Answering 20 trade deadline questions on the Yankees, Phillies and other expected contenders (2024)

As baseball heads into the Memorial Day weekend, traditionally a point in the calendar for taking stock, we asked subscribers to submit early trade deadline questions about their favorite teams. Earlier in the week, I looked at the expected sellers and the players they could dangle. Today, we’ll focus mostly on the top contenders — their needs, how they will approach trade season, and my takes on your trade proposals for them. Check back Friday for a second installment of the mailbag that will hit on a bunch of other teams.

Questions have been edited for clarity and length. Thank you to everyone who asked them.

1. What holes should the Yankees aim to address at the trade deadline? — Andrew B.

The Yankees don’t have any glaring needs but more bullpen depth is always needed, especially in the last two months of the season. I also think they should keep an open mind on the infield corners if a star becomes available who fits either as a rental or even long term. First baseman Anthony Rizzo and third baseman DJ LeMahieu will finish this season at 35 years old and both are high risks for injury and decline this year and beyond.

2. The Yankees like grabbing relievers who are underperforming and undervalued with their current team and turning them into quality bullpen arms, like Clay Holmes. Who is someone the Yanks should target who could help their bullpen down the stretch? — Zach P.

There are several under-the-radar relievers the Yankees could target from non-contending teams including Nationals righties Derek Law (2.76 ERA) and Dylan Floro (0.38 ERA) and Cardinals lefty JoJo Romero (1.42 ERA). But my two favorite targets for them are A’s righties Austin Adams and Lucas Erceg, who have been stellar in set-up roles for closer Mason Miller.

3. Does it make sense for the Yankees to seriously consider making a deal for Paul Goldschmidt? I personally like Rizzo and don’t feel that first base is a position of need. What are your thoughts? — Neil V.

I think it depends on how Goldschmidt performs between now and the trade deadline. If he shows over the next couple of months that he would be an upgrade over Rizzo or an upgrade in a platoon with him, then I would consider it. He’s still a plus defender at first base, a leader in the clubhouse and a flat-out winner. I wouldn’t overpay for Goldschmidt, who will turn 37 in September, considering he’s a rental and has the same age and decline issues as Rizzo. However, to deepen the lineup and protect against future injuries, it makes some sense.

4. Is Mason Miller a realistic trade possibility for the Phillies? Do you think they could land Miller with a prospect package of outfielder Justin Crawford and starting pitcher Mick Abel plus maybe a lower-end prospect and a current role player? — Owen S.

If I’m the A’s, I am converting Miller to the starting rotation where I believe he can develop into a No. 1 type of starter. If they’re not going to make him a starter, they should deal him now, when they would get the best possible return. So what’s a fair package for Miller from the Phillies? From Oakland’s side, I’m asking for third baseman Aidan Miller, who is ranked as the Phillies’ top position player prospect by MLB Pipeline, and Mick Abel as the return, or Miller and starting pitcher Andrew Painter, their top overall prospect, if I’m comfortable with how his rehab is progressing after Tommy John surgery last year. Those are steep asks, but Miller is that good, on and off the field.

5. Is there a creative way the Phillies could trade Nick Castellanos without throwing in a high prospect or retaining salary and (still) get a more consistent player at the plate along with a better glove in right field but perhaps someone with less upside than Castellanos (if he gets hot this year)? — Fletch F.

Castellanos makes $20 million per year through the 2026 season and is not tradable at that price point without paying at least 50 percent to 70 percent of his remaining salary. However, at age 32, he should be able to perform much better in the second half and still end up with 20 home runs and 70 RBIs by the end of the season. But I would prepare for him to finish his career as a Phillie.

6. The Orioles look like a team that is poised for a deep playoff run, with the exception being the bullpen. Personally, I think the O’s are at least two arms short. Who matches up well with them? — Keith R.

I think the Orioles need an impact closer like Mason Miller or Ryan Helsley of the Cardinals. They could use two more set-up relievers as well. In terms of who matches up well with them, the answer is all of the 29 other teams. That’s because the Orioles possess one of the best and deepest farm systems in baseball and have enough organizational depth to trade multiple outfielders, infielders and pitchers in their farm system. However, it’s important for general manager Mike Elias to continue to not include any of their top prospects — such as Jackson Holliday, Samuel Basallo, Coby Mayo and Enrique Bradfield Jr. — in trades, like he was able to do in the swap for Corbin Burnes. The Orioles’ system is so loaded, Elias could dangle talented-but-lesser prospects — like Connor Norby, Dylan Beavers, Jud Fabian and Braylin Tavera — to accomplish their goals.

