top of page
  • Writer's pictureAndy Singer

SSTN Mailbag: Robert vs. Bellinger, Gene Michael, and Trade Proposals!

Next week’s Winter Meetings usually mark an exciting crescendo of the off-season. We have already seen a significant signing or two, but the stage appears to be set for another big week. Multiple teams are looking to wheel and deal; we’ll likely find out where Ohtani will land; and it feels like everyone is hunting for pitching. In Yankee rumors alone, we’ve heard a lot about their desire to land prized free agent Yoshinobu Yamamoto, who starred in Japan and figures to land a big long-term deal; that talks with the Padres are serious enough that initial names beyond Juan Soto have been exchanged; and the Yankees have cleared space on the 40-man roster with the clear intention to make some moves. I worry about getting my hopes up too much, and it’s likely that many of this off-season’s moves will happen after the Winter Meetings, but the stage is set for an exciting week.

As always, thanks for the great questions and keep them coming to In this week’s SSTN Mailbag, we’ll compare the merits of acquiring Luis Robert via trade versus spending big money for Cody Bellinger, discuss the legacy of Gene Michael and its relationship to the current Yankees, and evaluate a couple of trade proposals! Let’s get at it:

David asks: Would a trade for two years of right-handed hitting, centerfielder Luis Robert, be a better option than signing left-handed Cody Bellinger to an enormous contract that takes him well into his baseball dotage?

Brian Cashman himself stated that the ideal off-season would include 2 left-handed hitting outfielders finding their way to New York. However, that doesn’t mean that the Yankees should ignore ultra-talented players if they happen to be right-handed. Luis Robert is one of the best all-around centerfielders in the sport. Everyone should inquire about a player as good as Robert, given that the White Sox are likely to rebuild (again).

Let’s start with the bad: Robert doesn’t walk much and he swings and misses far too often, which is a trait too many current Yankees share. However, he’s fantastic in every other way. He punishes the baseball whenever he makes contact, and he makes enough contact to be a consistently above-average (and occasionally great) hitter, with power that plays anywhere; he runs well on the basepaths; and he’s one of the best defensive centerfielders in the sport, combining range with a solid arm.

Bellinger seems to also be an ideal fit for the Yankees on the surface. He’s a former MVP who rebuilt his value after a stunning fall, putting up an excellent year in 2023. He bats left-handed with a swing that appears to be perfect for Yankee Stadium, has experience playing in big markets, and plays good defense in centerfield and at first base. However, the underlying numbers aren’t all that different from recent years when he was unplayable offensively. He’s also about to get a huge contract (I think it will cross the $200 million threshold).

Robert would cost a pretty penny in prospect capital. Think in terms of starting with, say, Dominguez, Peraza, and Pereira and add some pitching on top of it. That’s scary. I’d be more scared of wasting Judge and Cole while they are elite.

I wouldn’t trade Dominguez for anyone but the best. Robert is in that category, and I think he’s a better player than Bellinger. It would hurt, but given ownership’s slavish devotion to the top luxury tax threshold, I’d pass on Bellinger and opt for even a painful trade for Robert.

Reggie proposes the following trade: Giancarlo Stanton to the Angels for Anthony Rendon

Wow, the fact that we even have to think about a trade like this probably makes fans of both clubs want to vomit. These are both ugly contracts, but one is clearly worse. Here’s a fun question: without looking it up, which player has more plate appearances since 2020?




Anthony Rendon has made 857 plate appearances in that time; Giancarlo Stanton has made 1540 plate appearances since 2020, almost double Rendon’s. Not the answer you’d bet on, huh?!? The Angels are on the hook for $38.57 million AAV through 2026 for Anthony Rondon’s services, while the Yankees are on the hook for a comparative bargain for Stanton with a $26.86 million AAV, though that deal goes through 2028 (with the buyout).

Ironically, Rendon probably fits the Yankees’ roster better, were he actually able to play occasionally. The Yankees need a 3B, while they would love to free up the DH slot. However, there’s almost zero chance Rendon would work in NY. Rendon has been notably combative and outright rude to the media in LA, and that would only be magnified in New York. For all of Stanton’s struggles, he handles the media well and the Yankee clubhouse appears very supportive of Stanton. I’m not sure the same can be said of Rondon.

Given those facts, I’d say no if I’m the Yankees, and if the Angels have any hope of retaining a certain DH/P, they probably want to keep that DH spot open…

Alan B. asks: 1. Will the Yankees make a trade next week for a guy on a major league roster?

2. Will Yamamoto sign next week (anywhere)?

3. With 4 open spots on their 40 man roster, will the Yankees actually take someone in the Rule 5 Draft?

4. Over/under: of 3 for stupid or crazy things Cashman will say next week at the Meetings?

1.) Yes

2.) No

3.) I could be wrong, but because the Yankees had a full roster on the day rosters needed to be set to protect guys from the Rule 5 Draft, I don’t believe they get a selection.

4.) Under; he’ll be on good behavior after a couple of weeks ago.

Kendall S. says: Trades, Free Agents, Re-signings, Prospect Development - The only test for any of the above is WWGMD? What would Gene Michael do? The only GM/Executive that in recent history has a proven track record of developing WS Yankee teams. And he started with a lot less than the NYY have now and came forward because the original Boss was out of commission, suspended. Those that forget history do so at their own peril and surprise.

