Ranking the Best MLB Offseason Trades Since 2000

David KenyonFeatured ColumnistDecember 5, 2020

Ranking the Best MLB Offseason Trades Since 2000

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    Eric Gay/Associated Press

    The trade deadline is always most exciting, but MLB teams occasionally strike a massive deal in the quiet of the offseason.

    Since 2000, several clubs have bolstered their rosters with a superstar or key piece for a championship run. For example, the 2007 Boston Red Sox added two critical contributors to a World Series-winning team in one offseason trade.

    But not every franchise can win a title. Though that's always the goal, the Detroit Tigers—without a World Series championship since 1984—have twice picked up a superstar who later earned a Triple Crown or Cy Young Award.

    This ranking considered both individual success and the impact a player had on team accomplishments.

Honorable Mention: Francisco Liriano, Joe Nathan to Twins

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    MATT SLOCUM/Associated Press

    Things didn't go as planned for the San Francisco Giants.

    Shortly after the 2003 season, they shipped reliever Joe Nathan and prospects Francisco Liriano and Boof Bonser to the Minnesota Twins for catcher A.J. Pierzynski. He lasted one year with the Giants, who missed the playoffs by a game.

    In fairness to San Francisco, there isn't a lasting image of Nathan and Liriano celebrating a World Series with Minnesota. But this is about as lopsided as it gets.

    Nathan became a closer, earned four All-Star nods in the next six season and still owns the franchise record with 260 saves. Liriano landed an All-Star appearance and finished third in American League Rookie of the Year voting in 2006 and won 50 games in his Twins career.

12. Roy Halladay to Phillies

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    Matt Slocum/Associated Press

    Following a 2008 World Series title, the Philadelphia Phillies fell to the New York Yankees in the 2009 Fall Classic. Philly's response? Acquire one of baseball's top pitchers.

    Philly parted with three valuable prospectsTravis d'Arnaud, Kyle Drabek and Michael Taylorbut none managed even a sizable impact with the Toronto Blue Jays. Despite not winning a World Series after adding Halladay, the Phillies won the trade.

    Halladay won 21 games and the National League Cy Young Award in 2010 and then finished second in the voting the next season. He also garnered the final two of his eight career All-Star trips in 2010 and 2011.

11. Christian Yelich to Brewers

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    Aaron Gash/Associated Press

    When the Miami Marlins embraced a fire sale before the 2018 season, the Milwaukee Brewers took full advantage. They brought in Christian Yelich for prospects Lewis Brinson, Isan Diaz, Monte Harrison and Jordan Yamamoto.

    Roy Halladay's tenure with Philadelphia and Yelich's time with Milwaukee is awfully similar.

    Yelich has a National League MVP Award and a second-place finish with two All-Star nods. The Brewers lost in the National League Championship Series once and the division series once, just like the Phillies. Yelich also has won a pair of Silver Slugger honors with Milwaukee.

10. Josh Donaldson to Blue Jays

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    Kathy Kmonicek/Associated Press

    Right as Josh Donaldson entered his prime, the Blue Jays snagged him from the Oakland Athletics. Toronto sent Brett Lawrie and three other players to the A's in November 2014.

    Donaldson wasted no time providing an incredible return, winning the AL MVP in his first season with the Jays. He paced the American League with 122 runs (which also led MLB), 123 RBI and 352 total bases, hitting a career-best 41 doubles and 41 home runs in 2015.

    In three-plus years, Donaldson went to a pair of All-Star games and secured two Silver Sluggers. He belted 116 homers for Toronto.     

9. Mookie Betts to Dodgers

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    Sue Ogrocki/Associated Press

    Mookie Betts is challenging to rank considering his post-trade sample size is only one shortened season. At the same time, the Los Angeles Dodgers won the World Series.

    This blockbuster with the Boston Red Sox paid off exactly as they hoped.

    In February, the Dodgers sent Alex Verdugo and prospects Jeter Downs and Connor Wong to the Sox for Betts and David Price. Price opted out of the season because of the coronavirus pandemic, but Betts suited up and played a pivotal role.

    He finished second in NL MVP voting and earned Gold Glove and Silver Slugger awards. His bat and defense showed up in major ways during the postseason too. Most notably, his home run late in Game 6 of the World Series helped the Dodgers seal their first title since 1988.

8. Max Scherzer to Tigers

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    Patrick Semansky/Associated Press

    A first-round pick of the Arizona Diamondbacks in 2006, Max Scherzer left the organization as part of a three-way trade in December 2009. As the Yankees added Curtis Granderson and the D-Backs picked up Ian Kennedy, the Tigers acquired Scherzer.

    Granderson excelled for a couple of years, and Kennedy had one outstanding season, but Scherzer developed into an ace.

    During five years with Detroit, he posted an 82-35 record with a 3.52 ERA. Scherzer won the 2013 AL Cy Young Award, secured two All-Star appearances and formed a devastating tandem with Justin Verlander.

    The Tigers won four straight division titles from 2011 to 2014, but they won just one AL pennant, were swept in the 2012 World Series, lost two American League Championship Series and were swept in a division series.

    Still, Scherzer was a superstar.

7. Curt Schilling to Red Sox

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    NICK WASS/Associated Press

    For many baseball fans, you already know: the Bloody Sock.

    That moment defined Curt Schilling's four-year stay with Boston, as his seven-inning, one-run start in Game 6 of the 2004 ALCS opposite New York is a piece of MLB history. He also notched a win to help the Red Sox sweep the Cardinals in the World Series and snap the franchise's 86-year title drought.

