Here is who the Cardinals should target for each of their 5 "to-do list" items

Item #1: Top-of-the-rotation starter

Who they should target: Aaron Nola, Yoshinobu Yamamoto, Dylan Cease, *Sonny Gray

*Sonny Gray will also find his name in item two, but can pass as an item #1 if the rest of the items are strong.

The first order of business for the Cardinals is the most important task of all, grabbing a starter who can lead their rotation in 2024.

Getting three starters who can slot in as their three best guys will do wonders for their ability to win ballgames in 2024, but the quality of their number one starter will set the tone for how legit of a threat they are when it comes to October and beyond.

We can all debate whether or not Aaron Nola, Yoshinobu Yamamoto, Dylan Cease, or Sonny Gray are legit number-one starters in today's game. There is no true "ace" available this offseason, but each of those guys can go toe-to-toe with another team's number one starter can put the Cardinals in a position to win.

Nola feels the most realistic of the bunch, as for a long time now he's looked the part of a Cardinals' front-line starter. He eats innings, knows how to pitch in big games, and carries himself like a professional. If Jim Bowden is right about his contract predictions, he'll be looking at something in the five-year, $125 million range, which is more than manageable for the Cardinals. I could see him getting something in the eight-year, $200 million range if his market really explodes, but I imagine it'll be lower than that number.

Yamamoto would be an awesome target for the Cardinals, and I do believe they'll make a strong push for him, but it seems like other large market teams are really in on him as well. I don't really see them going after Blake Snell, nor do I think he'll prioritize St. Louis as well.

Cease is an interesting name to watch, as I think they should avoid him if he'll require someone like Nolan Gorman, but if they are open to a prospect package instead, I'd be all ears. Cease has the stuff of a true number-one starter and proved it in 2022, but is coming off a down 2023 with two years of control left. He's very valuable, but I'd be hesitant to give up the core bats if I'm the Cardinals.

I'll address Gray further on the next slide, but I don't think it's a terrible thing if he ends up being their guy from this tier. What it would mean though is they have to get a really good second starter as well, and probably an overqualified third starter to add to the mix to compensate for missing out on the top guys available.

Item #2: Second front-line starter

Who they should target: Sonny Gray, Tyler Glasnow, Jordan Montgomery, Eduardo Rodriguez

The Cardinals have to be extremely aggressive with the top two starters they acquire. They need a one-two punch they can rely on in October, but it's also part of building a strong regular season club as well. Having two guys you can rely on every fifth day to pitch at a high level takes a lot of pressure off the rest of the rotation, puts less milage on the bullpen, and helps the lineup have room to breathe and not feel like they have to score 8+ runs a game to win.

Sonny Gray feels like the perfect guy for this spot, as he has been one of the best pitchers in all of baseball the last two seasons and has been a top 15 pitcher in baseball since he came into the league. He'll be 34 before the start of the 2024 season, so regression is expected, but even so, he'll still be more than capable of being a number two starter. He's likely going to finish second in AL Cy Young voting this year, and was 54% above league average when it came to ERA+. Gray wants to be closer to Nashville and is looking for a short-term deal, so it seems like a perfect fit.

Glasnow would be an excellent addition for the Cardinals, and honestly, my perfect offseason has them signing their number one and two starters while trading for Glasnow as well (more on that in a future story). Glasnow has injury risk and a large $25 million salary for 2024, meaning the cost to acquire him should be significantly less than the talent he has.

In a contract year, Glasnow is going to want to prove he's worth a long-term deal, so I expect him to be on the field as often as possible. Even if you only expect 20-23 starts from him, that's still a massive upgrade to the rotation, and if he's healthy in October, he's a legitimate weapon against any offense.

A reunion with Montgomery could be in the cards, as he's continued his great form since being trade from St. Louis and has been a key contributor for the Rangers on their way to a potential World Series title. Rodriguez is another guy with World Series pedigree, and has been really good in Detroit and will be looking to cash in this offseason.

