8 Outrageous Trades to Shake Up the 2024 MLB Trade Deadline

8 Outrageous Trades to Shake Up the 2024 MLB Trade Deadline0 of 8

Vladimir Guerrero Jr.Steve Russell/Toronto Star via Getty Images

This past Thursday, our Joel Reuter put together an updated list of 10 trade ideas for Major League Baseball’s July 30 trade deadline. It was good, sensible stuff, involving a lot of the names you’ve been hearing as top trade candidates over the past three months.

For today, though, let’s get a little weird with it.

Contrary to what is sure to be popular belief in the comments, “Outrageous Trades” doesn’t mean “Intentionally Moronic Proposals.” We’re not about to suggest Aaron Judge getting traded to the Marlins, Gunnar Henderson relocating to the Rockies or anything like that.

By outrageous trades, we mean swaps that would raise some serious eyebrows because of their magnitude, but trades that might actually be agreeable to all parties involved.

And yes, that use of “all” parties instead of “both” parties is intentional.

What’s an outrageous trades article without a few deals involving at least three teams?

In fact, let’s get things started out right with a doozy of a three-teamer.

Note: Prospect rankings reflect where players stood in B/R’s most recent farm system rankings, which were published on June 21.

White Sox Load up the Farm in a 3-Team Shuffle1 of 8

Luis Robert Jr.Duane Burleson/Getty Images

Chicago White Sox Receive: OF Jasson Domínguez (NYY No. 1 prospect), C Jeferson Quero (MIL No. 2 prospect), IF Tyler Black (MIL No. 3 prospect), RHP Chase Hampton (NYY No. 4 prospect), SS Cooper Pratt (MIL No. 9 prospect), LHP Brock Selvidge (NYY No. 10 prospect)

New York Yankees Receive: OF Luis Robert Jr. (from CHW), LHP Hoby Milner (from MIL)

Milwaukee Brewers Receive: LHP Garrett Crochet (from CHW), OF Alex Verdugo (from NYY)

These aren’t the teams you’ve grown accustomed to seeing in the market for Chicago’s two biggest trade chips. Been a lot of talk of the Phillies and Mariners on the hunt for Robert, and plenty of scuttlebutt about the Padres and Orioles wanting Crochet. The Dodgers would love to have them both.

Make no mistakes about it, though: The Yankees want to add at least one more bat and the Brewers sure could use a starting pitcher, considering they recently traded for and immediately deployed Dallas Keuchel for a rough outing.

Perhaps they can join forces for a three-team blockbuster that should expedite the White Sox rebuild?

Frankly, this might not even be enough prospect capital on Chicago’s end of the deal. It’s a bit more than what the Nationals got for the package of Juan Soto and Josh Bell two years ago, but we’re also talking about 3.5 years of team control on (when healthy) one of the better sluggers in baseball and 2.5 years of a sudden ace who could be tabbed to start the All-Star Game.

It might do the trick, though. And pairing catcher Jeferson Quero with unrelated catcher Edgar Quero in the same farm system would be fun.

As far as the two 2024 contenders in this deal are concerned, the Yankees would instantly upgrade an already great outfield to one of the best ever assembled while pre-addressing the possibility that Juan Soto doesn’t re-sign with them this offseason. And after adding Robert, Verdugo becomes a dispensable, expiring asset they could flip to the Brewers for a left-handed reliever.

Verdugo could give the Brewers some lineup depth, or maybe they just turn around and try to swap him for another starting pitcher. But Crochet would instantly become the ace of a staff seemingly held together by sticks, Band-Aids, smoke and mirrors. Between adding a great starting pitcher and hopefully getting Devin Williams back before much longer, Milwaukee could solidify itself as a World Series contender.

Injury-Plagued Orioles Loosen the Purse Strings2 of 8

Max ScherzerRichard Rodriguez/Getty Images

Baltimore Orioles Receive: RHP Max Scherzer and RHP Josh Stephan (Double-A prospect, not top 10 in Rangers farm system)

Texas Rangers Receive: RHP Félix Bautista

Scherzer finally made his 2024 debut last weekend against the Royals, carrying a perfect game into the fifth inning, no less.

But was it too little, too late for the reigning champs?

The Rangers are eight games back in the wild-card picture (and would need to leapfrog six teams) and 9.5 games back in the AL West.

It’s not a hopelessly insurmountable margin, but it’s not a promising one.

It does just about become insurmountable if that’s still where they’re sitting a month from now.