    With the Sox, Schilling earned an All-Star nod, a second-place AL Cy Young Award finish and a 6-1 record in eight playoff appearances. Boston celebrated two championships, and Schilling won both his World Series starts.

    All that after a November 2003 trade of Mike Goss, Casey Fossum, Jorge De La Rosa and Brandon Lyon. It's yet another reminder that proven stars can be so much more valuable than prospects.

6. Josh Beckett and Mike Lowell to Red Sox

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    Lenny Ignelzi/Associated Press

    The Florida Marlins had already won a title with Jose Beckett and Mike Lowell, and they received Hanley Ramirez and Anibal Sanchez in return when they dealt the pair to the Red Sox in a seven-player swap. So, this November 2005 trade wasn't as lopsided as many others.

    Still, Boston won its second championship in four years thanks to major contributions from the former Florida stars.

    During the 2007 regular season, Lowell and Beckett earned All-Star nods. Beckett finished second in the AL Cy Young Award race, and Lowell finished fifth in AL MVP voting. In the playoffs, Beckett went 4-0 and allowed four runs in 30 innings for a 1.20 ERA. Lowell secured World Series MVP honors with a 1.300 OPS.

    Beckett added two more All-Star appearances for the Sox, while Lowell spent another three years with Boston before retiring.

5. Jim Edmonds to Cardinals

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    GEORGE NIKITIN/Associated Press

    Jim Edmonds began his career with the California Angels, who dealt him to the St. Louis Cardinals in March 2000. The center fielder cost the Cardinals Kent Bottenfield and Adam Kennedy—a small price to pay for a legendary piece.

    Along with Albert Pujols and Scott Rolen, Edmonds propelled the Cardinals to a World Series title in 2006.

    Known for his defensive excellence, Edmonds won six Gold Glove Awards with the Redbirds. But he was also a feared hitter; Edmonds' 241 homers rank fourth in franchise history. He twice finished in the top five in MVP voting, adding a Silver Slugger Award and three All-Star nods with St. Louis.

    Edmonds entered the Cardinals Hall of Fame in 2014.

4. Anthony Rizzo to Cubs

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    David Banks/Associated Press

    Anthony Rizzo experienced two offseason trades on his journey to prominence. The first time, he moved from Boston to the San Diego Padres in the Adrian Gonzalez deal of 2010. The next offseason, San Diego dealt him to the Chicago Cubs for Andrew Cashner.

    Since then, Rizzo has merely established his place as one of the most important figures in franchise history.

    Rizzo played an integral part in the Cubs snapping a 108-year championship drought. Along with hitting .360 in the 2016 World Series, he gloved the final out of Game 7.

    During nine seasons to date, Rizzo has cranked 228 homers, made three All-Star teams and tallied four Gold Gloves in Chicago.    

3. Alex Rodriguez to Yankees

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    Chris O'Meara/Associated Press

    Before he joined the Yankees in February 2004, Alex Rodriguez had seven All-Star appearances, seven Silver Sluggers, two Gold Gloves and the season before had finally won an MVP Award. He'd played for the Seattle Mariners and Texas Rangers and departed the latter in exchange for Alfonso Soriano and Joaquin Arias.

    Looking back, we know Rodriguez acknowledged using performance-enhancing drugs from 2001 to 2003. And in 2014, A-Rod didn't play because of a season-long suspension related to his involvement in the Biogenesis scandal. You can perceive that however you'd like.

    On the field, though, he kept producing.

    Rodriguez made seven All-Star teams with the Yankees, won two MVPs and claimed three Silver Sluggers. New York won a title in 2009. Rodriguez tallied 351 homers with 1,096 RBI over 12 seasons with the Yanks.

2. Adam Wainwright to Cardinals

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    MORRY GASH/Associated Press

    Born and raised in Georgia, Adam Wainwright was seemingly destined to have a storybook career as a first-round pick of the Atlanta Braves. Instead, a December 2003 trade shipped Wainwright, Ray King and Jason Marquis to the Cardinals for J.D. Drew and Eli Marrero.

    Atlanta made a colossal mistake. Drew produced in 2004 but left in free agency, and the Braves soon traded Marrero.

    Wainwright, on the other hand, turned into a cornerstone of 15 seasons for a two-time World Series champion.

    As a rookie reliever, he got the final out of the 2006 World Series. Wainwright has since been a fixture of the rotation, racking up four top-three NL Cy Young Award finishes, three All-Star trips, two Gold Gloves and even a Silver Slugger.

    He missed the 2011 championship run because of Tommy John surgery, but that's simply a footnote in his career. Wainwright has the third-most wins in franchise history.

1. Miguel Cabrera to Tigers

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    Tony Gutierrez/Associated Press

    In a ranking that values team accomplishments, Miguel Cabrera is difficult to peg. Detroit has made only four playoff appearances and won one AL pennant without a World Series title during his 13 seasons.

    His accomplishments, however, are overwhelming.

    Acquired with Dontrelle Willis from the Marlins in December 2007 for Cameron Maybin, Andrew Miller and four others, Cabrera was a force.

    During the next nine seasons, he averaged 38 doubles, 34 homers, 114 RBI and 77 walks with only 103 strikeouts. "Miggy" hit .325 with a .404 on-base percentage in that span. He won back-to-back AL MVP Awards in 2012 and 2013—including the Triple Crown in 2012—following three straight years of top-five finishes. He collected seven All-Star honors and five Silver Slugger Awards.

    Father Time is undefeated, and Cabrera's production has dropped in recent years. But he's bound for the Hall of Fame.