The 10 biggest what-if MLB trades that never happened since 2000

NEW YORK - APRIL 18: Alex Rodriguez #13 of the New York Yankees looks on against the Texas Rangers at Yankee Stadium on April 18, 2010 in the Bronx borough of Manhattan. The Yankees defeated the Rangers 5 - 2. (Photo by Rob Tringali/Sportschrome/Getty Images)
NEW YORK - APRIL 18: Alex Rodriguez #13 of the New York Yankees looks on against the Texas Rangers at Yankee Stadium on April 18, 2010 in the Bronx borough of Manhattan. The Yankees defeated the Rangers 5 - 2. (Photo by Rob Tringali/Sportschrome/Getty Images) /
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ATLANTA, GEORGIA – AUGUST 17: Clayton Kershaw #22 of the Los Angeles Dodgers stands in the dugout against the Atlanta Braves at SunTrust Park in the first inning on August 17, 2019 in Atlanta, Georgia. (Photo by Logan Riely/Getty Images) /

MLB what-if No. 6: 2007 — Clayton Kershaw to the Oakland Athletics

By the mid-season point of the 2007 season, the Dodgers were in a tightly contested division race with the Arizona Diamondbacks. The two teams went back-and-forth over the first half of the season for the division lead. As any general manager would do, Dodgers GM Ned Colletti looked to the trade deadline as a way to improve the team and gain an advantage over their division foes.

The team desperately needed a reliable third starter to have behind veterans Brad Penny and Derek Lowe. Colletti looked to multiple starters but had his eyes set on Oakland Athletics starter Joe Blanton. According to ESPN’s Buster Olney, the Dodgers discussed giving up “three frontline prospects” in the deal. Among the names mentioned were Clayton Kershaw, Matt Kemp and Andre Ethier.

The Dodgers were essentially faced with a dilemma that is all too familiar among front offices and how they evaluate a top prospect: trade him for an established starter or hope he lives up to his full potential. The Dodgers opted for the latter and declined the A’s steep asking price.

In the short-term, the deal would have helped the Dodgers considering they wound up dwindling down to an 82–80 fourth-place finish in the NL West. But in the long-term, they made the right decision to turn away Oakland’s offer. Kershaw went on to establish his status as arguably the best pitcher from the 2010s. Meanwhile, both Kemp and Ethier played a key role in the Dodgers’ rise to NL West dominance over the past decade.

Had this trade occurred, Oakland would have had one of the most lopsided trade wins in recent baseball history. Kershaw, Kemp and Ethier may have been just what the Athletics needed to become a serious World Series contender during their resurgence in the early 2010s.