajcic, Ian Bedell, Sem Robberse, Michael McGreevy, Zack Showalter, and Adam Kloffenstein all as potential rotation options for the future. The Cardinals also now have more firepower to use in trades, as Roby, Robberse, Kloffenstein, and Showalter were all added at the deadline.

Saggese, like Roby, either gives the Cardinals a valuable bat to add to their lineup soon or someone they can use to acquire more pitching in the near future. Had the Cardinals held onto Montgomery at the deadline, they'd be a lot thinner in terms of valuable trade assets, and the possibility of a major trade would be a lot lower.

The Cardinals replaced Montgomery's production from last year and then some with the addition of American League Cy Young runner-up Sonny Gray. Gray provides veteran leadership and a firey edge to the Cardinals rotation while also being the best starter they've had in awhile, so the gap Cardinals fans thought would exist after losing Montgomery has been filled.

My hope is that the Cardinals take this added depth they got in the Montgomery trade and swing a major deal to improve this rotation further. Whether it's moving someone like Saggese or Roby, or moving someone that they have made more "replaceable", the Cardinals can turn a really frustrating chapter in the history of the franchise into ammunition for their next contending team. Even if they make that deal, I'd probably look back at this Montgomery deal and grade it even higher, as it acted as the catalyst for more moves to come.

There are a lot of things to criticize the Cardinals front office for last year, but they made lemonade from soon-to-expire lemons at the deadline, and it could pay dividends for a long time.