7. Assuming the Orioles are buyers, which of their top prospects would seem redundant to their depth at the MLB level and thus be looked at as legitimate trade candidates? — Christian L.

I think the best trade bait for Elias at the end of the day will be outfielder Heston Kjerstad and one of their top pitching prospects — either righty Chayce McDermott or lefty Cade Povich. A package combination that included two of those players should be able to land Baltimore an impact closer and a legitimate set-up reliever or two. Again, if I’m the Orioles, I would prefer to deal from the prospect pool I listed in the above question, but if push comes to shove they have enough depth to trade Kjerstad and McDermott or Povich.

8. Does Erick Fedde make sense for the Orioles? Would a White Sox-Orioles swap of Fedde for Connor Norby make sense for both teams? Baltimore gets a controllable starting pitcher on a team-friendly contract and the White Sox add a promising prospect to their second base/left field mix. — Greg D.

This trade idea makes sense for both sides, but let’s expand the deal and try to acquire one of the White Sox relievers as well, either righty Steven Wilson or lefty Tim Hill, or for that matter, let’s go bigger and propose a deal for Fedde, Michael Kopech and Steven Wilson for a prospect package of Dylan Beavers, Jud Fabian and Norby. Fedde improves the Orioles’ rotation, Kopech can share the closer role with Craig Kimbrel and Wilson adds another quality arm to the bullpen.

9. What do you think of these Dodgers trade scenarios:

Blue Jays SS Bo Bichette to L.A. for 2B Gavin Lux, C Dalton Rushing, RHP River Ryan and RHP Payton Martin

OR

Marlins LHP Tanner Scott to L.A. for C Diego Cartaya, OF Jose Ramos and RHP Kyle Hurt — Andrew C.

I love the idea of the Dodgers trying to land Bichette from Toronto as long as they talk with Mookie Betts first and make sure he’s OK with moving to second base full-time, which knowing him shouldn’t be a problem. However, if I’m the Blue Jays, to part with Bichette, I’d need right-handed starter Gavin Stone as the headliner, along with Lux and Rushing to make the deal work.

In terms of Scott for Cartaya, Ramos and Hurt, I think that’s an overpay for Scott if Cartaya ends up hitting, but I’d have to at least consider the deal since Will Smith is signed long term and Cartaya is never going to be the Dodgers’ long-term catcher. Scott will be a free agent after this season.

10. As beloved as Chris Taylor is for his track record, community work and clubhouse presence, are the Dodgers looking to trade him and what could they potentially get for him? — Tae K.

Taylor is done. He hit .221 in 2022, .237 last year and is batting .097 this year at age 33. He’s just 6-for-62. He has zero trade value. The Dodgers’ only option to move on from Taylor is to release him. However, he’s signed for $13 million next year and they will owe him a $4 million buyout for 2026. At some point, whether it’s this year or next, they’ll have to eat the rest of his contract.

11. For an underperforming but loaded roster, in what spots do the Braves try to improve without mixing things up too much? — Matthew P. … What are the chances the Braves shake something up with their core starting nine should they continue to underperform? — Josh R.

The Braves’ biggest need is another starting pitcher. Losing Spencer Strider to season-ending elbow surgery created a huge hole. They also could use one more reliever. In terms of position players, they’re good enough to win the World Series as is. There’s no chance they shake up their core starting nine, nor should they.

12. Other than Zach Eflin, what are some realistic starting pitcher trade options for the Braves to pursue? — Justin F.

Jesús Luzardo of the Marlins, Erick Fedde of the White Sox, JP Sears of the A’s, Tyler Anderson and Patrick Sandoval of the Angels, Jack Flaherty of the Tigers, Chris Bassitt of the Blue Jays and Luis Severino of the Mets.

13. Guardians biggest trade target(s)? — Tyler R.

Heston Kjerstad of the Orioles, Taylor Ward of the Angels, Max Kepler of the Twins and Bryan De La Cruz of the Marlins.

14. What would you say is the single biggest need among the expected contenders? — Blane R.

I’ll run through nine of the top teams, including some I’ve discussed above.