Item #3: Third starter who can slot ahead of Miles Mikolas and Steven Matz

Who they should target: Shane Bieber, Edward Cabrera, Bryan Woo, Shota Imanaga, Braxton Garrett, Lucas Giolito, Seth Lugo, Kyle Hendricks, Wade Miley, Frankie Montas, Tyler Mahle

This list is long and will be dictated in large part by the names they acquire in the first two items on this list.

The Cardinals could look to bring in a former Cy Young winner who's lost a lot of stock in the last year in Bieber. He's not the same guy anymore, but as your number three starter, I think you like what he has to offer and can also bet on him as a guy who bounces back in a contract year. Like Glasnow, the price to acquire should be relatively low, making him even more attractive of a trade candidate.

On the free agent market, Shota Imanaga is a left-handed starter from Japan coming over this offseason with strikeout stuff. He'd be a really solid third option for the rotation should St. Louis sign him. Kyle Hendricks, Wade Miley, and Seth Lugo all had solid years in 2023 but would present pretty low ceilings but could fill that third rotation spot if needed.

On the trade market, arms with control like Woo, Cabrera, and Garrett all offer varying levels of upside but should be able to fill that number three role with almost no problem. Cabrera would likely take the least trade capital to acquire of the three, and the Cardinals should balk at any requests for their best young bats when in conversations surrounding these guys.

Montas and Mahle are both injury bounce-back candidates, while Giolito's awful end to 2023 may force him to take a flyer deal to prove his value again.

This list has the widest range of talent, but it really does come down to what the Cardinals are able to do at the top of their rotation, and how the market unfolds. I feel good about them getting three really good guys to lead their rotation, but it's still too early to tell how the market is going to play itself out.

Item #4: High-leverage reliever via free agency

Who they should target: Yuki Matsui, Jordan Hicks, Shelby Miller, Robert Stephenson, Reynaldo Lopez, Liam Hendricks, Brett Suter

When it comes to relief options on the free agent market, there are a variety of names the Cardinals could add to their bullpen that would help create a dynamic group for St. Louis in the highest-pressure spots.

Yuki Matsui is heavily linked to the Cardinals and is the youngest player to ever hit 200 career saves in Japan. He's got great strikeout stuff even though he doesn't throw hard, and should not require a large contract to bring into the fold.

A reunion with Jordan Hicks or Shelby Miller would make a ton of sense too. Hicks really found his grove as a closer for the Cardinals during the summer months before being traded to Toronto for their stretch run. He has some of the best stuff in all of baseball and is still young as well. Miller has enjoyed a career resurgence as a reliever, posting a 1.71 ERA in 42 innings for the Dodgers this year.

Robert Stephenson, Reynaldo Lopez, Liam Hendricks, and Brett Suter would all provide various levels of experience to the Cardinals bullpen, and each of them are guys they could trust in big spots. Josh Hader is far and away the best reliever on the market, but I just doubt the Cardinals would give him the kind of contract he is going to get this winter.

If the Cardinals can focus on one of these relievers on a short-term deal with not a crazy high AAV, it would still allow them to make all of the other moves they need to make while strengthening their bullpen in the process.

Item #5: High-leverage reliever via trade

Who they should target: James Karinchak, Garrett Crochet, Daniel Bard, Jason Adam, Carlos Estevez, Justin Lawrence

This list is hard to predict at this stage in the offseason, but with the amount of ancillary pieces the Cardinals have on their roster, they should be able to add bullpen help through trade as well.

Tyler O'Neill, Dylan Carlson, Luken Baker, and Andrew Knizner all feel like candidates here for a trade, where the Cardinals could get a valuable reliever in a straight swap. They could also choose to use a prospect instead to acquire an arm.

James Karinchak would be an interesting name to watch in my opinion, as the Guardians have two years left of control on him and could capitalize on his value this offseason by moving him. All of these relievers are purely speculative at this point, but could fit the bill as one of the Cardinals' four high-leverage relievers.

If the Cardinals can grab a guy from each of these categories this offseason, they'll have accomplished what they needed to in order to put the club back into contention. Not just for a division title, but to be an actual threat in October. Time will tell if the Cardinals can make this plan a reality.