10 bold predictions for the Cardinals trade deadline and second half of the season

The St. Louis Cardinals are back from the All-Star Break, but unfortunately, are not in the position that many of us thought they would be this year.

If you had asked me what "worst case scenario" for this time was in Spring Training at the All-Star Break, I could have seen them being around .500 or a few games below, but like past trade deadlines, just needing to add some timely arms to propel them to contention. Honestly, I thought they would be looking to add an impact arm to try and compete with the Dodgers, Braves, Mets, and Padres.

Well, technically they are still competing with the Padres and Mets...but for the most disappointing team in baseball.

The second half of the Cardinals' 2023 season is going to look vastly different than past years. Sure, the Cardinals have missed the playoffs in recent memory, but they were never truly declared out of the race this early. St. Louis has dealt off assets at deadlines before, but never names as big as we could see this season

There are going to be a lot of storylines heading into the rest of the season worth watching. It may be tempting to think it's time to turn off the television until next spring, but there are a lot of things of importance still. Moves to be made, young players to watch, position battles to monitor, leadership changes, individual milestones, and more.

While we all want to see the Cardinals in the playoffs every year, there is still a lot of value in following a club that is laying the groundwork for a turnaround next season. In all honesty, this kind of season may be exactly what this organization needed to get things right for the next five years of baseball, and if that is the case, I can bear one season of extreme disappointment.

Here are 10 predictions for the Cardinals second half of baseball

1. Jordan Montgomery, Jack Flaherty, and Jordan Hicks will all be dealt at the deadline, yielding great assets in return.

I've seen people speculate that the Cardinals could look to extend any of these three, or just give them a qualifying offer in the offseason to get draft pick compensation. I would bet that we see all three traded away before the deadline.

Why? Well first, John Mozeliak himself said they are going to trade people and left very little doubt that some of those people will be their impending free agents. He told me back in early June that they could look to capitalize on the value of their impending free agents if things did not turn around, so they've been preparing for this scenario for a while now. Second, he has indicated that they aren't concerned with getting draft pick compensation.

The Cardinals could go out and pursue a reunion with any of those three in free agency this offseason, but keeping them on the roster gives them little to no edge on their competition this winter when it comes to signing them. All three are going to look for the best possible contract they can get, and if St. Louis trades them away and then outbids the rest of the market, I'm going to guess that they will be willing to come back.

Third, which I think is the most important reason, is that all three are going to have a lot more value on the trade market than you would expect. Take a moment to go on FanGraphs RosterResource and sift through the rotations of every contender. All of them need starting pitching, and both Montgomery and Flaherty would be major upgrades for them. Hicks will also be coveted by many of those contenders.

I can see both Montgomery and Hicks netting the Cardinals a top-100 prospect in baseball in separate deals, or very intriguing assets for the future of their club or to use in trades later down the line. Flaherty should also net them a good return, as the pitching market is so thin right now that all three arms will be some of the best available.

Other GMs, like Kim Ng of the Miami Marlins, have already stated how much of a seller's market this is. Players are going to come at a premium, which will work greatly in the Cardinals' favor. This should really help jump-start a retool for the 2024 season.

2. Adam Wainwright gets to the 200 win milestone

I almost did not predict anything regarding Adam Wainwright, as it is still just hard to watch how things have unfolded for him this season. With at least two rotation spots opening up at the deadline though, I think Wainwright will get his chance to get his 200th win.

Wainwright is only two wins away from the milestone, but it won't be easy to achieve, and it may be a painful road to get there. John Mozeliak has been very candid about Wainwright now having a long leash anymore, so if his play on the field does not become at least defensible, this prediction could fall flat.

The Cardinals will likely want to give opportunities to other arms they have as well. If they trade for any controllable arms, they'll need innings. The likes of Matthew Liberatore, Michael McGreevy, Gordon Graceffo, and even Dakota Hudson could see some starts as well. Wainwright will need to give the Cardinals a reason not to remove him from the rotation unless they move to a six-man rotation.

3. Brendan Donovan will finish top-20 in MVP voting

Here is me taking a big swing here predictions-wise. Brendan Donovan has been really good over the last month and a half of baseball, and if he continues that into the second half, he has to be considered one of the best players in the National League.

No, Donovan isn't a superstar, but he's playing like the best possible version of a guy who just misses being a part of that conversation. Look at how Donovan has heated up as the months have gone on.

There's been a noticeable uptick in production each month from Donovan, and even if his numbers "regress" back more toward what they were in June, he's an extremely valuable player. How many guys can have an .845-.943 OPS while playing six different positions throughout a season?

There's a reason why the Cardinals want to hold onto Donovan, and why the rest of baseball really wants him. I think an MVP voter or two will catch onto that after a strong second half from Donnie.

4. One of Tommy Edman, Dylan Carlson, or Nolan Gorman is traded for controllable starting pitching

The Cardinals have already stated that Lars Nootbaar and Jordan Walker are off the table, but they also have interest in acquiring a pitcher from Seattle (namely Logan Gilbert), and have other young arms on their mind. While they could acquire some arms through "selling moves", it'll likely take an aggressive move using one of these names to get a quality young arm.

