SSTN Mailbag: Free Agents, Third Base, Boone's Return, 40-Man, And The Bullpen!

The SSTN Mailbag is back! I know I'm a bit overdue on my promised return to the Mailbag, but it's better late than never. In case you're curious, I have been rooting for the Milwaukee Brewers since the Yankees were eliminated. Why? 2 very basic reasons:

1. I am forever a Gary Sanchez fan. He was always one of my favorites when he played for the Yankees, and I really want to see him win. I also called the ascendency of Jake Bauers (as some of you who have been around here for a while might recall), I was just a bit early, so I'd like to see him win as well.

2. I love the way the Brewers are managed and play the game. It's a smart organization that works really hard to blend analytics, scouting, new biomechanical assessment, and traditional fundamental baseball in a way that I think all organizations should aspire to balance. Contrary to popular belief, I think the Yankees are really good at 3 out of the 4 aspects of running an organization (guess which one they haven't been good at in a long time...), but the Brewers are close to my ideal of how an organization should run. It's fun to watch the way they play baseball.

I'm still sad that the Yankees lost, but I'm still enjoying baseball and will be sad to see it end. At the end of the day, I love the game, and am sad when it's over.

I don't want to take a long time with my intro today; you have all kept peppering the SSTN Mailbag with questions during this abnormally long hiatus, and I want to devote the appropriate amount of time to questions. As always, thanks for the great questions and keep them coming to SSTNReadermail@gmail.com. In this week's SSTN Mailbag, we'll talk about the Yankees' own free agents, third base, Aaron Boone's potential return, the 40-man roster, and the bullpen! Let's get at it:

Brad S. asks: The Yankees have some interesting options this off-season, heightened by the uncertainty of the owner vs. union negotiations.

In a normal year, the discussion would be what to do for 2027. So while we sit on the edge of our seats during the playoffs, I thought it would be fun to consider what off-season actions the team will take.

Starting with decisions on expiring contracts:

Brad lists a host of players, so I'll discuss those players' futures below as Brad listed them:

Jazz Chisholm - I like Jazz more than most, but I thought his focus was lacking and he needs a strong manager to get the most out of him. I don't think the Yankees' current clubhouse is the right environment to get Chisholm to play like the 5-tool superstar I think he's capable of being at his peak (and the one we've seen flashes of in his 2.5 years as a Yankee). I think my previous estimates for his free agency were a bit off, and he looks like he'll be one of the top free agents on the market, even despite his struggles this year. With the Qualifying Offer at $23 million this year, I wouldn't offer it to Jazz, and I'd let him walk in free agency, even with the understanding that it clears the path for a likely inferior player from a pure talent perspective.

Trent Grisham - I don't need to belabor this one for long. Grisham was better than people realize as a Yankee, and he really performed prior to his string of hamstring injuries, but it's time for the Yankees to get younger and faster in the outfield. Grisham should have shifted towards being a useful bench bat for the team, but Boone kept him in absurd spots in the lineup. It's time for the Yankee to wave goodbye to Grisham.

Amed Rosario - Great vibes guy, but he was bad at the one thing he was supposed to do: crush left-handed pitching. It really hurt the Yankees more than people realize that he didn't do his job this year. Bye bye.

David Bednar - Have you looked at what the Yankee bullpen looks like for next year??? It's ugly. I can't believe I'm saying this, but I would offer Bednar the Qualifying Offer, but work to sign him to an extension both beforehand and after to keep him around.

Paul Blackburn - He'll have some offers out there, but he also ran completely out of gas at the end of the year. I'd look to bring him back, but not at any cost.

John Schreiber - A totally replaceable arm, but appeared useful. I think he can be kept around for almost nothing, so sure, why not?!?

Tim Hill - The magic has worn off. Hill is far too hittable, so it's time to say goodbye.

Ryan Yarbrough - Surprisingly, I would keep Yarbrough around. He's a useful swing arm, and while I wouldn't hesitate to cut him if the Yankees can find a better option, he stays healthy and he's able to competently soak up innings. At some point, he's going to lose just enough velocity to have the house of cards collapse, but he remains useful.

Michael Fulmer - I really like Fulmer, but he's the type of pitcher you can give an invite to Spring Training next year to see if he has anything left.

Fuster asks: what's your idea

for next year at third?

