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  • Writer's pictureAndy Singer

SSTN Mailbag: Grisham vs. Kiermaier, Monty, And Caleb Durbin!

It has effectively been three weeks since the regular season ended for the Yankees. Enough time has elapsed that I've been able to enjoy watching some playoff baseball, but not nearly enough time to keep me from being further annoyed by the club. In three weeks, we haven't heard a formal peep from anyone in Yankee management. All we have are inside, unnamed sources that speak to certain beat writers claiming that Steinbrenner is wringing his hands, holding stressful internal meetings, and getting ready to unveil his plan for 2024...which should already be in place were this organization run properly from the top. Realistically, the Yankees' season has been over since early August. How does the team not yet have a plan for 2024? Knowing that fans are angry, how tone deaf does Hal Steinbrenner need to be? We haven't even gotten a small platitude-filled press conference, the least the fans deserve. Oh, and the not-audit, but we swear it's an audit event? It won't commence until after the World Series concludes...but by then, it will be close to Thanksgiving, so maybe the guys will need a break...then there's the December holidays and the New know what, just scratch it.

Everything about ownership's inaction proves the point I've been making for years: it is nearly impossible to fairly judge key members of the baseball operations staff, namely Cashman and Boone, when the leadership at the top is so disconnected, yet involved. It would be one thing to be merely aloof; it's another entirely to be in the way, and that's Hal Steinbrenner's legacy until proven otherwise.

The reality is that while there are significant holes in the roster as currently designed, there is a path towards turning it around reasonably quickly; I just think ownership will be too in-the-way to make it happen. I really hope I'm wrong.

As always, thanks for the great questions and keep them coming to In this week's SSTN Mailbag, we'll compare one of my trade targets from last week's Mailbag, Trent Grisham, to free agent centerfielder Kevin Kiermaier; evaluate Monty's fit for the Yankees; and dig into Caleb Durbin's prospect profile! Let's get at it:

Fuster asks: how would you rate Grisham in comparison to Kiermaier?

I knew someone would ask me to compare Grisham to other options after last week's SSTN Mailbag, and Fuster obliged almost immediately. Before I go any further, I just want to note something very clearly, adjacent to this topic: I do not believe that Estevan Florial is even a stop-gap option in CF next year. I know that many praised his performance at the end of the season (basically because he didn't fall flat on his face, given the Yankees' treatment of Florial the last couple of seasons), but I didn't see it at all. He is a classic quad-A player: plenty of raw tools that are exciting at AAA, but it doesn't translate at all to the big leagues. His pitch recognition has not improved since the low minors, and while he made a couple of plays in CF, his routes were horrible, and I'd bet that over time, his defensive value would be average to slightly below over a larger sample size. Outside of a possible power surge, of which he's capable in small bursts, I very much doubt that Florial can be even a .650 OPS guy with average or worse defense in CF. That's not even a stop-gap. I hope he proves me wrong, but that's what I see out there. Given that fact, I strongly believe the Yankees need to go outside the organization for CF help this off-season.

Let's start with a blind comparison, shall we? Below are statistics for two players between 2019 and 2023:

Player A: 1658 PA, .243/.305/.394, .699 OPS, 7.4% BB%, 23.6% K%, .151 ISO

Player B: 2041 PA, .216/.316/.383, .699 OPS, 11.6% BB%, 26.2% K%, .167 ISO

Let's assume that both players are of similar value defensively and on the basepaths. If we equalize those factors, these players are remarkably similar statistically since 2019. Player A makes more contact, though his walk and strikeout rates are out of balance. Player B isn't making an ideal amount of contact, but he pairs that with pop and good enough walk rates to actually post a higher OBP than Player A. If Player A batted .265, this would be a different conversation, but given the other factors that pad Player B's likely performance floor, I'd take Player B as my stop-gap CF and eventual 4th outfielder. So: who's who?




Player A is Kevin Kiermaier. Player B is Trent Grisham. Their relative merits separate more when you dig deeper. Kiermaier has missed a lot of time to injuries in recent seasons, and just played his age-33 season. This is Kiermaier's first full-ish season since 2019, and his offensive peripherals are troubling. It feels like 2023 was Kiermaier's late-career peak, and I worry about his value if his skills blunt even a little bit. I think he'll also prove to be more expensive than he's worth, and given the fact that the Yankees will certainly be looking at the last luxury tax tier as a ceiling as opposed to a cushion to toss aside, I don't think Kiermaier is the best path forward.

Grisham will likely cost prospect capital, but he's also one of the few centerfielders in baseball who has been Kiermaier's equal defensively. While Grisham's batting average has suffered the last couple of seasons, his batting average was much more Kiermaier-eque in his first 3 seasons, and there are positive signs in his underlying profile: Grisham swings and misses too much, but his chase rate was one of the best in the Majors in 2023, and I count 6-7 fly balls that would have been homers in Yankee Stadium in 2023. Add in the fact that Grisham is entering his prime, and he's the guy you go after to be part of a younger core. I don't think Grisham will be terribly expensive in terms of prospect capital, and I think his profile is one that can be successful in Yankee Stadium.

