Ryan Helsley
Destinations: Baltimore Orioles, Toronto Blue Jays, New York Yankees
If the Cardinals are not going to contend in 2025, having an elite closer does not necessarily do them a whole lot.
Sure, they could extend him long-term, but extensions are a really tricky thing for relievers who will want as much money as Helsley will, which gives me doubt that one could happen between the two sides, especially if the Cardinals are cutting payroll.
Instead, the Cardinals can maximize Helsley's trade value this offseason and help infuse their farm system with even more young talent. Big trade packages have been given for elite closers in the past, and I could see the Cardinals really benefiting from what clubs can offer them this offseason.
The Baltimore Orioles make a ton of sense here. They have a deep farm system that they can tap into, and Baltimore has plenty of young bats, which are needed by the Cardinals. Their championship window is wide open right now and strengthening their bullpen could really help them in October. Their bullpen has been one of their weakest spots in recent years especially.
While the Toronto Blue Jays disappointed like the Cardinals this year, it is widely expected that they look to shuffle their roster in an attempt to compete in 2025. The Cardinals and Blue Jays have become frequent trade partners in recent years, and Toronto has shown interest in Ryan Helsley in the past. They too could use a major bullpen upgrade as they look to compete in the American League East.
While there are plenty of clubs who would make a call on Helsley, I threw one more American League East team on this list, the Yankees. Like the Blue Jays, the Cardinals have made many calls with the Yankees over the last few years, and no matter what happens this year, they are going to be right back in World Series mode in 2025. Helsley would be a major upgrade for the back end of their bullpen next season, especially as they prepare to lose Clay Holmes and Jonathan Loaisiga.
While the three veterans I mentioned earlier seem unlikely to be moved unless they indicate they would like to be elsewhere next year, Ryan Helsley screams trade candidate to me for the reasons I listed at the top. Many argued he should have been dealt at this past trade deadline as well. The Cardinals need to capitalize on his value this offseason as they themselves look to reset, and it would probably help Helsley to be in a winning situation next year as he approaches free agency.