5 blockbuster Winter Meetings trades to make the St. Louis Cardinals true contenders

The St. Louis Cardinals have positioned themselves to strike during this year's Winter Meetings.

It remains to be seen how the Cardinals will attack the trade deadline. It's clear they will be searching for bullpen upgrades during the week and the rest of the offseason, but let's be honest, all eyes are on whether or not they'll swing one more "big move" to get this team back into contention.

There are multiple reasons why it makes a ton of sense for the Cardinals to keep being aggressive this next week.

First, the club has already been aggressive all offseason, so why stop now? After coming in last place in the National League Central and being one of the most disappointing teams in baseball, the Cardinals need a major overhaul. They've done some of that "volume" let work that John Mozeliak preached early this offseason, but now is the opportunity to truly put this roster into a much better position.

Second, which is related to the first, their initial offseason moves have cleared the way for them to make another splash. The signings of Lance Lynn and Kyle Gibson provided needed rotation depth and innings, but only Sonny Gray fits the description of a "top-of-the-rotation" starter. They need another guy, and structuring Gray's contract to make just $10 million in 2024 leaves room for that.

They also have yet to make a trade, something that seems to be on the horizon for St. Louis. They have multiple outfield options they need to consolidate, prospects they can attach to them, and even a few middle infielders who are highly coveted around baseball. The Cardinals have all the pieces to make a splash on the trade market and have stated that the Winter Meetings is when they'd turn their attention to trades.

In this story, I've put together five blockbuster trade packages that the Cardinals could swing to make themselves true contenders in the National League in 2024. If I'm John Mozeliak, I'm looking to pull off one of these trades by the end of the week.

The Cardinals' starting pitching issues "Cease"

Cardinals receive: RHP Dylan Cease

White Sox receive: OF Dylan Carlson, RHP Tink Hence, INF Thomas Saggese, and RHP Zack Showalter

One of the names the Cardinals were linked to early in the offseason was White Sox's Dylan Cease. The trade chatter on Cease has grown over the last week, and the Cardinals have been linked to trade talks with them.

Both Katie Woo and Ken Rosenthal of The Athletic (subscriptions required) separately reported that the Cardinals are among the teams interested in Cease. Derrick Goold of the St. Louis Post-Dispatch (subscription required) also confirmed this and reported early this offseason that Cease was a name they would look into. I talked about the potential of a Cease trade (as well as other targets on this list) on the Noot News Podcast, a weekly show I host alongside contributors Sandy McMillian and Andrew Wang.

While it's difficult to know what exactly the White Sox want from a Cease trade, there are a few things we can probably piece together from their GM Chris Getz's public comments and how they've conducted their offseason so far.

The White Sox are looking to blow up their Major League roster, but as they look toward this long rebuild, they need to add talent at many levels of their organization. While I'm sure they'd love guys like Nolan Gorman or Brendan Donovan, I think they'd rather have multiple guys that are a tier below them, rather than putting all of their eggs in one basket.

I could be wrong though, and they may require one of those two to be in a deal. If so, I still probably swing a deal with them, but it would shift how much else I'm willing to give up. But looking at the deal constructed above, I see why the White Sox would be interested.

Thomas Saggese and Tink Hence are the two main chips being sent in this deal. Saggese came over in the Jordan Montgomery trade and won Texas League Most Valuable Player, destroying Double-A throughout the year and earning a late call-up to Triple-A. The Cardinals are extremely high on him, but if they want to hold onto Gorman and Donovan, he likely has to be on the table.

Hence has been their top pitching prospect for the last two years and boasts a very high ceiling, but also a pretty low floor. There are still questions about his durability and ability to go deep into games, and his breaking balls took a step back this year. Hence is still a very valuable prospect though, but if the Cardinals can get a front-line starter now, it's worth the gamble of including him.

Dylan Carlson is the perfect Major League talent for the White Sox to acquire. They are able to grab two highly valued prospects in this deal, while also getting an outfielder who was a top-20 prospect in baseball a few years ago and still has the potential to be a very impactful player. He's a good outfield defender who mashes left-handed pitching, and a change of scenery could do him well.

Chicago's hope here would be that they are getting two soon-to-be very impactful big leaguers and then help turn Carlson back into the player we thought he could be, successfully adding three young talents to their club's new core. Zack Showalter is an interesting bet for them to make as well. He has one of the higher ceilings out of the Cardinals' pitching prospects but remains far away from an MLB debut.

