Ryan Helsley, the standout closer for the St. Louis Cardinals, is without a doubt the team’s most sought-after player.

The two-time All-Star was playing at his best by the end of 2024. With 49 saves, Helsley surpassed Trevor Rosenthal’s 2015 season record of 48, shattering the Cardinals’ single-season saves record. Helsley was named the Trevor Hoffman National League Relief Pitcher of the Year by the National League for his 49 saves, and he is currently on the All-MLB Team. At 30, Helsley is at the height of his abilities. Helsley is at the peak of his game right now because relievers have short careers and clubs depend on their best efforts.

If the veteran players agree to waive their no-trade agreements, the Cardinals hope to trade them off. In order to make room on the roster for the younger players in the depth chart to play every day, the team wants to cut larger contracts. Helsley does not have a no-trade clause, and many other teams will want to acquire him because he is one of the top closers in the game.

A player of this caliber who can shut down any lineup to secure victories should be in high demand. In addition, he is cost-controlled, earning $8.1 million in 2025 before entering free agency. This creates a situation where the Cardinals can rent him out and use his value to add more prospects to the depth. Fans will recall Aroldis Chapman’s 2016 trade to the Yankees for Gleyber Torres and his 2023 trade to the Cole Ragans.

However, unless they are blown away by a trade offer, the Cardinals are now hoping to retain Ryan Helsley for the 2025 season, according to a recent report from Derrick Goold of the St. Louis Post-Dispatch (subscription needed). On the surface, it appears that the Cardinals are unwilling to make the correct move—moving Helsley in a desperate way. In a complete reconstruction, they are unable to sell off the entire roster. Rather, in this process, they are choose to be extremely choosy. But are the Cardinals seeing a chilly market for Helsley now that this story has been released and the Winter Meetings are drawing near?

Trade negotiations need to be stepping up right now given the situation, as Helsley is currently the game’s top closer on a cost-controlled contract. Helsley would be connected to any side hoping to make a big splash this off-season. However, this indicates to me that the Cardinals’ asking price is outrageous when compared to what other teams believe his market value is. The Cardinals have every right to make their asking price as high as they can, but Helsley’s trade market is now unsuitable.

The St. Louis Cardinals should be quite busy in the coming weeks as the Winter Meetings draw near. Fans in St. Louis are about to witness a new era as the roster reset gets underway. Many familiar names will remain during this historic 2025 season, even though a number of players will be traded to other teams. What will happen with Ryan Helsley is the last unanswered question for the Cardinals during the off-season. Will he result in the off-season’s largest trade? Or will he be held until the deadline for the trade? Will the Cardinals offer him a contract extension worth $100 million? The issue surrounding Ryan Helsley should become clearer at the 2024 Winter Meetings.

If Blake Snell signs elsewhere, Jack Flaherty may be forced to step into the Cardinals’ worst-case scenario.

At the MLB trade deadline, the Los Angeles Dodgers acquired Jack Flaherty from the Detroit Tigers, and they haven’t looked back. Both in the last innings and during the MLB Postseason, Flaherty gave the Dodgers vital innings. Flaherty had a 3.17 ERA and 3.1 WAR in 2024 while pitching for the Tigers and Dodgers. With that type of production, it’s difficult to dispute.

Even though Flaherty won a World Series, there is no assurance that he will return to Los Angeles. Particularly when the Dodgers signed Blake Snell on Tuesday night, Flaherty’s performance might have cost him a spot with his home team. Snell’s contract is for $182 million and has a five-year term. Even if some of that money is in deferrals, it’s still a lot of money.

In addition to providing Snell with a new home with the World Series winners, his deal allowed him a sneak peek at the free-agent pitching market. Pitchers like Snell, Corbin Burnes, and Max Fried are extremely expensive because there aren’t many top-tier starters available. With someone like Flaherty getting more than Spotrac’s projected AAV of little more than $21 million, that shift should be widespread.

If not with the Los Angeles Dodgers, where will Jack Flaherty end up? The Cubs, why not?

Apart from not being in LA, where does that leave Flaherty? There are numerous teams who require starting pitchers, but there aren’t many elite rotation players to cover those shortages. It makes a lot of sense for Flaherty to join a franchise like the Chicago Cubs, whom he knows from his days with the St. Louis Cardinals. Chicago and Jed Hoyer won’t outspend other teams at the top of the market, but they could be able to prioritize a pitcher like Flaherty right away.

Flaherty’s record versus the Cubs is 3-4 with a 3.67 ERA in 17 games. Although he isn’t the ace that many north side supporters are searching for, Chicago is familiar with his work and can offer excellent depth behind Shota Imanaga and Justin Steele.

In addition to being an excellent opportunity to exact revenge on the St. Louis Cardinals, it’s better than nothing.