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

MLB what-if No. 1: 2003 — Alex Rodriguez to the Boston Red Sox

There was so much drama in the months leading up to Alex Rodriguez’s trade to the Yankees that ESPN could put together a multi-part documentary series on everything that had occurred.

Amid his tenure with the Texas Rangers, Alex Rodriguez was working his way to becoming the clear best player in baseball. But after three consecutive losing seasons, Rodriguez desired something more: playing on a winning team.

Any team would want to acquire a talent like Rodriguez, but not all could take on his remaining $179 million contract. The Red Sox stepped up to the plate and pursued Rodriguez on the contingency that he would reduce his yearly salary by $4 million over the remaining seven years of the deal. Rodriguez agreed and the two teams had begun putting together the framework of the deal, with the likes of Manny Ramirez and Jon Lester discussed in the blockbuster trade along with the Chicago White Sox being added for a three-team transaction.

Everything seemed to go as planned until the union announced in mid-December that such a deal would not be approved. The Red Sox were certainly not pleased with the union’s decision.

“It is a sad day when the Players Association thwarts the will of its members,” Red Sox CEO Larry Lucchino said after the trade fell apart. “The Players Association asserts that it supports individual negotiations, freedom of choice, and player mobility. However, in this high-profile instance, their action contradicts this and is contrary to the desires of the player.”

Shortly after the deal collapsed, the Yankees swooped in to blindside the Red Sox and hijack the deal.

The proposed deal is still one of the most talked-about what-ifs in baseball history. Had the deal gone through, would the Red Sox still go on to win the 2004 World Series? Would A-Rod have delivered in clutch postseason situations in the same way Manny Ramirez did? Do the Yankees opt to acquire another power hitter on the market, like a Vladimir Guerrero Sr. or Miguel Tejeda? Would the Yankees and Red Sox rivalry still have reached the intensity it did in 2004 and 2005?

So many hypotheticals for such a and drama-filled transaction.