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No other professional sport can match the intrigue of MLB’s trade deadline, and between the pace and the magnitude of the deals, this year did not disappoint.
All teams want to make good deals, but the best are the “win-win” trades in which both sides benefit. Coming from a former general manager, here are five trades that caught my eye as win-wins at this deadline.
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New York Yankees acquire 2B Jazz Chisholm from the Miami Marlins for prospects C Agustin Ramirez, SS Jared Serna and 3B Abrahan Ramirez
I foresaw the Yankees acquiring Chisholm in a deal, but this turned out different than I anticipated. Still, I love this deal for New York; the Yankees add an athletic, versatile, energy player who doesn’t make much money and offers 2.5 years of club control. And wow, has he been on fire, with four home runs in his first three games in pinstripes, already good for +0.6 fWAR. The Yankees are 3-0 in those games.
Chisholm has volunteered to play third base, has experience at SS, 2B and CF, and will be buoyed moving from a tough hitter’s park in Miami to a left-handed hitter’s haven in the Bronx. Furthermore, with this addition, New York addressed a need for speed — Anthony Volpe (18 SB) is the only other Yankee with more than five steals on the season — while balancing a right-handed-heavy lineup. They did all this without trading anybody from their MLB club or giving up any of their top-10 prospects.
The deal also makes sense for the Marlins — if a few things happen. If Agustin Ramirez (now No. 5 on Miami’s top-30 mlb.com prospect list) can stay at catcher, where he has thrown out only 9% (9/99) of baserunners this season, the 20 homers produced by his bat in 87 games between Double-A and Triple-A could plug an organizational black hole. If Serna (No. 9 on the Marlins’ prospect list) and his average tools can stay at shortstop and continue to hit, he could reach Miami next season. If Abrahan Ramirez (not ranked) can find a position — only 20 years old, he has already moved off short to third, but he had nine errors in 63 chances — his career .454 OBP (!) could make him an intriguing offensive player.
For now, the Marlins must live in the world of if, the world of upside. The NL East is a scary place. The Atlanta Braves have won six straight division titles. The Philadelphia Phillies are the best team in MLB in 2024. The New York Mets are inevitable, loaded with talent and money. The Washington Nationals have been reloading with a young nucleus and a multitude of top prospects. Miami can’t match the talent or spending of the other four teams in its division, so the Marlins have to take chances and make this type of trade.
San Diego Padres acquire RHP Jason Adam from the Tampa Bay Rays for prospects RHP Dylan Lesko, OF Homer Bush Jr. and C J.D. Gonzalez
I thought San Diego might use Lesko to acquire a pitcher, but this trade wasn’t quite what I had in mind. While Adam is a former Padre, having signed as a minor-league free agent in 2017, he pitched in one game in Double-A before being released. He then bounced around MLB from 2018 to ’21, allowing 41 earned runs over 78⅓ innings with the Royals, Blue Jays and Cubs. Naturally, once in Tampa Bay, he gained superpowers and, from 2022 to ’24, recorded a 2.30 ERA over 164 2/3 IP. Pure and simple, Adam is one of the best setup men in MLB right now, and he’s under control for the next two seasons. This acquisition, combined with San Diego’s trade for Tanner Scott, gives the Padres a nasty back-end bullpen primed for a playoff push.
This is also an upside trade for Tampa Bay. Lesko (now No. 5 on Tampa’s top-30 mlb.com prospect list) has No. 1-starter upside and is 24 months removed from being selected 15th overall in the MLB Draft after having Tommy John surgery two months earlier. He has a 6.46 ERA with 52 walks in 69 1/3 IP in High-A, but if Tampa Bay could fix Adam — and countless others — think what the Rays can do with Lesko. Bush (No. 20 on the Rays’ prospect list) has a lower ceiling but higher floor than Lesko and looks like an extra MLB player with speed, plate discipline and positional versatility. Gonzalez (No. 28) is a lottery ticket, still 18 years old, taken 98th in the 2023 draft, with the ability to stick at catcher, but will he hit enough?
This deal comes down to Adam for Lesko, but ultimately, it’s about San Diego GM A.J. Preller. The Padres are not boring; they are a fun and talented team loaded with superstars. Preller is not boring; he’s willing to do anything at any time if he thinks it will help his team. Since May, he has traded away six of San Diego’s top nine prospects: No. 3 Robby Snelling, No. 4 Lesko, No. 6 Adam Mazur, No. 7 Dillon Head, No. 8 Grant Pauley and No. 9 Jacob Marsee. That’s not even counting the March deal for Dylan Cease that cost the Padres top-10 system prospects Drew Thorpe, Jairo Iriarte and Samuel Zavala.