All 12 teams who made the playoffs last season were at least tied for a postseason spot at the end of play on July 31. Similar story in 2022, save for Cleveland making up a one-game deficit in the AL Central and St. Louis closing a three-game gap in the NL Central.

Chasing down a foe from eight-plus games back in two months’ time has been done on occasion. And if any team could do it, you would assume it’s one that should be getting all of Josh Jung, Jacob deGrom, Tyler Mahle and Evan Carter back from the IL soon-ish.

However, Scherzer moving in a deadline deal for the third time in four years wouldn’t be completely shocking at this point.

And Baltimore does need to swing big on the pitching front, unless it thinks a back of the rotation of Albert Suárez and Cade Povich will be enough to catch the Yankees in the AL East and/or win a postseason series after losing Kyle Bradish, John Means and Tyler Wells to Tommy John surgery.

Scherzer may be the answer to their problem, and they just might be able to get him and a decent pitching prospect for their on-the-mend, flame-throwing closer, as adding Bautista pretty well addresses what is shaping up to be Texas’ biggest offseason concern.

But the O’s Don’t Stop There3 of 8

Mason MillerEakin Howard/Getty Images

Baltimore Orioles Receive: RHP Mason Miller

Oakland A’s Receive: 2B Connor Norby (BAL’s No. 7 prospect), OF Dylan Beavers (BAL’s No. 9 prospect), RHP Seth Johnson (BAL’s No. 10 prospect)

Well, if the Orioles are giving the Rangers the guy who’s supposed to be their closer from 2025-27, they’re going to be pretty motivated to bring in another incredible closer to replace him, right?

The Athletic’s Ken Rosenthal recently reported that Oakland’s asking price for Mason Miller is “going to be absurd,” which we’ve also been saying for the past two months. He might/should be an All-Star and is going to be under team control for another five seasons beyond the current campaign.

But with a loaded farm system, the Orioles are on the short list of teams who could reasonably put together a strong enough package to get Oakland to unload its most valuable trade chip.

Is this trio of prospects absurd enough for the A’s?

If not, maybe the O’s up the ante from Norby to 1B/3B Coby Mayo (No. 2 prospect)?

Because, really, with Gunnar Henderson, Jordan Westburg and eventually Jackson Holliday all under team control through at least 2028, how many infielders do the Orioles need?

(They also have No. 3 prospect Samuel Basallo, currently a C/1B hybrid who will presumably become primarily a first baseman if he wants to play for a team that has Adley Rutschman holding down the fort behind the plate.)

That doesn’t mean they’re willing to just give Mayo away, though. He still holds a ton of value for them as a top-25 overall prospect in baseball, even if it might be mostly trade value. But if that’s the cost for five-plus years of Miller, they might do it.

Marlins Help an NL East Rival4 of 8

Jazz Chisholm Jr.Reed Hoffmann/Getty Images

Philadelphia Phillies Receive: CF Jazz Chisholm Jr.

Miami Marlins Receive: OF Justin Crawford (PHI No. 4 prospect), SS Starlyn Caba (PHI No. 5 prospect)

Deadline deals between divisional rivals are relatively rare. Of the 40-plus trades that went down in the week leading up to last year’s deadline, there were only two between teams in the same division: The Pirates sent Carlos Santana to Milwaukee, and the Mets traded David Robertson to Miami.

There were a couple more than that the previous summer, but the only noteworthy one was the three-team deal between the Astros, Orioles and Rays, in which the non-AL East team was the one getting the biggest trade chip (Trey Mancini).

They do happen from time to time, though, so there’s no reason to assume the Phillies and Marlins would be unable to come to terms on a trade just because one is 24 games ahead of the other in the NL East.

These teams did broker a substantial swap not that long ago, too, when the Fish sent J.T. Realmuto in February 2019.

And if the Phillies can get the Marlins to the negotiating table, they would be mighty interested in acquiring Jazz Chisholm Jr.

Though Philly has the best record in the NL, its current LF/CF situation is a bit of a mess. Johan Rojas got demoted a few weeks ago. (He got called back up Saturday, but only because Kyle Schwarber and Bryce Harper both hit the IL.) Prior to a four-hit game Wednesday, Brandon Marsh had gone 36 contests without a home run, dropping his slugging percentage below .400. Whit Merrifield isn’t even slugging .300 for the year. Neither is Cristian Pache.

Chisholm isn’t having the best season of his career, but he has been healthy (for a change) and has been more productive than Philadelphia’s current options.