Yankeerudy asks: What are your thoughts on pursuing Montgomery as a free agent?

I know many will consider me a hypocrite, but yes, I'm all-in on going after Monty as my second-best free agent prize after Yammamoto. In fact, I'd rather have Monty than Snell, given that Snell's walk rate is terrifying, and I'm not sure I buy that he'll stay healthy long-term given that this is the first season he's ever thrown 180 innings.

I will reiterate something that I think got lost in the shuffle of my support for the Bader-Monty trade: I have been the high-man on Jordan Montgomery since prior to his initial 2017 call-up. I was the same guy who both wrote at SSTN and discussed on the Bronx Beat Podcast that Monty's post-TJS velocity gains would take him from being a solid back-end starter to a championship caliber mid-rotation arm, which is exactly what happened. Jordan Montgomery was an excellent mid-rotation starter for the Yankees, and though I still am in the shrinking minority that agrees with the the thought process behind the trade for Bader, I'd welcome Monty back with open arms.

One of the biggest misconceptions with Monty is that he has somehow unlocked something new in his performance since he left the Yankees. This is largely false. In fact, the version of Monty that has dominated in the playoffs is basically the version of Monty the Yankees created last season: a guy who mixed his sinker and four-seamer north and south while using change-ups and curves to vary his arsenal against lefties and righties. Monty can attack lineups with multiple looks, given his ability to command multiple fastballs, his curve, and his change-up like a classic soft-tossing lefty, except Monty throws 94 MPH now. He's also proven to be a guy that can take the ball every 5th day since he fully recovered from TJS.

Sign me up; I'd pay $25-30 million per year for that type of pitcher. And I don't buy that he wouldn't sign with the Yankees again; he was hurt by the trade, as all players are when they leave the team that developed them. It's a business, he's familiar with the organization and the clubhouse dynamic (which he was said to be a positive part of), and he's more marketable in NY than elsewhere. I'd make a reunion happen in a heartbeat.

Alan B. asks: With how Caleb Durbin played this year, as more of a throwback middle infielder leadoff hitter, and [now] in the AFL & scheduled to be in AAA in '24, do you see him factoring in or even changing the thought process of what the Yankees want to do at 2B or SS going forward? Oh, and he's not Rule 5 eligible till after next year (like another 10 or so prospects)

A quick note about statistics in the Arizona Fall League this season: take them with a grain of salt. Multiple scouting outlets have reported that the quality of pitching is the lowest it's been in recent memory. Fringe hitters are feasting on fringe pitching that both doesn't have big league stuff and can't command it in the strike zone (again, this is a generalization). I'm excited that Durbin is hitting in the AFL, but I'm also not putting any stock in the numbers themselves.

What I am putting stock in is the player. I did a quick write-up on Durbin after the Luetge trade, and at that time, the tools weren't squaring up with the performance. The Yankees re-tooled Durbin's swing to plant on his back leg a bit more, and that has allowed Durbin to make more consistently strong contact and find the gaps. Unlike most Yankee prospects though, Durbin has combined this with elite plate discipline, walking more than he strikes out while striking out at among the lowest rates in the minors. He's 5'6" (maybe 5'7"), 175-185 lbs, and he can flat out run, with good hands in the infield. He's a bit old for the levels he's played at, but I think he's put himself on the fringes of the Yankees' top-20 prospects.

That doesn't mean that he's changed the Yankees' plans yet. I think Durbin might be a very interesting prospect to watch this year, but he has to do it again at AA/AAA to announce that his contact/speed profile is for real. I also have real questions that his arm will play anywhere other than 2B, and I'm not sure he has enough power to be anything more than a utility guy, but he's proven people wrong at every stop. I like Durbin quite a bit, and look forward to seeing what he does against upper level pitching this year.


Alan B.
Alan B.
Oct 20, 2023

While I don't know what kind of player Florial will be, I do believe he is the best option to be a stopgap/placeholder until Dominguez is ready. (Now, if the Yankees were to sign Bellinger, I'd let Florial and Pereira battle it out.) My issue with bringing anyone in, will cost money. While the money in the big scheme is not necessarily a big deal, it ends up determining who plays, and who doesn't play. Neil Walker in 2018, and IKF in 2022 both prove my point. Bird got hurt again in Spring Training, so Tyler Austin ended up being the OD 1B. He got off to a great start, then because of the fight with the Red Sox…


Oct 20, 2023

keeping in mind that neither Kiermaier nor Grisham are more than a stop-gap starter and better suited to back-up duty, what would you consider a reasonable salary offer for Kiermaier

or a reasonable trade offer for Grisham?

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