The biggest prospect trades of the past 20 years

The Winter Meetings kicked off on Monday in Las Vegas, beginning a four-day event that concludes with the annual Rule 5 Draft on Thursday and could feature some blockbuster trades along the way.
Some of the biggest trades involving prospects in recent memory have transpired during the Winter Meetings. Notably, the Dec. 6, 2016, trade that sent White Sox ace Chris Sale to Boston put the Red Sox on track toward a World Series victory in 2018.
In return, the White Sox gained Yoán Moncada, MLB Pipeline's top prospect at the time, and right-hander Michael Kopech, now one of baseball's better pitching prospects, as well as two other prospects in a deal that helped to accelerate the club's rebuilding efforts. One day later, the South Siders traded Adam Eaton to the Nationals for Lucas Giolito, Reynaldo López and Dane Dunning.
In 2015, it was the D-backs that grabbed the headlines when they sent shortstop prospect Dansby Swanson, who they had drafted with the No. 1 overall pick in June, and Gold Glove-winning outfielder Ender Inciarte to the Braves in a deal for Shelby Miller. With the trade, Swanson became the first No. 1 overall pick to be traded the same year he was drafted, and the first to be dealt before reaching the Majors since Adrián González (2003).
Here's a chronological look at other elite prospects who have been traded and how those deals panned out. Keep in mind that each player's prospect rank refers to his spot on the Top 100 at the time of the trade, unless otherwise noted.
December 2018 -- Jarred Kelenic (No. 62 overall prospect), Justin Dunn (No. 89 overall): Traded from the New York Mets to the Seattle Mariners with Gerson Bautista, Jay Bruce and Anthony Swarzak for Robinson Canó and Edwin Díaz.
The Mets parted ways with their most recent first-round Draft picks in Kelenic (No. 6 overall in 2018) and Dunn (No. 19 in '17) to land Cano and Diaz. Kelenic has the higher upside of the two Top 100 prospects as a potential five-tool outfielder, but Dunn should be the first to arrive in the Majors after finishing his second full season in Double-A.
November 2018 -- Justus Sheffield (No. 31 overall): Traded from the New York Yankees to the Seattle Mariners with Erik Swanson and Dom Thompson-Williams for James Paxton.
After a September callup with the Yankees, Sheffield was dealt to the rebuilding Mariners in exchange for one of baseball's better left-handed starters in Paxton. It marked the second time in three seasons that Sheffield was traded, as he previously was sent from the Indians to the Yankees in the Andrew Miller deal in July 2016.
July 2018 -- Francisco Mejía (No. 15 overall): Traded from the Cleveland Indians to the San Diego Padres for Brad Hand and Adam Cimber.
Mejia had long been the subject of trade rumors before the Indians finally dealt him to the Padres in July 2018, in exchange for a pair of relievers. He raked for the Padres' Triple-A affiliate after the trade, and then homered three times in 21 games as a September callup.
January 2018 -- Lewis Brinson (No. 13 overall), Monte Harrison (No. 71 on 2018 Preseason Top 100): Traded from the Milwaukee Brewers to the Miami Marlins with Isan Díaz and Jordan Yamamoto for Christian Yelich.
Brinson was the obvious headliner in the blockbuster trade that sent Yelich, the 2018 NL MVP and batting champion, to Milwaukee, and then saw regular playing time in center field (when healthy) in his first season in Miami. Harrison, meanwhile, produced mixed results in Double-A during his first Marlins campaign, though his tools and overall upside are plenty intact.
August 2017 -- Franklin Perez (No. 46 overall): Traded from the Houston Astros to the Detroit Tigers with Daz Cameron, Jake Rogers and a PTBNL (Juan Ramirez) for Justin Verlander.
Perez has logged just 19 1/3 innings (all coming in 2018) since his acquisition by the Tigers at the 2017 waiver Trade Deadline. He missed the first nine weeks of the season due to a right lat strain and then landed on the shelf for good with right shoulder capsular inflammation in late July. Still just 21, Perez was added to the Tigers' 40-man roster in November.
July 2017 -- Dustin Fowler (No. 77 overall), Jorge Mateo (No. 47 on 2017 Preseason Top 100), James Kaprielian (No. 58 on '18 Top 100): Traded from the New York Yankees to the Oakland A's for Sonny Gray and international bonus slot money.