I love the idea of WWGMD being an acronym that just becomes standard lexicon in the Yankee front office. I personally agree wholeheartedly with this approach. Fascinatingly, that alignment is about to lead me somewhere I think many of you will disagree. I consider Kendall’s opinion a very factual accounting of Yankee history from 1990ish to today. With that, I think the following:

1.) I think many Yankee fans would agree that best team builder the team could ask for is a Gene Michael disciple. Who was Gene Michael’s right-hand man throughout the dynasty building that took place during the early 90’s? Brian Cashman. The Yankees already have a Gene Michael disciple in charge of team building. Cashman has talked time and again about how Gene Michael’s mentorship shaped who he is as a General Manager. In addition to his strong ability to scout talent, Michael was known for his ability to stand up to George Steinbrenner, adapting as new information became available, and for remaining resolute in his convictions. Outside of the scouting acumen, Cashman is basically known for the same attributes, though I’d argue that his adaptability has waned a bit in recent years. By those measures, Cashman is still a capable GM.

2.) Yankee ownership has been meddlesome and a hindrance for 35+ years. Despite their significant resources, Yankee ownership has never maintained the balanced rationality required to run a professional sports franchise. George Steinbrenner was impatient, petulant, and meddled in baseball executives’ ability to build a roster. Since 2007/2008 (roughly), Hal Steinbrenner has been largely aloof, exerting no management of the people beneath him while arbitrarily managing budgets based on tax bills as opposed to real bottom-line numbers. The effect is continued meddling in the on-field product. There’s an argument to be made that we really don’t know what Cashman is capable of given the lack of management from the top.

Frankly, I wonder how good Cashman would be with a Steve Cohen-type owner. I know many of you will disagree with me, but I can’t help but wonder.

Oscar proposes the following trade: Carlos Rodon and Everson Pereira to the Arizona Diamondbacks for Ale[k] Thomas.

As many of you will recall, I very much wanted the Yankees to try to pry Alek Thomas from the Diamondbacks for at least the last two years, and possibly longer. I like his skillset, as he brings speed and defense as his core toolset with a bat that has the potential to be above-average from the left side of the plate. To this point, he hasn’t quite put the pieces together during the regular season at the Major League level with any consistency, which gives me pause. However, he also was a star in the NLDS and the NLCS, so the rest of the world got to see what he can do on the national stage.

Realistically, there is almost no chance that the Diamondbacks would make this deal. The fact that the Diamondbacks continue to give Thomas chances tells you how much they like him as a player. I suspect he would have been dealt by now otherwise. Rodon would add a pitcher with ace upside, but also one that has a history of arm troubles and now a back issue. Rodon is owed a lot of money, so for a young team like Arizona, I’m not sure they’d be willing to part with a member of their young core for a pitcher whose performance can be replicated by other current free agents without shedding a good, young player. In a deal like this, Pereira really doesn’t sweeten the pot at all.

I still believe in Thomas, and would love to have him, but this doesn’t get it done; start with someone like Mike King, then the D’Backs might talk.


Dec 01, 2023

can the Yankees afford the prospect cost in order to trade for both of Robert and Soto?

Alan B.
Alan B.
Dec 02, 2023
Replying to

You asked a question, I answered it. To my way of thinking, the only extension that would be talked about, would also have a player's option opt out after 2024, therefore, why talk about it from the Yankees side? That's 2hy I've never looked at this trade except as a one year deal.


Alan B.
Alan B.
Dec 01, 2023

The non-tender date was after the roster was set. Plus the trade of Bauers, leaves the Yankees at 36.

Was Cashman really his #1 AGM? I could be wrong, but the same off season that Bob Watson came to succeed Stick as GM, didn't Brian Sabean go to San Francisco and start creating NYY West? I thought Cashman was more Watson's #1 subordinate than Stick's. Plus Stick has been gone for just over 6 years now (September 2017, if I remember correctly), so even if what you say is true, without Stick around, I believe Cashman has lost his way, and Stick isn't around to make him re-think things.

But I love the WWSD (OK, I'm subbing S for Stick…

Alan B.
Alan B.
Dec 02, 2023
Replying to

Cary, Cary, Cary... Tsk, tsk. Have you forgotten his refusal to fire Dick Howser after the 1980 playoffs?

dr sem.png

Start Spreading the News is the place for some of the very best analysis and insight focusing primarily on the New York Yankees.

(Please note that we are not affiliated with the Yankees and that the news, perspectives, and ideas are entirely our own.)


Have a question for the Weekly Mailbag?

Click below or e-mail:

SSTN is proudly affiliated with Wilson Sporting Goods! Check out our press release here, and support us by using the affiliate links below:

Scattering the Ashes.jpeg

"Scattering The Ashes has all the feels. Paul Russell Semendinger's debut novel taps into every emotion. You'll laugh. You'll cry. You'll reexamine those relationships that give your life meaning." — Don Burke, writer at The New York Post

The Least Among Them.png

"This charming and meticulously researched book will remind you of baseball’s power to change and enrich lives far beyond the diamond."

—Jonathan Eig, New York Times best-selling author of Luckiest Man, Opening Day, and Ali: A Life

From Compton to the Bronx.jpg

"A young man from Compton rises to the highest levels of baseball greatness.

Considered one of the classiest baseball players ever, this is Roy White's story, but it's also the story of a unique period in baseball history when the Yankees fell from grace and regained glory and the country dealt with societal changes in many ways."


We are excited to announce our new sponsorship with FOCO for all officially licensed goods!

FOCO Featured:
carlos rodon bobblehead foco.jpg
bottom of page