Three Tiers of Trade Deadline Outcomes

The trade deadline is approaching. Deals – more significant than the DFA trade of Genesis Cabrera – could start happening soon.

After a crushing series against the Cubs, there is no denying reality anymore. At 11 games under .500 and 11 games out in the standings as of Tuesday afternoon, the Cardinals are sellers. John Mozeliak confirmed that before their six-game win streak. It’s surely true after mostly uneven play since.

Perhaps “seller” isn’t the right description for their apparent strategy. True, they plan to sell off a decent chunk of their roster. By my count, there are at least 6 players who should be off the roster come August 1^st: Montgomery, Flaherty, DeJong, Hicks, Stratton, and VerHagen. There are an additional 3-4 players who seem likely to be dealt sometime before Opening Day of 2024.

The Cardinals are selling excess parts. But they’re also looking to use those to acquire what they need to contend in 2024.

They are sellers with a shopping list. And how far into that shopping list they get should help us evaluate whether or not their trade deadline moves were a success or not.

We will get into more specifics about possible deals – who stays and who goes – when we chat on Thursday with Belleville News-Democrat Cardinals’ reporter Jeff Jones on the VEB Podcast.

Today, I want to help calibrate expectations heading into the deadline. From my chair, the Cardinals have some of the best talent available among the sellers at the deadline. They should be able to make a bunch of deals — by my count at least 4-6 dependent on how they are able to package players. However, the value of the talent buyers are willing to make available doesn’t match up well with the club’s biggest needs as they try to return to contention in 2024.

Because of this, I want to give you three trade deadline outcomes (plus a bonus worst-case scenario) and I’m going to use classic Cardinal calls to frame them.

There’s the best possible outcome: “I Don’t Believe What I Just Saw!”

A positive and likely outcome: “That’s a Winner.”

And the disappointing one: “So Long from the Ballpark.”

I’ll also give you a worst-case scenario just to round things out and give (some) fans what they want: something to be mad about.

Tier 1: “I Don’t Believe What I Just Saw!”

Gotta start at the top! In a season where just about everything has gone wrong, it’s about time for something to go right. The trade deadline could be that moment. It’s possible, however unlikely, that the Cardinals’ slew of attractive trade options will match up perfectly with the needs of talent-rich contenders, and Mo will be able to bring back just what this club needs to compete again in 2024. What would such a scenario look like? It would take four different acquisitions.

1. A Cost-Controlled #2-3 Caliber Starter

This is the Cardinals’ biggest need if they want to contend in ’24. It’s also the most difficult for the Cardinals to grab. Why is it so unlikely? Because none of their trade pieces match this caliber of player.

Consider Jordan Montgomery. Montgomery came to the Cardinals as a #3 caliber starter with one year of control remaining. He’s now leaving the club as a #3 caliber starter with two months of control remaining. The Cardinals couldn’t trade Montgomery now for what Montgomery was 12 months ago. They certainly can’t improve upon him. Even if they threw in Hicks.

No, the only way to nap a cost-controlled starter in the #2-#3 range is to include a talented cost-controlled player of their own. Maybe that’s Brendan Donovan or, more likley, Nolan Gorman. I’m not sure even Dylan Carlson + Montgomery could bring such a return. Regardless, such a deal seems unlikely, which is why this is an “I Don’t Believe What I Just Saw” kind of outcome.

Alternative: 1 Proven Production Outfielder

If it proves impossible for them to land such a starter, I would also “go crazy” over a cost-controlled outfielder with more proven production than Carlson or O’Neill. I’m comfortable with Walker in RF and Nootbaar in center next season. I would love to solidify the outfield with someone who is a 120-135 wRC+ production lock. Carlson and O’Neill aren’t those players. But they could package either of those players with a pitcher to land someone who has another year or two remaining on their contract. I don’t feel like this option is any more likely than landing a #2-#3 starter. What contender can afford to give up an outfielder of this caliber? Still, having multiple positions on your shopping list does help broaden the pool a little.

