SSTN Mailbag: Grisham And Trade Proposals!

The offseason has officially begun! The World Series was fantastic, right up to the very end. It didn't go the Yankees' way (again) this season, but as a baseball fan, I think that this was one of the best World Series I've seen in quite some time. Both the Dodgers and the Blue Jays played good, hard baseball, and it was very evenly matched over 7 games. I'm very satisfied as a baseball fan, but now I'll spend the next couple of months missing baseball.

I've got a slightly shorter Mailbag this week, as I've been busy away from SSTN and I've been doing a ton of writing. Over the next couple of weeks, you'll see two separate offseason plans from me: one for if the Yankees decided to turn on the lights and fully operate the Death Star, and one that looks a lot closer to the pragmatic approach the Yankees have taken over the last decade. I also have a bunch of scouting reports and other posts of interest, so I'll be around a lot more this month and next, so keep an eye out.

As always, thanks for the great questions and keep them coming to SSTNReadermail@gmail.com. In this week's SSTN Mailbag, we'll evaluate Trent Grisham's case for receiving the qualifying offer and evaluate a couple of trade proposals! Let's get at it:

Steven G. asks: I think Trent Grisham might have the most interesting QO case in baseball this off-season. If you were the Yankees, would you offer Grisham the QO and would you be upset if he took it?

Well, we now know that the Yankees offered Grisham the qualifying offer. MLB altered the qualifying offer structure a number of years ago, which was greatly needed. Previously, in addition to the monetary offer, teams that signed free agent players with a qualifying offer attached were forced to give a first round pick back to the team that offered the qualifying offer. That massively depressed the free agent market, so MLB relented and kicked it back to a pick after the fourth round for teams that pay luxury tax, Competitive Balance Round A or B for teams accepting revenue sharing, and Competitive Balance Round B for all other teams.

The Yankees wouldn't get a ton back for Grisham in the event that he goes out into the market for a long-term deal, but the team has had success with mid-round draft picks in recent years, particularly on the pitching front (see Schlittler, Cam). At worst, the Yankees pay Grisham's QO of $22+ million for 2026. In this case, I agree with the Yankees.

Grisham's 2025 season looks like an outlier when you compare it to his recent seasons, however there were also very real mechanical changes that helped Grisham produce at a near-All-Star level this past season. He's lost multiple steps in the outfield in recent seasons, but he remains solid in CF save for a multi-week defensive slump around a pulled hamstring that tanked his defensive numbers. Grisham, if nothing else, is incredibly patient at the plate and offers a solid performance floor. He also protects against the possibility that the Yankees are left without one of Bellinger or Tucker in the free agent market. If Grisham is even 80% of what he was last season, the salary isn't exorbitant relative to the market.

I agree with the Yankees' decision to offer him a qualifying offer, but I do think that Grisham will get a solid multi-year offer elsewhere.

Nolan P. offers the following trade proposal: Ryan McMahon to the Diamondbacks for Alek Thomas. 

Alek Thomas was a prospect in whom I had significant interest. The Diamondbacks have now given him multiple years to develop at the big league level, and his bat just hasn't translated despite some interesting underlying numbers. Pitch recognition remains a problem and Thomas has not fixed his propensity to chase breaking and off-speed stuff out of the zone. Thomas is athletic and a good defensive outfielder, but the Yankees can do far better in the outfield. I'd pass on Thomas.

Reggie offers the following trade proposal: Luis Gil to the Cards for [Brendan] Donovan.

Here, I am far more interested. As I work through a variety of offseason plans, Donovan's name keeps looking realistic as I try to assemble a team, and he'd fit in nicely with this Yankee roster. Donovan slaps the ball all over the field with high contact rates, but he also has a tendency to pull fly balls. Donovan's current home park takes away some homers to RF, but at Yankee Stadium, he'd likely see a power boost on balls that are outs and doubles elsewhere. I like Donovan quite a bit at 2B or in the outfield for the Yankees.

Starting pitching would absolutely be a basis for any trade with the Cardinals. I think any trade with them starts with one of Gil or Will Warren. Add a mid-level prospect, and I think you have an interesting basis for a deal. Reggie's head was working in a very similar direction to my own here.