The Cardinals get their second front-line starter to pair with Gray, someone who strikes out a ton of batters and does so while throwing 180 innings a year. Cease was a Cy Young candidate just two years ago and still has two years of control remaining, allowing them to spend on other bullpen arms to round out their club.

As the Gray signing has begun to settle, it's felt like Cease may be the most likely target they have right now. With the uncertain future of their television revenue, Cease gives them an arm that will be very affordable for the next two years, helping ownership weather the storm they are anticipating for the next calendar year or more. Cease also, more importantly, is an upper-echelon talent, and getting him without giving up Gorman or Donovan would be a huge win for the organization.

Cardinals get a high-risk arm with Cy Young upside

Cardinals receive: RHP Tyler Glasnow

Rays receive: OF Alec Burleson and RHP Gordon Graceffo

Tyler Glasnow is probably the most controversial trade target for the Cardinals. Here is the thing though, Goold continues to report the Cardinals' interest in Glasnow, and others in baseball see it as well. It's not just some random idea that fans have, it's something the Cardinals are looking into.

I, for one, love the idea of pursuing Glasnow. He is one of the most talented pitchers in baseball, and the numbers show it:

Tyler Glasnow's 2023 Rankings among starters who threw 120 innings

2.91 FIP (3rd)
2.75 xFIP (1st)
3.08 SIERA (2nd)
121 Stuff+ (7th)
33.4 K% (2nd)
25.8 K-BB% (2nd)

If you're anti-advanced metrics, just go look at the other names at the top of those categories with Glasnow. It's guys like Spencer Strider, Kevin Gausman, lake Snell, Shohei Ohtani, Sonny Gray, Zach Wheeler, Gerrit Cole, etc.

I get it, the injury risk is nerve-wracking. Paying a guy $25 million next year who you're not sure if you're going to get 80 innings or 160 innings from is not ideal. But both of those concerns is exactly why his price to acquire is insanely low for someone as talented (and effective) as Glasnow, and why the Cardinals should be all over this move.

The rotation depth the Cardinals have built with Gray, Gibson, and Lynn helps them to be more aggressive in pursuing a guy like Glasnow. They now have the innings eaters to cover for if Glasnow goes down, but if he is healthy, they have one of the best 1-2 punches in all of baseball.

Giving up Alec Burleson and Gordon Graceffo is not a cheap price to pay, but it's a lot easier than giving up all the assets needed for a guy like Cease. The Cardinals are able to hold onto all of their best young position player (including Saggese) and their top three pitching prospects (Hence, Roby, and in my opinion Hjerpe).

Not only do the Cardinals have the ability to take on the risks associated with Glasnow, but there's actually an opportunity to recoup value from him later that few people talk about.

If things with Glasnow go really well, the Cardinals can look to lock him up long-term, which makes the price they paid for him even more worth it. If they can't reach an extension, they will give him the qualifying offer and receive a draft pick for him in 2025. If he doesn't have the market he was hoping for, he can return on that qualifying offer, and the Cardinals once again have an elite talent for another season.

I'm so in on a Glasnow deal if the Cardinals make it happen. I love the idea of Cease as well, so they cannot go wrong going after either guy.

St. Louis finally makes good on their Juan Soto dreams

Cardinals receive: OF Juan Soto

Padres receive: OF Dylan Carlson, LHP Matthew Liberatore, RHP Gordon Graceffo, OF Alec Burleson

I'll be frank, this feels the least likely of the five blockbusters, but I really wanted to include it because there's reason to believe the Cardinals could explore it (pure speculation at the moment) and it would make this team's offense neck and neck with the Atlanta Braves' historic unit.

First, let's take a quick look at what the Padres appear to be asking for from the Yankees at the moment.

King and Thorpe are much better assets than Liberatore and Graceffo, so maybe including Steven Matz would make sense for the Padres as well to grow their pitching depth. But the chance to move Soto for four players with lots of team control, two being potential rotation pieces long-term and two being impact outfield bats should be intriguing value.

The Padres also move off of Soto's $30 million in this deal, so they now can use that financial flexibility to improve other areas of the roster as well. The Padres need multiple pieces in return for Soto, which is why I think the Cardinals could get involved. They talked with the Nationals about Soto up until the trade with the Padres in 2021, and at that time, the package would have looked something like Jordan Walker, Nolan Gorman, Masyn Winn, Dylan Carlson, and more. Why wouldn't they be interested when the price is far lower?

