A Trade Deadline deal can alter the course of a franchise in more ways than one.
Acquiring a proven veteran can aid a team’s final push toward the postseason and even provide the missing piece for a World Series championship. But those trades almost always require sending away a top prospect or two – if not more.
The 10 trades below involve 13 impact players from this season who were top-five prospects in their organizations (per MLB Pipeline) when they were dealt during Deadline season. While not every top prospect included in a trade goes on to big league success, the players below did.
In some cases, their former organizations are haunted by what might have been, but in others, short-term success made a deal worth it.
So with trade talks percolating ahead of this year’s July 31 Deadline, let’s take a look back.
Organizational prospect rankings are listed in parentheses.
CJ Abrams, MacKenzie Gore and James Wood, Nationals
The trade (Aug. 2, 2022): Nationals trade Juan Soto and Josh Bell to Padres for Abrams (No. 1), Gore (No. 4), Robert Hassell III (No. 2), Jarlin Susana (No. 19), Luke Voit and Wood (No. 5)
There is no Juan Soto in this trade market or, typically, any other. Soto was still 2 1/2 years from free agency when he was traded by Washington after he rejected a long-term extension. And we got the answer to a question that probably won’t come up again for a while: How much does it cost to acquire a 23-year-old superstar with that much club control?
Well, so far, it has cost San Diego three All-Stars – Abrams was one in 2024, and Wood and Gore this year – not to mention two prospects who remain among the team’s best.
The Padres reached the NLCS in 2022 but missed the playoffs the following year before trading Soto to the Yankees in December 2023 and returning to October the following year. The Nationals have failed to take advantage of their influx of young stars and sit in last place in the NL East, so this trade may not yet have a clear winner.
Dylan Cease, Padres
The trade (July 13, 2017): White Sox trade José Quintana to Cubs for Cease (No. 4), Bryant Flete, Matt Rose and Eloy Jiménez (No. 1)
Cease was not the centerpiece of this return, and it looked like the White Sox could have multiple foundational pieces after Jiménez hit 31 home runs as a 22-year-old rookie in 2019. Alas, Jiménez could never repeat that production. Chicago traded him to Baltimore last July, the Rays signed him this past offseason, and he was released earlier this month without making it up to the Majors.
Cease, however, fulfilled his potential even as the White Sox severely regressed following postseason appearances in 2020 and 2021. He finished second in American League Cy Young voting in 2022 and became the headliner in another trade when he was dealt to the Padres before the 2024 season.
Quintana helped the defending-champion Cubs back to the playoffs in 2017 and pitched on the north side for three more seasons. He’s now with Milwaukee, his sixth team in five seasons.
Jazz Chisholm Jr., Yankees
The trade (July 31, 2019): Marlins trade Zac Gallen (No. 19) to Diamondbacks for Chisholm (No. 4)
The rare prospect-for-prospect trade ended up benefiting both teams. This was Gallen’s second trade – he was dealt from the Cardinals, along with 2022 National League Cy Young winner Sandy Alcantara and two others, to Miami for Marcell Ozuna in 2017.
Unlike Chisholm, Gallen had already reached the Majors at the time of this trade, with a 2.72 ERA and 43 strikeouts in seven starts. His inclusion in a trade at this stage of his career was surprising, but the Marlins may have felt like they had a surplus of starting pitching with young starters such as Alcantara, Pablo López, Caleb Smith and Trevor Richards.
Chisholm became an All-Star in Miami in 2022, then clubbed 19 homers the following season before being traded to the Yankees at the 2024 Trade Deadline. He’s an All-Star again in 2025, while Gallen, a 2023 All-Star, is enduring his worst season, with a 5.40 ERA in 20 starts.
Pete Crow-Armstrong, Cubs
The trade (July 30, 2021): Cubs trade Javier Báez and Trevor Williams to Mets for Crow-Armstrong (No. 5)
With the benefit of hindsight, we can wonder how four Mets prospects ranked ahead of Crow-Armstrong at the time. But four years ago, he was far from a finished product, even though his hitting, fielding, throwing and speed were ranked 55 or better on the 20-80 scouting scale. Limited by the pandemic and injury, PCA had played just six professional games between the 2020 Draft and this trade.
We know now that as Crow-Armstrong has fulfilled each one of those prognostications and vastly improved his 40-grade power, it’s difficult to rank four NL players ahead of him. He seems to be keeping pace with Shohei Ohtani as a favorite to win MVP, and he’s providing just about as many highlight-reel moments as the Dodgers’ two-way icon.
The Mets missed the playoffs in 2021, even with excellent contributions from Báez and Williams. After three rough seasons in Detroit, Báez is helping lead a Tigers resurgence, and he made his third All-Star appearance in 2025. The former shortstop is now playing the same position – center field – as Crow-Armstrong.
Jeff Hoffman, Blue Jays
The trade (July 28, 2015): Rockies trade LaTroy Hawkins and Troy Tulowitzki to Blue Jays for Miguel Castro (No. 7), Hoffman (No. 4), Jose Reyes and Jesús Tinoco
Even though multiple top 10 prospects changed teams, this trade was all about the shocking switch of shortstops – especially that of Tulowitzki, who had spent his entire 10-year career in Colorado. A career .299 hitter at the time of the trade, the then-30-year-old Tulowitzki played just 243 more games and batted .249, though he hit 24 homers in 2016 as the Blue Jays reached the ALCS.
Reyes also struggled to make an impact with his new team, batting .259 with a .659 OPS in 47 games with the Rockies before returning to the Mets -- the franchise for whom he made four All-Star teams while leading the NL in triples four times, stolen bases three times and hits once -- for the final three years of his career.
