3 trade packages to reunite the St. Louis Cardinals' with former ace Jack Flaherty

Package #1 for Jack Flahetry

I said it in the intro and I'll say it again, all of these deals are going to hurt. They have to in order to pry Flaherty away not just from the Tigers, but from being added to a different contender in pursuit of him.

Just off the top of my head, any of the Dodgers, Orioles, Guardians, Brewers, Braves, Padres, Red Sox, Yankees, and Astros could be looking to add Flaherty as the deadline gets closer. Pitching is always in need at the deadline, and with how good Flaherty has been, he is going to be the hot name on the market outside of Crochet and Skubal.

Flaherty is in the 94th percentile or higher in Whiff%, K%, BB%, and breaking ball run value this season. He has regained his elite strikeout stuff while also fixing his walk issue and being among the best in baseball at preventing free passes. Not only that, but he's well above average in creating weak contact as well, and has been a good groundball pitcher when he does not get a swing-and-miss.

Everything about Flaherty's game this year has been good, and so teams are going to be willing to pay up for the 28-year-old stud.

Giving away Cooper Hjerpe would be extremely painful. To me, he is one of the most underrated pitching prospects in baseball, and I would not blame the Cardinals for saying no to offering him. Frankly, I have a hard time saying I would either. Hjerpe's deceptive delivery and arm angle allow his low-90s fastball and nasty breaking stuff to play up even more, resulting in a 35.1% strikeout percentage across High-A and Double-A this year. He's already had two starts this year where he allowed no hits before being pulled due to his pitch limit. Hjerpe has so much potential.

But again, the Tigers are going to want something impactful for Flaherty, so if they used someone like Hjerpe as the centerpiece along with a high-upside prospect in Leonardo Bernal and MLB-ready infielder in Cesar Prieto, that could get the job done.

I could another team sending a stronger offer than this, but this would be really stretching for St. Louis. If you don't like this deal, I have two others that would be very difficult to make as well but could be realistic.

Package #2 for Jack Flaherty

Remember how I compared the price for Flaherty to the price for Montgomery? Well, maybe that could be the literal price in this case.

Let's take a moment to compare the numbers from Flaherty so far this year and what Montgomery put up with the Cardinals before being dealt.

I remember at the time making the point that Montgomery could fetch the Cardinals two top 100 prospects with his performance, especially since he'd likely be the best rental arm available. While Max Scherzer and Justin Verlander were both moved as well, both trades took the Mets eating significant money to get good value in return. Montgomery did not require anything like that.

That was a pretty basic comparison of the two starters, but if you go through their entire bodies of work before being dealt away, Flaherty was been the far superior pitcher. Expecting him to be traded for less than what the Cardinals got for Montgomery seems silly to me.

If you just don't think it is worth making the deal, that's fair, and I understand why you feel that way. But if the Cardinals want to get a deal done for Flaherty, it will take a strong offer like this.

Thomas Saggese continued his dominance in 2023 after being traded to St. Louis, winning Texas League Most Valuable Player and earning a promotion to Memphis. Things have been rockier this year for Saggese, but his bat seems to be heating up a bit, and he is still a very promising infielder long-term who could help the Tigers' awful offense very soon.

Tekoah Roby has dealt with an injury this year, the second straight season where he's been sidelined for significant time. Unfortunately, in the few starts Roby has been healthy this year, he has not been nearly as effective as in years past, but once again, he's still a very intriguing prospect, and like Saggese, snuck on top 100 lists during the preseason.

Both players have fallen off almost every national top 100 list this year, but they are still borderline top 100 talents like they were at the time of their trade last year. With the Cardinals' organizational depth in the middle infield and other intriguing arms they value over Roby, they could be convinced to part ways with these two.

I decided to fully replicate the Montgomery trade by adding another piece for St. Louis in here, getting them outfielder Mark Canha. With Tommy Edman's rehab being hindered once again, it feels likely that St. Louis will add another right-handed bat to the club. On the season, Canha is slashing .286/.403/.476 in 77 plate appearances against left-handed pitching, resulting in a 145 wRC+. The Cardinals desperately need production against lefties right now.

In turn, I added Zack Thompson into the deal, who like Saggese and Roby, has had a down year but still has upside moving forward as a back-end starter or impact reliever.

Package #3 for Jack Flaherty

I'm making deals here that I think the Tigers would accept, that I think could outbid the market, and that I could potentially see the Cardinals doing. Even though this could come back to bite them, I could see the Cardinals offering Ivan Herrera in a straight swap for Jack Flaherty.

Here's how I got here. I'm sure the Cardinals do not want to move their big league bats like Lars Nootbaar, Nolan Gorman, Brendan Donovan, or Alec Burleson to grab pitching at this deadline, and I highly doubt they'd move Jordan Walker either. Frankly, all of them would be massive overpays to offer for Flaherty in my opinion.

Second, I'm sure St. Louis would love to avoid giving away multiple of their favorite prospects as well. The guys I really think they would have a hard time parting with are Tink Hence, Quinn Mathews, Victor Scott II, and Chase Davis along with the aforementioned Hjerpe, Saggese, and Roby. From that list, I think Hence and Mathews are the two I have full confidence they would not move for Flaherty, but I'm sure they would strongly prefer not to move the others either.

Third, let's think about how the Cardinals have made some of their creative trades in the past. They once turned Colby Rasmus, a top young player in the game who seemed to have lost his role with the club into Edwin Jackson, Octavio Dotel, Marc Rzepczynski, Corey Patterson, and cash. It seemed like a weird use of the Rasmus asset at the time, but it won them a World Series. The club also recently flipped center fielder Harrison Bader while he was on the injured list for Jordan Montgomery in a deal that seemed to come out of nowhere.

In a similar way, could St. Louis use the valuable asset that is Herrera to hold onto their prized prospects and acquire a rental arm? At the moment, Herrera is down in Triple-A because of how much the Cardinals value what Pedro Pages brings behind the plate. Could they turn his surplus value into a front-end starter?

It feels like an overpay value-wise for Flaherty, but I could see the Cardinals being interested in how it saves them from gutting other areas of their roster and farm system. In 54 games this year, Herrera has been worth 1.0 WAR while posting a .279/.340/.378 slash line, good for a 107 wRC+. He's been a slightly below-average framer while having good blocking behind the plate, and his game-calling has improved as well. Herrera has the potential to be a really good starting catcher for a long time, but his arm strength is the biggest red flag.

With Contreras, Pages, Bernal, Jimmy Crooks III, Sammy Hernandez, and a bunch of catchers just drafted, I could Herrera being the trade chip they dangle. I don't think they'd move him for almost any rental arm outside of Flaherty though.

What do you think of these trades? Are they realistic value for Flaherty? And if so, would you make trade for Flaherty?