All of this might not work, but Preller knows it’s about 2024 for his squad, and he can and will find more prospects. The Padres are an exciting and dangerous team fighting for the playoffs, and Preller’s pushing all his chips to the middle.
It’s rare to see prospect-for-prospect challenge trades, especially at the deadline, but the Red Sox and Pirates pulled one off. Boston has three upside arms who are controllable until 2028 in Tanner Houck, Kutter Crawford and Brayan Bello. If the Red Sox can improve Priester, taken 18th overall in the 2019 draft and long ranked among the top-100 prospects in MLB, as they have Houck, Cutter and Bello, there’s real upside here. That’s important in the short term and long term for Boston because Nick Pivetta and James Paxton are free agents, and Lucas Giolito and Garrett Whitlock face injury questions. Also, the Red Sox have a top-heavy system with three elite prospects but only one pitcher ranked among their top seven prospects: Wikleman Gonzalez (No. 5), who has a 6.04 ERA in Double-A. Priester fills a big need.
Yorke was drafted one pick earlier (No. 17) and one year later (2020) than Priester. He has a lower ceiling but a higher floor than Priester. The Pirates have some recency bias here, as they are no doubt more intrigued by Yorke’s .898 OPS at Triple-A than they were dismayed by his .691 OPS repeating Double-A. That said, Yorke has improved every year as a pro, won’t turn 23 until next April, is knocking on the door of MLB and could be a Martin Prado-type contributor if it all comes together. His upside, youth, athleticism and hit tool could be impactful for a Pirates club on the rise.
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In this swap, Boston and Pittsburgh were trading from areas of strength. The Red Sox have top prospect shortstop Marcelo Mayer (ranked No. 7 overall) dominating Double-A and likely to be in Boston by 2025. They also have Vaughn Grissom, a right-handed-hitting 2B/OF like Yorke, who was hurt earlier in 2024 and has struggled recently. At the big-league level, Trevor Story, who might slide to second when Mayer is ready, is under club control through the 2028 season.
Likewise, the Pirates have an enviable MLB troika of starting pitchers with Paul Skenes, Mitch Keller and Jared Jones. Top prospect RHP Bubba Chandler will make it a four-piece band at some point in 2025. Johan Oviedo (+1.8 fWAR, 177.2 IP in 2023) and top-five organizational prospect Mike Burrows should also be back from injuries early in 2025. This trade made sense for both organizations, and it displays how Boston and Pittsburgh are both building for the future while competing for the playoffs in 2024.
This fascinating trade is sort of a combination of the previous three trades, another 3-for-1 deal with prospect-for-prospect elements and creativity from both teams. The Brewers drafted Lucas Erceg 46th overall in the 2016 draft as a third baseman. Five years later, he converted to pitching. Two years after that, he was acquired for cash by the Athletics.
Erceg’s Baseball Savant page has more red than an Alabama Crimson Tide football game: He throws hard (98th percentile in MLB with a 98.5 mph average fastball) and produces weak contact (99th percentile with an 85.2 mph average exit velocity). Yes, Erceg walks too many people (47th percentile with an 8.3% walk rate), but he has shown major improvement in that area year over year in MLB (last year, he ranked in the third percentile at 14.3%). Power arms at the back end of bullpens are the stuff that GMs dream about, and Erceg is a plus athlete with room to grow. Even better, he has just one year of MLB service time, so he won’t be a free agent until 2030.
So why would the Athletics trade him? The A’s will be in Sacramento in 2026 and (likely) Las Vegas in 2030. They’re a lot like the Marlins and Rays; they must play on the margins and be creative, seeking value in uncommon ways, which was how and why they got Erceg in the first place. With this trade, it’s not so much that Oakland is betting against Erceg as it is that the A’s are selling high on found money; pitchers in the 98th percentile of velocity tend to get hurt and maintain inconsistent performance levels. The A’s could’ve kept Erceg because he’s an elite setup man or even a closer — if Mason Miller moves to the starting rotation or sustains any injury — but this team isn’t likely to compete for years, and Erceg’s value will be less a year from now because he’ll have one less year of club control. And if anything went wrong in that time, well, Oakland couldn’t afford that risk.