Fowler was the lone Top 100 prospect at the time of the trade, but all three prospects Oakland acquired in the deal had been featured on the list at some point that year. Mateo struggled in his first season with the A's, hitting just .230/.280/.353 over 131 games in Triple-A, but the speedster remains a dynamic talent with a high ceiling -- if he can put it all together. Kaprielian was recovering from Tommy John surgery at the time of the trade and has not pitched in a game since 2016. The A's added the right-hander to their 40-man roster in November, ahead of his age-25 season.
July 2017 -- Blake Rutherford (No. 30 overall): Traded from the New York Yankees to the Chicago White Sox with Ian Clarkin, Tito Polo and Tyler Clippard for Todd Frazier, Tommy Kahnle and David Robertson.
The Yankees' 2016 first-rounder was in the middle of a so-so first full season when he was dealt to the White Sox. Moving up to Class A Advanced Winston-Salem in 2018, Rutherford rebounded to slash .293/.345/.436 with 41 extra-base hits and 15 steals in 115 games.
July 2017 -- Eloy Jiménez (No. 8 overall), Dylan Cease (No. 63): Traded from the Chicago Cubs to the Chicago White Sox with Bryant Flete and Matt Rose for José Quintana.
Jimenez and Cease were named the White Sox Minor League hitter and pitcher of the year in 2018, which marked the first full season in the organization for both players. Jimenez put up monster numbers between Double-A and Triple-A, while Cease garnered MLB Pipeline Pitcher of the Year honors thanks to his dominant second half in Double-A. Jimenez is currently the No. 3 prospect on the Top 100, while Cease checks in at No. 25.
December 2016 -- Lucas Giolito (No. 3 overall), Reynaldo Lopez (No. 38): Traded from the Washington Nationals to the Chicago White Sox with Dane Dunning for Adam Eaton.
The Nationals dealt three of their top six prospects, including two in the Top 50 overall, to the White Sox as they looked to solidify their outfield for 2017. Both Giolito and Lopez made their Major League debuts in 2016 and have since emerged as staples in the White Sox starting rotation.
December 2016 -- Yoan Moncada (No. 1 overall), Michael Kopech (No. 67): Traded from the Boston Red Sox to the Chicago White Sox with Luis Alexander Basabe and Victor Diaz for Chris Sale.
The 2016 Winter Meetings blockbuster that netted the Red Sox ace Sale has been key in the White Sox rebuild. Moncada, 23, has underwhelmed with his strikeouts so far in the Majors, but still has a combination of power and speed that could make him a star if it all clicks. Kopech joined Moncada in the Majors in late 2018 and pitched well before requiring Tommy John surgery that will cost him all of '19.
August 2016 -- Lewis Brinson (No. 21 overall): Traded from the Texas Rangers to the Milwaukee Brewers with Luis Ortiz and a PTBNL for Jeremy Jeffress and Jonathan Lucroy.
Brinson played in 21 games with the Brewers in 2017 after the trade, and then became the key piece in the January 2018 deal with Miami that netted the club future MVP Yelich.
July 2016 -- Clint Frazier (No. 24 overall): Traded from the Cleveland Indians to the New York Yankees with J.P. Feyereisen, Ben Heller and Justus Sheffield for Andrew Miller.
Selected fifth overall in the 2013 Draft, Frazier seemed destined to become a fixture in the Indians' outfield in the coming years before they used him to land Miller at the 2016 Trade Deadline.
July 2016 -- Gleyber Torres (No. 26 overall): Traded from the Chicago Cubs to the New York Yankees with Rashad Crawford, Billy McKinney and Adam Warren for Aroldis Chapman.
The Cubs' abundance of young big league hitters, as well their need for a lockdown closer, led to Torres' inclusion in the Trade Deadline blockbuster for Chapman. He became the youngest MVP and batting champion (19) in that year's Arizona Fall League and then took second in the AL Rookie of the Year voting in 2018.
December 2015 -- Mark Appel (No. 43 overall): Traded from the Houston Astros to the Philadelphia Phillies with Harold Arauz, Thomas Eshelman, Brett Oberholtzer and Vincent Velasquez for Jonathan Arauz and Ken Giles.
