Who will sign the next mega-extension?

Aaron Judge, OF, Yankees, age 28
Eligible for free agency after the 2022 season

Unlike many of the game’s young stars, Judge’s age might work against him; he’ll be entering his age-31 season when he first hits free agency. Judge’s impact on the Yankees’ lineup isn’t in question, but his ability to stay healthy is an issue. If the Yankees decide to extend one player, Torres seems like a better bet than Judge for both his age and durability.

Juan Soto, OF, Nationals, age 22
Eligible for free agency after the 2024 season

Soto is widely considered the best pure hitter in the game, so it would make sense for the Nationals to do whatever it takes to keep him in Washington for a long time. But with three more arbitration-eligible years before he becomes a free agent, Soto could set arbitration salary records if he continues to produce at his epic levels. Boras might view Soto as the only player who could approach (or pass?) Mike Trout’s record $426.5 million deal, so locking him up before he has a chance to test the market feels unlikely.