Which Cards are likely to move at the Deadline?

July 27th, 2023

This story was excerpted from John Denton’s Cardinals Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

There’s anticipation heading into this weekend, but not for the reasons many expected prior to the season, when the Cardinals were believed to be far and away the best team in the NL Central again.

This weekend will feature the rival Cubs’ only foray to Busch Stadium this season after the two squads faced off in London in late June. By most preseason prognostications, this four-game set against Chicago would have been the weekend when St. Louis started to methodically separate itself from the likes of the Cubs and Brewers -- just as the club did last season in early August before the Cards became runaway champions of the NL Central.

This time around the excitement is much different. Now, the focus is on which Cardinals may soon be leaving town before the Trade Deadline and what will be the return haul for a rebuilding club already casting its focus to 2024, rather than a repeat run at the NL Central crown this year. The Cards are in the odd position -- for them, at least -- of being sellers instead of buyers before Tuesday's Deadline. 

Well, the Cardinals are kind of, sort of sellers, but not of the fire sale variety. They still have every intention of trying to compete in 2024, meaning they will keep Paul Goldschmidt, Nolan Arenado, Jordan Walker and Nolan Gorman around and will likely only want returns of Major League talent or prospects who have a shot of breaking into the big leagues by next season.

With numerous valuable commodities, the Cardinals should be extremely active in the coming days. However, some of the trade possibilities could still be around long after the Deadline. Here are three questions the Cardinals will be facing in the coming days.

If the Cardinals desperately need pitching, why are they most likely trading away pitching? Will they deal Jack Flaherty and Jordan Montgomery?

Flaherty and Montgomery have alternated between being the Cardinals’ most reliable starters this year and their most frustrating assets. Both will be free agents in the offseason, and the Cards would rather deal them now for a multi-player haul than risk losing them for little more than a compensatory Draft pick this winter.

There are a couple of caveats to the pitching scenario, however. St. Louis learned long ago that nothing will keep Montgomery from testing the free agency waters, and his camp is looking to fully maximize his value -- both in terms of years and dollars. A trade of Montgomery will almost assuredly come in the next few days, likely to a team willing to include multiple pitching prospects.

Flaherty, who pitched well over five innings on Wednesday in Arizona, might not be on his way out of town just yet. The Cardinals are still holding out hope that an 11th-hour long-term extension can be reached before Tuesday, according to a source familiar with the club's thinking. 

Despite years of fan speculation that Flaherty, a Southern California native, would likely jump at the chance to leave St. Louis for the West Coast, the franchise is still of the belief that Flaherty covets the opportunity to pitch for the Cardinals. The two sides have made little progress toward an extension in recent days, but the Cardinals are expected to make one more contract extension run at Flaherty before the Deadline, a source confirmed. If that fails, the Cards will likely be forced to deal Flaherty.

Left-handed pitcher Steven Matz, who has gone a long way toward changing the trajectory of his season in recent weeks, could be had for the right price too, but the Cardinals are somewhat leery of unloading him because he is under contract for two more seasons at a relatively decent salary, a source said.

With two closers still on the roster in Jordan Hicks and Ryan Helsley, who stays and who goes?

No Cardinal has turned around their standing within the organization more this season than the immensely talented Hicks. He was one of the team’s most ineffective and infuriating pitchers early in the year when he could hardly be trusted in any kind of high-leverage situation. These days, however, he’s saved eight games and he is riding his 103-mph stuff to prove one of the most trusted pieces out of the ‘pen.

Like with Flaherty, the Cardinals are working to lock up Hicks to an extension, and they figure to make him another offer before Tuesday’s Deadline, per a source. As for Helsley, who was recently transferred to the 60-day injured list, the franchise is concerned about his history of arm injuries and his lingering unhappiness over losing his offseason arbitration hearing will likely try to trade the former All-Star in the coming days or in the offseason.

Which outfielder is most likely to be gone?

The Cards had to endure a sort of nightmare at the MLB All-Star Game a few weeks back when Randy Arozarena and Adolis García -- former Cardinals prospects moved to other teams -- showed off during the Home Run Derby in the Midsummer Classic. Back when the pair was in the Cards’ system, the club rated Harrison Bader and Tyler O’Neill ahead of the pair of future All-Stars -- just as St. Louis did with Flaherty over Sandy Alcantara and Zac Gallen -- and it doesn’t want to make that mistake again.

With that in mind, the Cardinals aren’t yet willing to give up on the oft-injured O’Neill, who of late has shown why he is still so intriguing with his combination of speed and defense. Instead, the Cards are much more likely now to deal outfielder Dylan Carlson, an immensely talented outfielder who might someday hit 25 home runs in the right environment. More teams will ask for Brendan Donovan and Tommy Edman, but the Cardinals are more willing to move Carlson, Alec Burleson or even shortstop Paul DeJong, a source said, in a potential package with Montgomery for pitching prospects.