Appel failed to live up to expectations after Houston made him the No. 1 overall pick in 2013, and then continued to struggle at Triple-A before surgery to remove bone spurs from his right elbow prematurely ended his campaign in 2016. After being designated for assignment following the 2017 season, Appel announced that he would take an indefinite break from baseball.
December 2015 -- Dansby Swanson (No. 10 overall): Traded from the Arizona D-backs to the Atlanta Braves with Aaron Blair and Ender Inciarte for Shelby Miller and Gabe Speier.
The D-backs' decision to move Swanson during the 2015 Winter Meetings was one of the more criticized deals in recent memory, as he became the first No. 1 overall Draft pick to be traded before reaching the Majors and the first ever to be dealt the year he was drafted. He's made strides in each season since joining the Braves while serving as the club's everyday shortstop.
November 2015 -- Manny Margot (No. 25 overall): Traded from the Boston Red Sox to the San Diego Padres with Carlos Asuaje, Javier Guerra and Logan Allen for Craig Kimbrel.
The Padres' rebuild began in earnest when they dealt Kimbrel for four quality prospects -- Margot the most notable of the bunch. Margot, Asuaje and Guerra all reached the Majors with the club, and Logan, currently No. 76 on the Top 100 list, seems poised to join the big league in 2019.
July 2015 -- Daniel Norris (No. 15 overall): Traded from the Toronto Blue Jays to the Detroit Tigers with Jairo Labourt and Matt Boyd for David Price.
Norris spent most of 2018 on the disabled list with a left groin strain and largely has been plagued with injuries since joining the Tigers. Over parts of four seasons with the club, the left-hander has compiled a 4.61 ERA in 252 innings.
July 2014 -- Addison Russell (No. 11 overall): Traded from the Oakland A's to the Chicago Cubs with Billy McKinney, Dan Straily and cash for Jason Hammel and Jeff Samardzija.
Russell was a starter for the NL All-Stars and posted a .738 OPS with 21 home runs and 95 RBIs for the World Series champions in 2016, though he's struggled to produce similar results in 2017-18 and will miss the first 40 games in 2019 due to suspension.
December 2013 --Tyler Skaggs (No. 10 on 2013 Preseason Top 100): Traded as part of three-team trade by the Arizona D-backs to the Los Angeles Angels.
Skaggs showed the stuff to become a frontline left-handed starter, but Tommy John surgery shelved him in 2014 and kept him out of action until July 2016. The left-hander turned in his best season to date in 2018, posting a 4.02 ERA while setting career highs in innings pitched (125 1/3) and starts (24).
December 2012 -- Trevor Bauer (No. 5 overall): Traded from the Arizona D-backs to the Cleveland Indians as part of a three-team trade with the Cincinnati Reds with Matt Albers and Bryan Shaw. Cincinnati sent Didi Gregorius to Arizona and Drew Stubbs to Cleveland, which sent Lars Anderson and Tony Sipp to Arizona, and Shin-Soo Choo, Jason Donald and cash to Cincinnati.
The former 2011 No. 3 overall Draft pick has became a stalwart in the Indians' rotation and was especially good in 2018, his first All-Star campaign. Overall, Bauer established career bests in ERA (2.21) and strikeouts (221) while logging at least 175 innings for a fourth straight year. He finished sixth in the AL Cy Young voting.
December 2012 -- Wil Myers (No. 3 overall): Traded from the Kansas City Royals to the Tampa Bay Rays with Patrick Leonard, Mike Montgomery and Jake Odorizzi for Wade Davis, James Shields and a PTBNL.
Things started out well for Myers as he won AL Rookie of the Year honors in 2013, but he struggled to stay healthy the following year, prompting the Rays to deal him to San Diego during the offseason. With the Padres, Myers has produced a .252/.330/.454 line with 77 homers and 66 steals over 455 games.
January 2012 -- Jesus Montero (No. 12 overall on 2012 Preseason Top 100 list): Traded from the New York Yankees to the Seattle Mariners with Hector Noesí for Jose Campos and Michael Pineda.
Montero started out as an offensive-minded catching phenom, then moved to first base permanently in 2014 when his defense never improved, all the while posting a .693 OPS in the big leagues.