Yankees — bullpen depth
Orioles — a closer and bullpen depth
Dodgers — bullpen depth
Phillies — bullpen depth
Braves — a starting pitcher
Mariners — another power bat
Guardians — another power bat
Rangers — starting pitching and bullpen depth
Brewers — a middle-of-the-rotation type starter

15. Which teams could fade and become sellers and, if that transpires, whom could they make available? — Nick P.

The Blue Jays will fade, with Bo Bichette, Vladimir Guerrero Jr., Chris Bassitt and Jordan Romano possibly becoming available. The Mets could make Pete Alonso, Starling Marte and Luis Severino available. The Cardinals could make Ryan Helsley, Paul Goldschmidt, Lance Lynn, Kyle Gibson and Nolan Arenado available. The Tigers could make Jack Flaherty available.

16. All the talk for the Astros is centered around selling, but what would buying look like for them? I think owner Jim Crane is more likely to double down than fold. — Donald C.

I think the Astros will make the playoffs as a division winner or wild-card club and never doubted them despite their poor start to the season. Adding bullpen depth should be the top priority as well as starting pitching depth, due to the down year from Hunter Brown and the ineffectiveness of Spencer Arrighetti and J.P. France, which played a big role in their slow start. In particular, they could use another left-handed reliever for the fifth, sixth or seventh innings.

17. Hey, JB. As a Cubs fan, I realize they are probably one year away from being serious World Series contenders. But if they want to take advantage of a mediocre NL Central this year, they need bullpen help. Their system is loaded with outfield prospects. Are Owen Caissie and Kevin Alcántara enough to entice Oakland for Mason Miller? … Love listening to you and (Jim Duquette) on Sundays. — Phil B.

Thanks for the kind words, Phil. I appreciate them. The Cubs have a legitimate chance of making the playoffs as either the division winner or one of the wild-card teams. They also have a chance of being a surprise postseason success story thanks to the top of their rotation with Shota Imanaga, Justin Steele and Javier Assad. Those three are capable of running the table in October. Therefore, I think the Cubs need to spend a lot of time between now and the trade deadline trying to find ways to improve the bullpen and add another impact bat to the lineup.

That said, I would not trade Caissie because I think he’ll develop into that middle-of-the-order impact bat by sometime next year. I’m also a fan of Alcántara even though he’s struggling at Double A to start the year. (Remember: He’s only 21 years old.) I would hang on to both. Again, I don’t think the A’s are going to trade Miller because he has a chance to become a No. 1 starter if they develop him working toward that goal. If I’m the Cubs, I’d focus on targeting relievers such as Kyle Finnegan of the Nationals and Jason Foley of the Tigers who will come at a much lower price than Caissie and Alcántara.

18. Who are the Cubs’ untouchables? I would think Cade Horton and Matt Shaw, but I would hope Pete Crow-Armstrong and Caissie too. I could see them dealing Alcántara and Alexander Canario. — George R.

I really like the way the Cubs are rebuilding and agree they should hold on to Horton, Shaw, Crow-Armstrong and Caissie as well as Canario and Alcántara. I’d rather see them use the depth of their farm system to make trades, like the Padres and Orioles have been doing lately.

19. Will the Rays blow things up if they continue to hover around .500? They have a wealth of position players in the minors who could get a look, and Zach Eflin, Brandon Lowe, Randy Arozarena and Yandy Díaz aren’t getting any cheaper. This reminds me a little of the reset they did in 2018, trading Chris Archer even though they were within range of a playoff spot. — Daryl B.

The Rays are not going to “blow things up,” but just like they did with Tyler Glasnow last offseason, they will evaluate players on their roster they control for only two more years and consider moving them this winter. I can’t see them “selling” at this year’s deadline either. They’re good enough to stay in the race for the final AL wild-card berth and I could see them adding a bat at the deadline.

20. Who is the biggest blocked prospect who could conceivably be dealt at the deadline? — Jeff C.

That’s a great question, but in this day and age, teams don’t normally trade prospects who are blocked; instead, they typically just change the position of the prospect or the major-league player who is blocking them. For example, the Orioles moved Jackson Holliday to second base with Gunnar Henderson at shortstop and the Rays recently moved Junior Caminero to play some second base in the minors since Isaac Paredes is blocking him at third base. Another fairly recent example: The Royals took catcher MJ Melendez and moved him to left field because Salvador Perez was blocking him behind the plate. In 2024, teams emphasize positional versatility to overcome the “blocked” issues that clubs dealt with differently 10 years ago.

(Top photo of Mason Miller: G Fiume / Getty Images)