Ranking the Best Prospects Traded at the MLB Deadline in the Last 100 Years
Trade deadline deals are the sport’s most tempting game of “what if.” Sometimes it’s a veteran rental who makes a playoff push possible. But every so often, it’s the throw-in prospect who ends up sticking around the longest.
Since 2000, a handful of these swaps rearranged futures by launching All-Stars, award winners, and franchise staples in the process. Here’s a look at some of the most notable prospect swaps since the start of the century.
Cliff Lee’s Rare Dual Status
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It’s rare for a prospect to become so good that they get traded twice more for top prospects. But Cliff Lee pulled it off. He was first dealt in 2002 as a relatively unknown piece in the Bartolo Colon blockbuster, but turned into an ace with a Cy Young and 43.2 WAR, then became coveted trade bait himself.
James Wood Powers Into the Picture
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When the Nationals traded Juan Soto, they got several pieces, but Wood has started to draw the most buzz. Now 22, the outfielder has shown major upside, including a 486-foot homer this year. CJ Abrams and MacKenzie Gore were also in the return, but Wood still had prospect status, so he made the cut.
Elvis Andrus Headlines a Bold Texas Swing
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In 2007, Texas shipped Mark Teixeira to Atlanta and got back a hefty return, including a teenage shortstop with smooth hands. Andrus went on to play for over a decade in Arlington while helping fuel the club’s early 2010 playoff runs. Two All-Star nods and nearly 2,000 hits later, that deal aged pretty well.
Brandon Phillips Blooms in Cincinnati
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The Colon trade continues to echo through time. Phillips was part of that same 2002 Montreal-to-Cleveland deal and didn’t stick until 2006 with the Reds. There, he earned three All-Star nods, four Gold Gloves, and produced nearly all of his 28.9 WAR across more than a decade.
Gleyber Torres for a Championship Push
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When the Cubs were chasing their 2016 World Series dream, they sent Gleyber Torres to the Yankees for Aroldis Chapman. It worked, and Chapman closed out history. But Torres, still a prospect at the time, later made two All-Star teams with New York. Both sides got what they needed, just on different timelines.
Scott Kazmir’s Controversial Exit
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There are trades fans forget. Then there’s the Kazmir-Zambrano deal. In 2004, the Mets moved a prized lefty arm for a middling starter, and the reaction was not kind. Kazmir quickly thrived in Tampa by earning All-Star nods and a playoff start. His 25.4 WAR made the return look smaller with every passing season.
Carlos Carrasco’s Under-The-Radar Rise
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When the Phillies traded Cliff Lee to Cleveland in 2009, Carrasco was the key prospect in return. He needed time to establish himself, but became a mainstay in Cleveland’s rotation for a decade. Across multiple comeback stories, he posted 26.4 WAR, all with the Guardians.
Justin Smoak’s Prospect Hype, Short Impact
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When the Mariners landed Justin Smoak for Cliff Lee in 2010, the hype was hard to miss. He’d been a top-15 prospect and switch-hit with power. But he never quite found his footing in Seattle. A late-career spark in Toronto (38 homers in 2017) gave the trade a little shine, but not much.
Grady Sizemore Rounds Out a Legendary Trade
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The 2002 Bartolo Colon trade sent three prospects to Cleveland. One became a Cy Young winner. Another became an All-Star second baseman. And then there was Sizemore—briefly, the brightest of the trio. With elite defense and 30-30 potential, he racked up 27.8 WAR before injuries dimmed the lights.
Yoan Moncada Shifts the Sox
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Boston wanted Chris Sale in 2016. Badly. To get him, they gave the White Sox Yoan Moncada, the No. 1 prospect in baseball at the time. Sale helped deliver a championship. Moncada brought a strong 2019, hinting at stardom, but health setbacks and inconsistency have made his trajectory harder to chart.
Francisco MejíA’s Hype Outpaced Results
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Cleveland’s trade for Brad Hand in 2018 cost them Mejía, a highly rated catching prospect. San Diego hoped for a long-term backstop but only got flashes. Mejía never became a lineup fixture.
J.P. Crawford’s Delayed Value
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Crawford went from the Phillies to the Mariners in a 2018 trade centered around Jean Segura. At the time, he was viewed more as a project than a cornerstone. But he developed into a reliable everyday shortstop, eventually winning a Gold Glove.
Jarred Kelenic Headlines a Reversed Regret
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Kelenic went from the Mets to the Mariners in a 2018 deal for Edwin Díaz and Robinson Canó. Though he never reached his superstar ceiling, the Mets’ side of the trade aged poorly. Kelenic’s modest value still outpaced much of what New York got in return.
Dylan Cease Rises After a Bold Flip
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The Cubs needed a controllable starter and sent José Quintana to the White Sox in 2017. Chicago returned Dylan Cease and Eloy Jiménez. While Eloy showed pop, it was Cease’s 2022 breakout—2.20 ERA and a Cy Young runner-up finish—that made this deal stand out.
Triston Casas Stays Put—For Now
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Boston has held onto Casas through multiple deadlines, despite interest. While not traded, he’s a counter-example: a prospect many assumed would be moved but wasn’t. His slow but steady development path shows how some organizations are willing to be patient and protect their top-tier talent.