AND

Brad S. asks: Ryan McMahon--I think there is more in the tank here just as I believe in Wells. He hit .250 at home this year, and I think he could benefit from working with Judge's off-season trainer. He has been showing some big-moment potential in big moments. Keep him another year with Volpe and Caballero to back him up until Roderick Arias is ready.

I'll tell you what I wouldn't do: let Ryan McMahon anywhere near this roster. I wrote for years about McMahon prior to his acquisition; I noted that I didn't love his chances of being a productive bat, but I understood acquiring a defensive whizz at 3B. Well, now he's not even particularly good defensively at 3B.

I also want to make a note regarding Aaron Judge's personal hitting coach. That approach has worked for Judge, which is great. That coach works with hosts of other big league hitters. Some are decent bats in the big leagues, while his teachings haven't taken at all for others. I personally do not agree with everything Judge's coach preaches as fact regarding the baseball swing, and there's pretty good evidence to suggest that his approach doesn't work for everyone. I'm sure McMahon has worked with multiple coaches to fix his swing over his career. It hasn't worked. I don't think there's a world where McMahon can get to enough contact to make it work if he's not a premium defender, which he isn't anymore.

So no, McMahon is not part of my solution at 3B. As I see it, the Yankees have two options:

1. Find a platoon partner for Volpe at 3B, and that assumes they can find a 2B. Obviously, this isn't likely.

2. Go outside the organization for a 3B.

Option 2 makes the most sense, by a long shot. Unfortunately, the Yankees' options on the free agent market are slim. Edmundo Sosa is a 31 year old career utility man who grades out as an elite defensive 3B who hits the ball all over the field. He also posts among the highest chase rates in baseball and is basically a better, slower version of Jose Caballero.

The big name out there is Teruaki Sato, who will supposedly be posted shortly after the conclusion of the MLB season. He is a very interesting player to watch, and the Yankees are said to have significant interest in his services. Our own Cary Greene wrote about him the other day, and is bullish about his MLB prospects. I have a very nuanced take regarding Sato coming in a few days, but while I think his upside is fantastic, there are very real reasons for concern. The Yankees also haven't been terribly successful in the Japanese market since their signing of Masahiro Tanaka, so I'm not sure how realistic Sato looks this offseason, particularly in light of the looming lockout.

That leaves the trade market. Again, this is a tricky spot, as I'm not sure there's a ton of availability out there right now. It's going to cost the Yankees real prospect capital to grab a real 3B. I think the Yankees can stand to pair a real prospect with some starting pitching depth to acquire a good player this offseason. The real question is whether that makes more sense at 3B, 2B, or in CF.

I lean more towards CF if those are the options. I'm beginning to think the Yankees will bring in someone like Sosa and spend the trade capital in CF.

Steve Q. asks: Do you think the Yankees will bring back Aaron Boone and is there any justification for doing so?

Yes, I do think the Yankees are bringing Aaron Boone back, even if I vehemently disagree with the decision. The only justifications I have for such a decision is as follows:

1. Boone is clearly respected by his players in the clubhouse.

2. He did help guide the Yankees through a turbulent injury season, allowing them to again win 90+ games, as he does consistently.

3. When baseball shuts down on December 1st, a new manager will not get much time to build connections with his players as he would in a normal offseason.

I think there's validity to the 3rd point above, but I think the other 2 arguments lack real merit.

Alan B. asks: GM Andy, do you have any guys you'd non tender? Also, from Yankees own free agents is there anyone(s) you'd push hard to sign before December 1?

I think there are some clear non-tender candidates, but there are also multiple guys leaving the 40-man roster through free agency, which leaves plenty of room to protect 2-4 Rule 5 guys as well. When the Yankees start signing some free agents and making trades, I think the non-tenders will happen pretty organically. Bradley Hanner, Ali Sanchez, Brendan Beck, Yerry De Los Santos, etc. are all replaceable.

As for our own guys, the only one I'd push really hard to retain is David Bednar. He proved he can pitch in high pressure situations in NY, and the Yankee bullpen looks scary right now. I'd make Bednar a priority.

Brian S. asks.: What would you do about the Yankee bullpen? It looks terrifying right now.

It's going to be a tall task to build a bullpen with where the Yankees are starting. I think some trades are in order, but I also believe strongly that the Yankees have some pitching in the upper minors that should be converted to the bullpen this offseason. That's a discussion for another day, as I do have some ideas there.