Instead, the A’s added three new names to their prospect ranks. Mason Barnett (now No. 6 on Oakland’s top-30 mlb.com prospect list) is 23 years old and was Kansas City’s minor-league pitcher of the year in 2023. He has been lights-out in Double-A in July (1.64 ERA, 27 SO in 22.0 IP) and has legitimate middle-of-the-rotation upside as soon as next season. As the A’s move toward a brighter future, they need to do it with pitchers like Barnett. Will Klein (No. 15 on the A’s prospect list) has a chance to be what Erceg has become — a powerful, late-inning arm with great stuff if he can harness his control and command. Dickey (No. 28) is likely a versatile, fourth outfielder type at the MLB level, though he lacks impact tools and has always struggled vs. LHP.
Kansas City had a fantastic offseason and is a legitimate playoff contender. Adding Erceg is a risk worth taking for the Royals, one that is fiscally responsible and further solidifies an area of strength. Erceg joins a bullpen that includes setup man and trade acquisition Hunter Harvey and closer James McArthur. Harvey, acquired from the Nationals on July 14, ranks in the 97th percentile with a 97.8 mph average fastball. McArthur averages only 95.1 mph on his fastball but ranks in the 95th percentile with a 4.4% walk rate and in the 92nd percentile with a 54.3% groundball rate. It might not be Wade Davis, Greg Holland and Kelvin Herrera, but this bullpen is pretty damn good. The Royals should be a fun team to watch down the stretch and, hopefully, into the playoffs.
Following in the footsteps of Axel Foley, Kirk Gibson and Matthew Stafford, Jack Flaherty makes the trek from the Motor City to the City of Angels. For Flaherty, who starred for prep powerhouse Harvard-Westlake, it’s a homecoming. For the Dodgers, who landed the best rental starting pitcher without trading anybody from their MLB club or giving up any of their top-10 prospects, it’s a coup. For the Tigers, who reportedly had to navigate a nixed deal — the Yankees reportedly backed out after reviewing Flaherty’s medical records — it’s a value proposition calculation.
Whatever Flaherty’s medicals say, he has been absolutely dominant this season, pitching to a 2.95 ERA with 133 strikeouts and 19 walks in 106 2/3 IP, good for a +2.5 fWAR. That includes a 1.53 ERA in July. There are no noticeable lefty-righty splits here, and Flaherty has been better on the road (2.57 ERA) than at home (3.50 ERA) this season. He has a career 2.78 ERA at Dodger Stadium, with six walks and 36 strikeouts in 22 2/3 innings. He sure looks healthy, and even if he needs time to rest for the postseason, that’s a luxury Los Angeles can likely afford, given their 5.5-game lead in the NL West and 83.5% chance to win the division, according to FanGraphs. Accordingly, Flaherty’s acquisition is more about lining up a top-of-the-rotation starter for a playoff run than it is about getting to the postseason.
If a deal with the Yankees fell apart late, that would’ve put the Tigers in a tough position with the other teams rumored to have interest in Flaherty: the Dodgers, Padres and Red Sox. The Padres basically ran out of prospects — they weren’t going to trade their top two (Ethan Salas and Leodalis De Vries) for a rental — and might not have been able to absorb Flaherty’s prorated $14 million salary. Likewise, the Red Sox wouldn’t include any of their top three prospects, all of whom are ranked top-25 in MLB by mlb.com, in this type of deal. So for Detroit, it likely came down to the talent they could get from the Dodgers and the money they could save by trading Flaherty (roughly $4 million) versus the competitive balance pick they would’ve received if they’d kept Flaherty and made him a qualifying offer. That’s not an easy decision with the clock ticking as the trade deadline approaches.
Of course, the Tigers made the deal with the Dodgers. Thayron Liranzo (now No. 5 on Detroit’s top-30 mlb.com prospect list) is a switch-hitting catcher with power and patience, and he just turned 21. He showed up on some industry top-100 prospect lists this past offseason after a breakout year in the hitter-friendly Low-A California League, where he played more than half the season at 19 years old. Yes, the defense needs to improve with Liranzo, who has thrown out only 15% (14/95) of baserunners this season, and yes, he’s much better as a left-handed hitter, but he has a track record and some offensive upside at a young age. Add Trey Sweeney (No. 24 on Detroit’s prospect list), who was drafted 20th in 2021 by the Yankees, and I think the Tigers made the right call.
The Tigers made a brilliant move to sign Flaherty this past offseason. He pitched well for them and provided more long-term value to the organization through the acquisition of Liranzo and Sweeney. This is a win-win deal, but make no mistake: It’s a bigger win for the Dodgers. If the Dodgers win a World Series this fall, Flaherty will likely be a key part of it. And now he has the chance to do it in his hometown.