Moreover, he’s under team control for another two seasons after this one and is only making $2.6 million this season. That makes him a long-term solution, and a relatively inexpensive one for a team that already has the highest 2025 payroll on the books.

This, of course, means Miami’s asking price won’t be a pittance. The Phillies will need to swing big with two of what MLB.com rates as the top 100 prospects in baseball.

More Angels Join Shohei Ohtani on Other LA Roster5 of 8

Tyler AndersonKevork Djansezian/Getty Images

Los Angeles Dodgers Receive: LHP Tyler Anderson, IF Luis Rengifo

Los Angeles Angels Receive: OF Josue De Paula (LAD No. 2 prospect), RHP Nick Frasso (LAD No. 9 prospect), LHP Ronan Kopp (Double-A prospect, not top 10 in Dodgers farm system)

What makes this trade outrageous is the notion that these neighbors would even reach out to one another for help.

Excluding a couple of times that the Angels purchased a player from the Dodgers, these teams have made only two trades with each other in the past three decades, both occurring within a few days of each other in December 2014.

After the Dodgers more or less purchased Shohei Ohtani from the Angels this past winter, there’s probably even more lingering animosity than usual.

But with Mookie Betts injured and Gavin Lux in a season-long slump, the Dodgers could certainly use a middle infielder. Goodness knows they could use a starting pitcher, too, with all of Yoshinobu Yamamoto, Walker Buehler, Clayton Kershaw, Tony Gonsolin, Dustin May and Emmet Sheehan presently on the shelf with no return dates particularly in sight.

Both Luis Rengifo and Tyler Anderson have another year remaining before free agency—Anderson for $13M, Rengifo’s 2025 salary to be determined in arbitration—but the Angels are already pretty well dead this season and are unlikely to contend next season, either. Both players should be available on the trade block and could fetch a nice return of prospects.

It would be kind of fun for the Dodgers to re-acquire Anderson, too. Prior to this season, the best of his career, by far, was his lone year with the Dodgers in 2022.

Of Course Atlanta Makes a Big Trade6 of 8

Jack FlahertyLeslie Plaza Johnson/Icon Sportswire via Getty Images

Atlanta Braves Receive: RHP Jack Flaherty, OF Mark Canha

Detroit Tigers Receive: RHP Hurston Waldrep (ATL No. 2 prospect)

Wheeling and dealing is the only life Atlanta GM Alex Anthopoulos knows, and a litany of marquee injuries has left one of the preseason World Series favorites needing to go back to that roster-building well once again.

They desperately need at least one outfielder, with Ronald Acuña Jr. (ACL) out for the year and Michael Harris II likely out until late July with a hamstring injury. And the back of the rotation has been a mess since trying to figure out life without Spencer Strider, lost to Tommy John surgery in early April.

But you know they’ll get some pieces.

It’s just a question of where they come from.

Getting Luis Robert Jr. and Garrett Crochet from the White Sox is the dream, but they don’t have enough in the farm system to pull off that type of blockbuster.

The other likely seller from the AL Central is the much more likely trade partner for Atlanta.

Jack Flaherty is having a remarkable bounce-back season on his one-year deal with the Tigers, quite possibly destined for the first All-Star Game of his career. And while Mark Canha is mired in a 39-game homer-less drought, the veteran corner outfielder has been a respectable hitter and could become the type of clutch several-month rental that Jorge Soler, Joc Pederson and Eddie Rosario were during Atlanta’s World Series run three years ago.

Hurston Waldrep had a brutal first go in the majors, making two starts earlier this month with a 16.71 ERA before landing on the IL with elbow inflammation. But he’s a highly touted prospect who could be a key piece of the Tigers rotation for the next few years alongside Tarik Skubal, Reese Olson and Casey Mize.

San Diego Padres Reunite with a Few Old Friends7 of 8

Seth LugoEakin Howard/Getty Images

San Diego Padres Receive: RHP Seth Lugo, RF Hunter Renfroe, 2B/RF Adam Frazier

Kansas City Royals Receive: RHP Adam Mazur (SDP No. 5 prospect), OF Homer Bush Jr. (SDP No. 10 prospect)

Remember two years ago, when the Baltimore Orioles got good out of seemingly nowhere, entered the trade deadline right in the thick of a wild-card race…and traded away Trey Mancini and Jorge López instead of making a push for what would have been their first playoff berth in six years?

Despite getting out to a 34-19 start and presently clinging for dear life to a wild-card spot, would it really be a surprise if the Kansas City Royals take a similar approach this summer?

