Now that the deadline has passed, we can see more clearly that some teams didn't fill all their needs. In particular, the Cubs and Red Sox both needed a top-of-the-rotation starter, and didn't get one. Both are being criticized now for being too value-conscious, and/or too difficult to negotiate with. So let's play some woulda coulda shoulda, and see what might have been.

 

The Cubs

It’s tough to envision the Cubs going deep into the playoffs with a rotation of Matthew Boyd, Colin Rea, Mike Soroka, Shota Imanaga, and Cade Horton. Granted, there was no proven ace on the market. But there were top arms available – for the right price. Problem was, the Cubs just couldn’t bring themselves to pay the asking price.

Why not? They’ve only got Kyle Tucker for this year. Unless they extend him (and there’s no indication that will happen), the time for a ring is now.

So let’s see what might have happened if they had ponied up for a top starter. Let’s assume for this exercise that all trades were either fair or a slight overpay to win the bid.

 

Acquisition target: Joe Ryan

Deadline surplus value: 68.3

Cost: Multiple top prospects

 

 

In theory, a plausible Joe Ryan deal would likely have cost them four prospects: SS Jefferson Rojas, OF Owen Caissie, pitcher Jaxon Wiggins, and OF Kevin Alcantara, plus young starter Ben Brown. That's a haul.

Presumably, the Cubs didn’t want to decimate their farm system with this type of deal. But even in this scenario, they could have kept top catching prospect Moises Ballesteros (who was reportedly off limits), plus young 3B Matt Shaw, and guys like Jonathan Long and Brandon Birdsell. And keep in mind, they’d have Ryan for two more years after this one – three chances to go deep into the playoffs. The farm can always be replenished with other trades, draft picks, or international signings (just ask A.J. Preller). 

 

Acquisition target: Mackenzie Gore

Deadline surplus value: 65.1

Cost: Multiple top prospects

 

 

The price for Gore was similar to the price for Ryan, so the packages proposed would have likely contained the same types of prospects.

 

Alternative option:

Acquisition target: Sandy Alcantara

Deadline surplus value: 13.7

Cost: Multiple prospects

 

Alcantara would not have cost as much in prospect capital, because the Cubs would have been taking on more money (the remainder of his $17M salary this year, and another $17M next year, plus a team option for $21M in 2027). It’s also less certain that Alcantara will fully return to his former top form, as he’s had a very up and down year.

A trade for Alcantara didn’t actually happen because the gap between what the Marlins were asking for and what buyers would pay for him was too large. But just for fun, let’s pretend they met somewhat in the middle – the Cubs agreeing to an overpay and the Marlins lowering their lofty price, a little:

 

 

This type of deal wouldn’t have made as much of a dent in the Cubs’ farm system. Miami would get one consensus top prospect in Rojas, a flyer on 1B Jonathan Long, and some further upside with pitcher Jordan Wicks (himself a former top prospect). This one would have benefited everybody.

 

The Red Sox

Reports are emerging that the Sox tried to get a top pitcher as well (Joe Ryan’s name came up here too) to pair with Garrett Crochet in a playoff run. We’ve also heard that Sox President of Baseball Operations Craig Breslow was very value-conscious, so was reluctant to part with too much young talent to get a deal done. But what if he did?

 

Acquisition target: Joe Ryan

Deadline surplus value: 68.3

Cost: Multiple top prospects

 

 

This deal would have cost them SS Franklin Arias and pitchers Payton Tolle, Brandon Clarke, and Connelly Early. Yes, it wold have put a dent in the Sox farm, no question. But it also assumes young talent like Roman Anthony, Marcelo Mayer and Kristian Campbell were untouchable. You can’t keep everybody, right? And given the Twins’ strategy to go into full rebuild mode, they would not have wanted a player whose MLB clock had already started (like Jarren Duran or Wilyer Abreu). They would have wanted prospects.

Would the Sox have been okay losing Arias, Tolle, Clarke and Early? Probably. They can always replace them later in the draft, the international market, or with free agents. And having Ryan as a #2 to Crochet would have been a scary combo for the next three postseasons.

You could play a similar game with a Mackenzie Gore package. Or, Breslow could have pivoted, and given up a bit less, like this:

 

Acquisition target: Sandy Alcantara

Deadline surplus value: 13.7

Cost: Prospects

 

 

In this one, the Marlins would get two prospects with some helium (Tolle and OF Harold Rivas), who would fit their window better, and the Red Sox would have had Alcantara for at least two (and probably three, if the option is exercised) playoff runs to come. Yes, they would have overpaid and taken some risk that Alcantara never fully recovers his form, but this seems like a reasonable price to pay for that gamble.

 

So...

Should these deals have been done? I think so. They would would have benefited all parties involved. But there's woulda coulda shoulda, and there's reality.