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.

When the Cardinals made the bold decision to deal Jordan Montgomery to the Rangers in late July just before the MLB Trade Deadline, both sides said all the right things about a potential reunion in St. Louis after the talented lefty starter became a free agent.

But how realistic is that now after Montgomery repeatedly showed off his grit and solidified himself as a big-game pitcher while leading the Rangers to their first World Series title? Not only did he go 4-2 with a 2.79 ERA down the stretch as the Rangers qualified for the playoffs, the 6-foot-6 hurler with the heavy sinker impressively compiled a 3-1 mark in the playoffs, including Game 1 wins over the Rays and the Astros in the AL Wild Card and Championship Series, respectively.

Without question, the price of doing business between Montgomery and the Cardinals is going up following the prolific postseason that he authored. On the day he was traded from the Cardinals to the Rangers, Montgomery gave a bit of insight into the frustration he felt throughout the year over the Cardinals never approaching him about a contract extension prior to last season. He will most definitely be listening when the pitching-seeking Cardinals come calling in the next few weeks, but this time around, he will be holding all the leverage while likely seeking a deal exceeding $100 million.

“Yeah, but we would have just had to get the talks rolling,” Montgomery said regarding no contract extension ever coming last winter. “But we can always do it again in free agency.

“[The Cardinals' front-office members] are great and this is a great organization. I’m not going to burn any bridges with great people. So, there’s always an opportunity.”

To the surprise of most industry experts, the Cardinals cleaned up in the June 30 trade with the Rangers that centered around Montgomery and reliever Chris Stratton. In addition to landing steady left-handed reliever John King, the Cardinals also got Arizona Fall League All-Star pitcher Tekoah Roby and Texas League MVP Thomas Saggese to restock their farm system with talent.

While those pieces will likely help the Cardinals down the line, the franchise’s hopes for returning to contention in 2024 will hinge on adding starting pitching this offseason. As counterintuitive as it seemed at the time, a Cardinals franchise already thin on pitching dealt away five pitchers prior to the Deadline. Former ace Jack Flaherty and former closer Jordan Hicks, along with left-hander Génesis Cabrera, were also dealt in a three-day flurry by a Cardinals organization not accustomed to being sellers at the Deadline.

In the days, weeks and months ahead, the Cardinals will work to put the pitching pieces together for a staff that can restabilize the franchise. With Miles Mikolas and Steven Matz as the only firm starters still under contract, the Cardinals ideally need to land three starters for next season. But doing that is a humongous ask, especially when their bullpen needs retooling as well. A more likely scenario would seem to be signing two starters, adding a couple of bullpen arms and locking in hard-throwing lefty Zach Thompson as a starter for next season.

That brings the Cardinals back to Montgomery, the pitcher they shockingly landed from the Yankees in August 2022 and who won his first four starts while wearing the birds on the bat across his chest. However, the team passed over Montgomery as a starter in its Wild Card Series loss to the Phillies and it saw him struggle through a winless 10-start stretch in '23.

He came out of that run by proclaiming this when MLB.com asked him about the kind of winless skid that might have rattled most pitchers: “I am not a loser!” He then backed that up by winning four of his next five starts, then a month later heading to Texas and leading that franchise to heights never seen before.

When asked in late July to sum up what would stick with him from his one-year, two-season stint in St. Louis, Montgomery said: “Just all the new people I met and friendships I made and the quality of the people around here.”

Would Montgomery be up for a reunion with the Cardinals -- this time as their front-of-the-rotation starter? It certainly seemed like he would back in late July. But, clearly, the cost of making that happen will be a steep one for the Cardinals after the way the soon-to-be 31-year-old lefty pitched while helping the Rangers win the World Series.