Nathan Eovaldi
Nathan Eovaldi got away from the Dodgers what feels like a million times. The right-hander debuted with the Dodgers in 2011. He was drafted by LA and came up in the system. Then, he was traded to the Miami Marlins in the Hanley Ramirez deal in the middle of the 2012 season. He remained with Miami through the 2014 season and was then traded to the New York Yankees.
The Yankees released him after 2016, when he needed Tommy John surgery. Eovaldi then resurfaced with the Rays in 2018 before he was dealt to the Boston Red Sox midway through the season ... and the rest is history.
He helped take the Dodgers down in the 2018 World Series, then became a free agent this past offseason after Boston extended him in the wake of that Fall Classic. He was there for the taking and LA knew pitching was a massive priority for them. Instead, they let him sign a two-year, $34 million deal with Texas, and he's continued to thrive on the biggest stages in October.
Sure would've been nice had the Dodgers either kept him or reunited with him down the road. Their fortunes could've been very different between 2013 and now.