2. A MLB-Ready Contender for the ’24 Rotation

This second entry drops the all-important #2-#3 qualifier. The Cardinals need to add to the top of their rotation. They also need to add to the bottom. Once they have that top-end figured out, then it would be a great idea to add another younger arm with the upside to contend with existing arms for the #5-6 rotation spots in ‘24. The Cardinals already have several players who fit this classification, with varying levels of talent and expectations: Matthew Liberatore, Gordon Graceffo, Zack Thompson, and Michael McGreevy. Maybe Andre Pallante. Tink Hence would be a long shot for next season. Adding one more arm to that list — especially one with K potential — gives the club that much more of a chance of a player outperforming expectations. If that doesn’t happen, this kind of player would still provide a K-arm for a bullpen that also needs rebuilding.

Even if Montgomery and a young talent go to land a #2-3 starter, this kind of talent is still gettable. Flaherty could bring back a pitcher on the lower end of that scale. Tyler O’Neill, with a year or arbitration remaining, could net a player a bit better. Paul DeJong’s value might also be higher than expected since he has multiple years of control at a fixed salary.

3. 1-2 Bullpen Contenders

If they don’t sell out acquiring the pieces above, the Cardinals could easily acquire multiple MLB-ready bullpen arms. These acquisitions don’t have to be established arms to make this outcome a success. Lottery tickets with high K potential and good Stuff+ would be ideal.

4. Position Player Depth

Lastly, in an ideal situation, the Cardinals would also find young position player depth who might be able to replace the likes of Taylor Motter and Jose Fermin on the roster in the future. The club has had a knack for turning fringe prospects – like Matt Carpenter, Brendan Donovan, and Juan Yepez – into very useful pieces. I would love to see them turn their tradable talent into players with that kind of profile, even if they are a few seasons away.

Odds of this happening? Very low. >15%.

Tier 2: “That’s A Winner.”

While the upper tier of outcome seems very unlikely, it’s not going to take that to make this a successful deadline. I believe there are very strong odds that they could complete the following deals:

1. A Roster-Lock Starter

Above I argue that it would take packaging a cost-controlled talent along with Montgomery to land a starter with years of control who could slide into the top half of the rotation. What could Montgomery bring by himself?

He could land an MLB-ready starter with at least a few years of control left. Such a player would not fit at the top of the rotation but could slide into the currently empty #4-5 slots.

What kinds of players am I talking about? I’ll give you two options.

AAA/MLB Prospect: This is a player with either enough AAA or MLB production to immediately surpass Matthew Liberatore on the depth chart but probably not enough upside potential as a Gordon Graceffo. I’m hesitant to mention him because he didn’t really work out, but I thinking of someone like Luke Weaver when the Cardinals traded him to Arizona. Weaver had 3.1 fWAR and a 4.10 FIP when he was moved for Goldschmidt. He didn’t have overwhelming talent, but he seemed like a good bet to stick in an MLB rotation going forward. Austin Gomber when he was traded for Arenado might also fit this class.

Arb-Eligible Pitcher: Unfortunately, even those players would stretch the value of rental starters because of their years of remaining control. A more likely outcome would be moving Montgomery for a pricier, arbitration-eligible player who has 1-2 years remaining under control and a solid performance resume. The Cardinals don’t have a lot of players like this, so I’ll frame it this way: What if we traded for the 2017-2019 version of Michael Wacha?

Not exciting. But serviceable. The problem is, again, availability. Can a contender afford to trade us a few years of a Michael Wacha-type for a few months of Jordan Montgomery?

Mo has a difficult task ahead of him.

2. A MLB-Ready Contender for the ’24 Rotation

See above. Even if the best they can do is secure a back-end starter, I would still like them to bring back starter depth in a secondary move. Yes, this is a “throwing stuff at the wall and hoping it sticks” approach to rotation building, but that’s the situation the Cardinals have worked themselves into.

3. 1-2 MLB-Ready Bullpen Contenders

4. Position Player Depth

See the description above for these last two options.

Odds of this happening? This is doable but not easy. 50%.

Tier 3: “So Long From the Ballpark”

This option is not a worst-case scenario but it does represent a loss and it would put Mozeliak in a bind heading into the offseason.