Credit where it’s due, they went for it this past offseason, and it worked out way better than most of us expected. Save for the Dodgers and eventually the Giants, no team was more aggressive about bringing in new players in free agency than the Royals were, which immediately helped them improve upon what was a 106-loss disaster.

They may well end July with more wins than they had in the entire 2023 campaign.

But is this really a World Series contender?

Or do they have the funds/farm system to upgrade enough ahead of the deadline to keep pace with the World Series favorites?

We can debate the first question, but the answer to the latter is almost certainly not.

Thus, if they can use Seth Lugo’s sensational first three months of the season to A) upgrade what is currently one of the worst farm systems and simultaneously B) get out from under both Hunter Renfroe’s $7.5M player option for next season and Adam Frazier’s $8.5M mutual option (with a $2.5M buyout), that’s a win-win.

Lugo is owed another $15M next season, plus a $15M player option for 2026, so San Diego would ideally be upgrading the rotation for multiple seasons by bringing back these three former Padres.

Renfroe and Frazier haven’t been worth much this season, but positional depth has become a major issue for the Friars in the absence of Xander Bogaerts and now Fernando Tatis Jr. And if adding that depth for this season and the $10M to next year’s payroll helps decrease the amount of prospect capital Kansas City expects for Lugo, that’s also a win-win.

Adam Mazur has sputtered to a 7.25 ERA in his first five big league starts for the Padres, but the 2022 second-round pick has a lot of potential.

Toronto Burns It All Down in One Fell, Three-Team Swoop8 of 8

Vladimir Guerrero Jr.Maddie Malhotra/Boston Red Sox/Getty Images

Houston Astros Receive: 1B Vladimir Guerrero Jr. (from TOR), RHP Chris Bassitt (from TOR), OF Kevin Kiermaier (from TOR), LHP Parker Messick (from CLE)

Cleveland Guardians Receive: SS Bo Bichette (from TOR), LHP Yusei Kikuchi (from TOR), C Danny Jansen (from TOR), OF Colin Barber (from HOU)

Toronto Blue Jays Receive: RHP Cristian Javier (from HOU), OF Chase DeLauter (CLE No. 1 prospect), OF Jacob Melton (HOU No. 1 prospect), SS Brice Matthews (HOU No. 3 prospect), RHP Daniel Espino (CLE No. 4 prospect), RHP Jake Bloss (HOU No. 5 prospect)

Yes, the most outrageous part here might be the idea that Cleveland would ever be an aggressive buyer. We’re talking about a franchise that hasn’t been on the star power side of a significant deadline deal since, what, trading for Andrew Miller eight years ago?

Just go with it, though.

Technically, some exchange between Houston and Cleveland has to happen for this to be a three-team deal, or else it’s just a pair of simultaneous two-team swaps. So, sure, Houston flips the Guardians a Double-A outfield prospect and Cleveland sends a Double-A pitching prospect back to the Astros. Neither ranks top 10 in either team’s farm system. That part doesn’t really matter.

The main result is Houston upgrades what is currently a disastrous first base situation, gets a much-needed starting pitcher who isn’t on the IL and adds an experienced outfielder with a great glove.

Meanwhile, the Guardians do something about Brayan Rocchio’s sub-.300 slugging percentage, get a solid starter to replace Carlos Carrasco in the rotation—giving them the option of maybe pulling Logan Allen’s 5.72 ERA from the rotation if and when Gavin Williams is back—and add one more bat who can catch so they can stop playing Austin Hedges’ .435 OPS on a semi-regular basis.

Lastly, but maybe most notably, Toronto punts on the next 1.5 seasons to reload in a big way for 2026 and beyond, with a boatload of quality prospects and an established starting pitcher who is signed through 2027, but who is going to miss the rest of this season and possibly all of 2025 after recently undergoing Tommy John surgery.

Houston is giving up more capital than Cleveland in the deal, but the Guardians’ top prospect is regarded as a top-25 guy while the Astros’ top prospect is barely a top-75 guy. Houston is also getting more than Cleveland, as Guerrero is the more coveted of Toronto’s two big-name chips, while Bassitt still has a year left on his deal compared to Kikuchi being a few months away from free agency.

The moral of the story, though, is that Toronto has become the linchpin of this entire trade deadline.

If the Blue Jays embrace what is very clearly a seller’s market otherwise lacking in marquee names available, they could put together a monster of a trade / series of trades, likely getting more in return than the Nationals did for 2.5 years of Juan Soto two summers ago.

But if they don’t, it could be a pretty uneventful trade deadline.