I know, their rotation needs more help. If they acquired Soto, they would surely move off of Matz and O'Neill, freeing up about $18 million they could use to grab another arm (or even still pursue a Cease deal). Now that they have Gray at the top of their rotation and depth behind him, the pitching staff is closer to league average than the bottom three. And look at this juggernaut lineup they'd be creating:

CF Lars Nootbaar
1B Paul Goldschmidt
LF Juan Soto
3B Nolan Arenado
C Willson Contreras
DH Nolan Gorman
RF Jordan Walker
2B Brendan Donovan
SS Masyn Winn

Um. Yeah. That lineup is insane. While the Padres boasted an elite top-four in their lineup, the Cardinals would have eight different guys who could be 20% better than league average at the plate, with four to five of those hitters having the potential to be among the best bats in baseball. The only team in baseball whose lineup would stack up with theirs is the Braves.

I don't feel great about their pitching, but creating a historic group like this offensively is probably worth it. The Cardinals can then use the rest of the offseason and up until the trade deadline to figure out how to upgrade their pitching staff further, knowing that if they do, they truly are a favorite to win it all.

Even if Soto does not resign, the assets they gave up for one year of him aren't crazy. And honestly, I think their chances of resigning him would be higher than people think, especially if they win.

Think about it, Soto just came from two extremely dysfunctional situations (not just performance issues like the Cardinals had last year, but two clubhouses in need of repair). He'd spend an entire year with high character guys leaders like Nolan Arenado and Paul Goldschmidt, and rub shoulders with a fun, dynamic group led by Willson Contreras, Lars Nootbaar, Jordan Walker, Masyn Winn, and company.

If the Cardinals are going to pay a player, it's someone who is a future Hall of Famer. Soto will be just 26 years old when his new contract begins in 2025. That means any team paying him is getting at least 6-7 more Hall of Fame-level seasons from him, and potentially more. The way he hits is so pure and so elite that it should age as well as anyone can, making him a hitter you can likely trust in his late 30s. And honestly, he's not even going to be 36 until 2035. If you pay him knowing you're probably going to have a top 5 hitter through 2035...even a club like St. Louis could hand out that kind of money.

Do I think it will happen? No, but I think it's a really interesting concept, and one that I wouldn't be shocked to hear the Cardinals join the running for this week.

Free up salary to win the Yoshinobu Yamamoto sweeptakes

Cardinals trade LHP Steven Matz, OF Tyler O'Neill, and OF Dylan Carlson to free up an additional $20 million in salary and target bullpen support.

Sign RHP Yoshinobu Yamamoto to a record contract (prediction of eight years, $235 million plus a posting fee of around $35 million).

The Cardinals are very interested in Yoshinobu Yamamoto. Even if their public posture does not indicate as much, it's been widely reported that privately, they are extremely high on him.

Jeff Jones of the Belleville News-Democrat reported this weekend that even after the Sonny Gray signing, the Cardinals remain interested in Yamamoto and would be willing to go to the expected price range that Yamamoto will be signing for. In an interview I did with Jones on the Noot News Podcast recently, he went further into the connections between Yamamoto and the Cardinals, and that there are people in the Cardinals front office "screaming" for him.

Jones' sources really seem to indicate that the Cardinals are serious about a push for Yamamoto, and if they were to make that a reality, they'd likely need to cut costs through trade.

Steven Matz has been a rumored trade candidate and carries a $12.5 million salary for 2024 and 2025. The Cardinals would not need him with the addition of Yamamoto, so they could move him for bullpen help or prospects. Same with both Tyler O'Neill and Dylan Carlson, who the trio being moved would save the Cardinals about $20 million and give them about $40m-$50m to spend before they even sign Yamamoto.

Assuming they get bullpen help in some of those trades, the Cardinals could use the remaining $10m-$15m of budget to improve the edges of the roster, or more likely, hold onto that space until the deadline where their needs would be clearler.

Getting Yamamoto would be a truly historic moment for the franchise. Not only would they be handing out franchise record contract, but they'd also have a true ace in just his age 25 season. Yamamoto would be huge for the Cardinals in 2024 but also be able to headline their staff for years to come.

Again, the Cardinals have the ability to make a huge move during the Winter Meetings, and doing so would vault them from a potential playoff team to a World Series contender. If the front office keeps their foot on the gas this week, they'll ace the offseason and be ready to compete with the best in the league.