December 2011 -- Jarrod Parker (No. 26 overall on 2012 Preseason Top 50): Traded from the Arizona D-backs to the Oakland A's with Ryan Cook and Collin Cowgill for Craig Breslow, Trevor Cahill and cash.
When healthy, Parker showed glimpses of becoming the type of frontline starter many saw in him when he was a first-round pick in 2007. Sadly, two Tommy John surgeries, followed by a third elbow injury, led to his eventual retirement.
July 2010 -- Justin Smoak (No. 9 overall on 2010 Preseason Top 50): Traded from the Texas Rangers to the Seattle Mariners with Matt Lawson, Blake Beavan and Josh Lueke for Cliff Lee and Mark Lowe.
The 2008 first-round pick drew early comparisons to Mark Teixeira but struggled to live up to the hype before breaking out with a career-high 38 home runs in 2017, which he followed with 25 (his second-highest total) in 2018.
December 2007 -- Cameron Maybin (No. 3 on 2008 Preseason Top 50) and Andrew Miller (No. 19 on 2007 Preseason Top 50): Traded from the Detroit Tigers to the Florida Marlins with Dallas Trahern, Burke Badenhop, Frankie De La Cruz and Mike Rabelo for Miguel Cabrera and Dontrelle Willis.
Maybin has been traded six times in his career, most recently going from the Marlins to the Mariners in November 2016. Altogether, he's been a 13.5 WAR-player (Baseball Reference WAR) over parts of 12 seasons in the Majors.
July 2007 -- Elvis Andrus (No. 38 overall on 2008 Preseason Top 50) and Jarrod Saltalamacchia (No. 32 on 2007 Preseason Top 50): Traded from the Atlanta Braves to the Texas Rangers with Neftalí Feliz, Matt Harrison and Beau Jones for Ron Mahay and Mark Teixeira.
Saltalamacchia was the higher-ranked prospect at the time of the trade, but it's been Andrus, the AL Rookie of the Year Award runner-up in 2009, who has had the better career, highlighted by a pair of All-Star Game selections.
2005 -- Andy Marte (No. 9 overall on 2006 Preseason Top 50): Traded from the Atlanta Braves to the Boston Red Sox for Edgar Renteria and cash. Traded from the Boston Red Sox to the Cleveland Indians with Guillermo Mota, Kelly Shoppach, cash and PTBNL for Josh Bard, Coco Crisp and David Riske in January 2006.
Perhaps the poster child for "can't miss" prospects who did just that, Marte logged just over 850 big league at-bats with a .634 OPS.
July 2004 -- Scott Kazmir (No. 4 overall on 2005 Preseason Top 50): Traded from the New York Mets to the Tampa Bay Devil Rays for Bartolome Fortunato and Victor Zambrano.
Kazmir did finish ninth in the 2005 Rookie of the Year voting, but had a bit of an uneven career until really finding his groove in 2014 and becoming a key rotation piece for several teams in the subsequent years.
January 2002 -- Carlos Pena (No. 5 overall on 2002 Preseason Top 100, per Baseball America): Traded from the Texas Rangers to the Oakland A's with Mike Venafro for Jason Hart, Gerald Laird, Ryan Ludwick and Mario Ramos.
Pena was traded again five months later in a three-team trade after struggling through 40 games for the A's. He averaged 21 homers from 2003-05 in Detroit before being released and then had the best years of his 14-year career with Tampa Bay from 2007-10, when he averaged 36 homers and 102 RBIs.
March 2000 -- Drew Henson (No. 14 on 2002 Preseason Top 100, per Baseball America): Traded from the New York Yankees to the Cincinnati Reds with Jackson Melian, Brian Reith and Ed Yarnall for Mike Frank and Denny Neagle. Traded back to New York with Michael Coleman for Wily Mo Pena in March 2001.
Henson got a grand total of nine big league at-bats over two years for the Yankees before pursuing an NFL career.
December 1998 -- Pablo Ozuna (No. 8 on 1999 Preseason Top 100, per Baseball America): Traded from the St. Louis Cardinals to the Florida Marlins with Braden Looper and Armando Almanza for Edgar Renteria.
Ozuna spent the better part of two seasons in Double-A after he was traded to Florida, reaching the big leagues for the first time late in 2000. He would go on to hit .282/.318/.359 over 309 games in his seven-year career.