Hoffman has come full circle, signing with Toronto in free agency this past offseason. He was an All-Star for the Phillies in 2024 and has found a home as a reliever after making the permanent conversion from starting pitcher in 2022. His 23 saves rank third in the AL, but he has a 4.79 ERA thanks in part to nine home runs allowed in 41 1/3 innings.
Sean Manaea, Mets
The trade (July 28, 2015): Athletics trade Ben Zobrist to Royals for Aaron Brooks and Manaea (No. 2)
The Royals pulled off the type of trade every fan base dreams about. Needing help at second base and in the outfield and looking to return to the World Series after falling in seven games to the Giants in 2014, Kansas City acquired a switch-hitter who could play just about anywhere – including second base and the outfield.
Not surprisingly, it paid off. Zobrist had an .813 OPS down the stretch for Kansas City and had 20 hits in the postseason as the Royals defeated the Mets for their first championship in 30 years. KC also got quality innings from another trade acquisition, Johnny Cueto. Zobrist won the World Series the next year, too, with the Cubs, when he was Series MVP.
While Manaea delivered quality innings for the Athletics, Giants and Mets, finishing 10th in Cy Young voting for New York last season, flags fly forever; acquiring Zobrist helped raise a banner in Kansas City.
Grant Holmes, Braves, and Frankie Montas, Mets
The trade (Aug. 1, 2016): Athletics trade Rich Hill and Josh Reddick to Dodgers for Jharel Cotton (No. 9), Holmes (No. 4) and Montas (No. 5) – Aug. 1, 2016
Montas was traded twice as an organization's top five prospect – he first went to the Dodgers from the White Sox when he was ranked No. 3 in Chicago’s system in December 2015. This was Montas’ third trade in three years, and those deals, including one from the Red Sox in 2013, included 19 players.
Montas’ best years so far came in Oakland. Though he battled injuries there, he had a 3.57 ERA in 72 games from 2018-2021 and finished sixth in AL Cy Young voting in 2021, when he made a career-high 32 starts. Holmes finally made his MLB debut in 2024 after a decade in the Minors, and he’s making up for lost time, leading this year’s Braves in starts and strikeouts.
For three top-10 prospects, the Dodgers got 47 subpar games from Reddick, who helped the Astros beat the Dodgers in the World Series the following season. Hill fared much better with Los Angeles; he signed with them as a free agent before the 2017 season and won 30 games there in 3 1/2 seasons, striking out 427 batters in 361 1/3 innings. The 45-year-old signed a Minor League contract with the Royals in May.
Josh Naylor, Diamondbacks
The trade (July 29, 2016): Padres trade Andrew Cashner, Tayron Guerrero and Colin Rea (No. 6) to Marlins for Carter Capps, Luis Castillo, Jarred Cosart and Naylor (No. 2)
This trade includes three players producing for playoff contenders in 2025 and is the rare deal in which the Marlins trade prospects for an established Major Leaguer. The Marlins were 55-48 on July 29, 2016, in second place in the NL East and within striking distance of a playoff spot. This trade did not help them, though. Cashner had a 5.98 ERA for the Marlins, who finished 79-82 and out of the postseason.
Naylor was the Marlins’ first-round pick in 2015 and was traded in another Deadline deal from San Diego to Cleveland in 2020. Naylor was among six players sent to Cleveland in a deal centered around starting pitcher Mike Clevinger. His trade along with Castillo, who has become a top-of-the-rotation starter, is one of several franchise-altering deals made by the Marlins in the past decade.
Rea is a key part of a Cubs rotation that has been hampered by injuries in 2025, but he didn’t provide much value for the Marlins, with one appearance in 2016. He didn’t pitch in the Major Leagues again for four years, re-emerging with the Cubs, followed by three years in Milwaukee and one in Japan.
Tyler O’Neill, Orioles
The trade (July 21, 2017): Cardinals trade Marco Gonzales to Mariners for O'Neill (No. 2)
O’Neill proved to be solid defensively and a threat on the bases, but his prospect status was based on one overwhelming trait – his power. O’Neill smashed 32 home runs in the Minors in 2015, 24 in 2016, 31 in 2017 and 26 in 2018 before making his debut with the Cardinals.
As has become a theme, O’Neill struggled to stay off the injured list, but he broke out with 34 home runs for St. Louis in 2021. When healthy, O’Neill remains a power threat, as evidenced by his 31 homers for the Red Sox in 2024. He is perhaps best known for his ongoing streak of hitting a home run on Opening Day for six straight years.
Gonzales won 61 games for the Mariners and topped 143 innings in four of five full seasons. But he was never an All-Star and didn’t make a single postseason start.
Gleyber Torres, Tigers
The trade (July 25, 2016): Yankees trade Aroldis Chapman to Cubs for Rashad Crawford, Billy McKinney (No. 6), Torres (No. 1) and Adam Warren
This is the first of two straight Deadlines in which the Cubs traded their top prospect, and this one came with the most reward. Chapman allowed just three earned runs down the stretch for the Cubs, striking out 46 batters in 26 2/3 innings with a fastball that still reaches triple digits nearly a decade later.
You might remember that 2016 ended with the Cubs breaking a 108-year World Series championship drought by beating Cleveland in seven games. Chapman gave up the tying runs in Game 7 on a two-run homer by Rajai Davis in the eighth inning, but he held Cleveland scoreless in the ninth to set up the Cubs’ 10-inning win.
Chapman signed back with the Yankees the following season and spent six more years in the Bronx. He is an All-Star this season for the eighth time. Torres made the All-Star team in his first two years with the Yankees and was back in the Midsummer Classic as a starter in 2025, his first season with the Tigers.