My prediction is that one of these three names is traded to the Seattle Mariners in a deal for an arm like Gilbert, Bryan Woo, or Bryce Miller. The deal would likely have to revolve around Gorman or Edman.

I think there is an outside shot that Donovan could be the name moved, but as I stated in the last slide, I think the Cardinals see him breaking out and would rather part with one of these other names instead.

Losing any of their young bats would hurt, but it's necessary if the Cardinals want to make a splash for a young arm.

5. The Cardinals will play above .500 baseball during the second half

I honestly think the clubhouse is going to feel a breath of fresh air in the clubhouse with the moves the Cardinals will be making. Those who are not traded know they are in the Cardinals' plans for 2024 and can begin to build this team back up together during the second half.

While I do not expect the club to be really good the rest of the season, I do think they'll stabilize their play more and look more like the team they should.

This will be especially true if they are able to acquire some of those new young arms they need. If they mostly just sell, it may be difficult to find enough innings to really win enough games. But honestly, if this prediction falls flat, I think the Cardinals will be just fine next season.

6. Masyn Winn makes his MLB debut

If one of the Cardinals' young bats is dealt, a path for Masyn Winn to join the Major League roster because very real.

After a really slow March and April for Winn in Triple-A, he stabilized himself with a .799 OPS in May and .763 OPS in June, while exploding to slash .306/.375/.556 during the course of July.

The Cardinals have cracked the door open once again on the shortstop position by giving Tommy Edman an extended run in center field. If he is dealt at the deadline, that door really swings open, but if not, I still think there is a good chance Winn can pick up reps in the middle infield. Edman is also dealing with a wrist injury right now, so he may be down for a bit.

Paul DeJong also has potential to be dealt at the deadline, with a number of contenders needing shortstop help.

Winn would be a great player to have on the club for the remainder of the season to see what he offers the club, get his feet wet, and be ready to take over full-time on Opening Day in 2024.

8. Willson Contreras maintains a hot bat, but his role as a primary catcher remains a major question mark for the 2024 season and beyond

It's kind of amazing to see how quickly Willson Contreras' numbers have bounced back in the last month or so. It wasn't all that long ago that he was batting around .200 with no power, but he has raised his OPS up to .753 thanks to a 1.797 OPS in July.

While there is no way Contreras' bat is that hot to finish the year, I do think he has found his groove once again as one of the best-hitting catchers in baseball, which will be a huge boost to the Cardinal lineup. They need his bat to play.

What I do think will remain a big question mark after this season is his ability to be the man behind the plate in 2024 and beyond. No, I don't see a full-on transition to DH or the outfield coming, but I do think it's very possible the Cardinals go into 2024 with Contreras and Herrera splitting time, and Contreras DHing on games when Herrera is behind the plate.

For as bad as the Cardinals pitching staff has been, Contreras does receive blame for how rocky things have been defensively for him. I'll link my recent story on his defense here, but it hasn't been pretty, and it is costing the Cardinals.

Perhaps another offseason working with the coaching staff and pitchers will improve things, but for now, I see Contreras being a question mark defensively for 2024.

9. Tyler O'Neill is traded, has a great second half with his new team

Tyler O'Neill is set to return from his rehab assignment this week, but I do not think his time in St. Louis will last very long. And no, it's not because of another injury.

Here is my prediction. Tyler O'Neill and Jack Flaherty will be traded to the New York Yankees for right-handed pitching prospects Randy Vasquez and Clayton Beeter. Beeter has already been identified as a player the Cardinals will be interested in at the deadline, and the Yankees could use both outfield help and another arm for their rotation.

The Yankees don't need to take a swing for a "huge" arm, Flaherty would likely slot in as their number four or five starter which is perfect for them. O'Neill gives the Yankees another bat for their lineup that really needs one right now.

I believe O'Neill will find success in New York or whatever club he is dealt to. He is a year away from free agency, and I am sure he is motivated to prove all of the doubters wrong and secure a big payday next offseason.

10. The Cincinnati Reds strong finish to 2023 forces the Cardinals to be aggressive during the offseason

The Cincinnati Reds are an extremely fun team to watch. Elly De La Cruz, Matt McLain, Jonathan India, Spencer Steer, and others along with a farm system that still has more talent on the way. The Reds are ready to start contending.

The Cardinals can see this. They have a few advantages over the Reds with their bigger payroll, as well as having already established starts that are being supplemented with young talent. This season, the Reds have the edge, but you better believe St. Louis is going to punch back next season.

The Cardinals can take control back of the NL Central if they indeed make aggressive trades at the deadline and in the offseason, along with spending the necessary dollars in free agency to make a major pitching upgrade. It probably doesn't feel like this team can overcome the Reds right now, but I have a strong feeling the Cardinals see them as a legit threat and are planning accordingly.

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