1. Settling for Qualifying Offers for Montgomery and/or Flaherty

It’s possible that the Cardinals simply can’t match up well enough with contenders to get a pitcher with a legitimate chance to improve on existing options for the ’24 rotation. We might feel pretty wary of having Matthew Liberatore in the rotation next year but it’s very difficult to acquire a young player that’s clearly better than him. Even players like Zack Thompson or Andre Pallante come with a hefty price tag because of their years of control.

If this happens, it would make more sense for the Cardinals to keep Montgomery and Flaherty and offer both a qualifying offer (QO). If a team makes a qualifying offer to pending free agents, the player can accept the offer and receive a one-year salary worth around $19.7M. If they deny the offer and sign a contract of $50M or higher, the team gets a compensatory draft pick between the first and second rounds. (Lower if it’s less than $50M.)

Montgomery will deny the QO to pursue a long-term deal. Flaherty is a tougher case, but I think the QO is still an option. His contract history and age suggest he will want to explore the market. Even if he does accept it, the team will still get a #3 caliber starter with the upside of an ace that they need at about the same price such a player would cost for one year in free agency.

Two compensatory draft picks won’t help them win in ’24 or ’25, but it would give them a chance to draft the next Tink Hence or Cooper Hjerpe. The alternative is settling for the next Jake Woodford.

2. 1-2 Cost-Controlled MLB Bullpen Arms

Notice that I dropped the “contender” label for the “bullpen arms” description. If they can’t land a cost-controlled starter, they need to at least secure some bullpen locks for next season. Preferably someone better than Chris Stratton, last year’s cost-controlled bullpen addition.

3. 1-2 MLB Ready Swing/Rotation Arms

In this pitching-poor scenario, the Cardinals can use some of their lesser trade pieces to nab some useful swing arm depth. We don’t want to see another Jake Woodford or Daniel Ponce de Leon in the rotation, but such players have their uses. Maybe they could even find someone with the arm talent of an Andre Pallante in exchange for a Hicks or DeJong.

4. Position Player Depth

See above.

Odds of this happening? Moderate. 35%.

Is there a Worst-Case Scenario?

Yes, I think there is. I know my odds already add up to 100, but there is a slim possibility that the Cardinals explore the market and simply don’t like what they find. It wouldn’t be the first time that the club has taken their ball and went home pouting.

How could such a scenario happen? Well, the qualifying offer is an option for Montgomery and Flaherty. They technically have DeJong under contract for two more seasons at fair market value. If the pitching market dries up, they might decide they will have to use Edman or Donovan in the offseason to acquire a starter. In that case, DeJong could be an acceptable middle infield security blanket. Katie Woo has already reported that the Cardinals aren’t interested in trading O’Neill. Carlson, too, seems unlikely to move now unless Montgomery or Flaherty go with him.

Hicks and Stratton will almost certainly be dealt, but neither player may net controllable MLB talent in return. (Update: apparently the team is looking into an extension for Hicks. Bringing him back at a near-closer level of salary, which is likely what he would demand, removes a trade chip that they could use to help fill out the rotation and adds more budget constraints as the team heads into a very expensive offseason. This would not be a worst-case-scenario move, but I wouldn’t be very happy with it. Paying to secure your bullpen before you address your rotation is foolish. Back to the article...) Buyers prefer to sell from system depth, not their MLB roster. As Mozeliak repeatedly says, costs – returns for the seller – are lower at the deadline. Relievers simply don’t demand significant talent to acquire.

Then there’s the money side of the equation. If the Cardinals can’t improve their roster, they could keep it together and hope for a long-shot winning streak. Keeping fans in the stands means money in their pockets. That’s money they’ll need to turn around to pay for an expensive offseason where they’ll have to acquire up to 4 starters.

While this worst-case scenario is possible, I give it very long odds. The truth is that the Cardinals have some of the best talent to offer on the market. They have a proven #2-3 starter available. They have a young starter heading to free agency with an ace performance in his past. They have a closer-caliber reliever. They have a power-hitting shortstop. They have young cost-controlled outfielders they could move.

It should be a busy deadline. And the Cardinals should be able to get a satisfying result.