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Oliver James Montgomery-MLB trade deadline: Six deals that make sense for contenders
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Date:2025-04-09 00:00:07
The Oliver James Montgomeryfirst rule of Major League Baseball’s trade deadline is that it’s never quite as close as it seems. Sure, we’re just four days away from the July 30 6 p.m. ET buzzer, but a slow and uninspiring market means we are once again urging you to touch grass for most of that time.
Or you could engage in well-reasoned hypotheticals that run the risk of sowing false hope. We’re glad we can help.
Matching tradeable player and contending team at the trade deadline is like playing full-contact Jenga in a tornado, especially with inventory this tight. That said, let’s break down six marriages waiting to happen among trade candidates and contenders as the market perks up:
Red Sox: Right-handed hitter
The surprise AL wild card possessors really need bullpen help, but so does almost everyone else, and first-year GM Craig Breslow has indicated on multiple occasions a righty bat is a priority. Foolish as it is this time of year, we’ll take him at his word.
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You can see the logic: Tyler O’Neill is once again going off – with 20 home runs, and on a 10-for-23, four-homer binge in five games since the All-Star break – but could use another righty stick to balance the lineup. Import another bat and Boston could be an impossible late-inning matchup with a three-batter minimum rule: Jarren Duran (L), New Guy (R), Rafael Devers (L), O’Neill (R), Masataka Yoshida (L).
The Red Sox farm system is middle-of-the-pack and lacks the pitching prospects selling teams covet. But that makes them not unlike virtually every contender, and years of non-contention means the pantry is full enough to win the bidding for a power bat just entering his arbitration years.
The match: Brent Rooker, Athletics.
Orioles: Starting pitcher
Right now, the Orioles embody the “life comes at you fast” narrative. Not only did their rebuild get done faster than a post-World War II prefab home, but the peak of their window might be right this second.
Oh, GM Mike Elias’s idea is to pry it open for a decade, and his conveyor belt of elite hitters is making that look like reality. But with rental ace Corbin Burnes pitching to expectations and Grayson Rodriguez healthy and more than worthy the No. 2 slot, Baltimore might not align like this for a while.
So, who starts a Game 3 in the ALDS, the ALCS, the World Series?
With three starters lost to season-ending injury, they’d rather it not be back-end types like Dean Kremer and Albert Suarez, and here comes the answer to a question we’ve all wondered: How deep does Elias go into his prospect trough to reel in an ace?
There’s so many routes to go. A reunion with Jack Flaherty – not at his best a year ago but throwing the ball well for Detroit – isn’t out of the realm. The club could afford to take on Jameson Taillon’s salary – the Cubs would probably help a bit – with Burnes’ and closer Craig Kimbrel’s contracts expiring.
But Elias can live for both today and tomorrow, not just adding a shutdown arm – albeit with innings limit concerns – but also an elite lefty with two years of control remaining to pair with his fleet of bats.
The match: LHP Garrett Crochet, White Sox.
Yankees: Reliever
The never-ending funk – 23 losses in 34 games – rumbles on, and with it a nauseous feeling that the Yankees, still not out of the AL East race, need upgrades just about everywhere.
Old pal Luis Severino might have been right that the lineup has just two hitters to worry about. Nestor Cortes has hit the wall. Carlos Rodon is inconsistent. Clarke Schmidt is still out. Marcus Stroman has struggled in recent Septembers.
So, let’s shore up the bullpen.
Sure, GM Brian Cashman could be moved to dig deeper into his prospect bag and move a Spencer Jones or similar prize for a frontline starting pitcher. An infield bat is paramount. But even though the Yankees’ quietly potent farm system – a consensus top 10 to 15 group – can win some trades, they may lack the highest-end quality for marquee additions.
With that in mind, we’ll let the Yankees surprise us with a power move while projecting something less volcanic. Another All-Star closer with putaway stuff who can alleviate the burden on Clay Holmes, who has had an uneven five weeks, as necessary.
The match: RHP Kyle Finnegan, Nationals
Guardians: Starting pitcher
It’s been a minute since the Guardians were so obviously buyers, and it would behoove them to inspect their not-so-distant past when approaching this deadline. On July 31, 2016, they sent four prospects – Clint Frazier, J.P. Feyereisen, Justus Sheffield and Ben Heller – to the Yankees.
In return: Andrew Miller, who put on one of the greatest postseason relief performances in baseball history, taking Cleveland to Game 7 of the World Series. And none of the four relatively vaunted prospects they gave up for Miller didn’t exactly come back to haunt them.
This time, Cleveland is in relatively dire need of a starting pitcher. Gavin Williams has not been crisp in his return from injury, and Carlos Carrasco has been asked to do far too much .
Know thyself, above all, especially at the trade deadline. The Guardians don’t have a deep farm system but it got replenished by the largest bonus pool available in this month’s draft. It would be uncharacteristic for Cleveland to unload the prospect pool on a guy like Crochet, and unlikely that they’d take on the $36 million due Taillon the following two seasons.
Instead, they can pay the lighter premium for a bounceback guy from a division foe that’s years away from worrying about helping out a rival.
The match: Erick Fedde, Chicago White Sox
Dodgers: Infielder or outfielder
Andrew Friedman’s glory days of peak “optionality” are over. The ability to move players all around the field and platoon like mad have been limited by age and performance, as Chris Taylor (33, .167 average, .542 OPS) and Kiké Hernández (33 next month, .193, .567) aren’t what they used to be. Third baseman Max Muncy is still on his way back from an oblique injury suffered more than two months ago.
Mookie Betts isn’t quite back from a broken hand. Miguel Rojas is on the IL. Andy Pages and James Outman are uncertain options in center. Why not bring in a guy with the kind of speed, versatility and contact ability that plays well in the postseason?
The match: Nico Hoerner, Cubs
Padres: Starting pitcher
Yep, things are really starting to gel in San Diego. Offseason acquisitions Michael King and Dylan Cease give the club a solid 1-2 punch, even before Cease went and no-hit the Nationals. The lineup is punishing one through six.
And while they could use another reliever, closer Robert Suarez has locked it down, saving 23 of 25 games, a percentage better than even franchise stalwart Trevor Hoffman.
Yet with Yu Darvish on the restricted list and Joe Musgrove’s return iffy given the specter of elbow inflammation, the Padres could stand to get another guy who can go deep into games, who can alleviate the pressure on the bullpen. The Padres absorbed Yu Darvish from Chicago, and it’s time to go to that well again. Heck, the Cubs could even take on some of that salary if they want, and pick from a higher tier of prospects from a Padres system that just doesn’t quit.
The match: Jameson Taillon, Cubs
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