3) NY Mets let free agent John Olerud walk away in his prime
This is a bit different. With John Olerud, he wanted to go back to his home state of Washington. The Seattle native would sign with the Seattle Mariners after the 1999 season. One of the league’s more underrated offensive and defensive players in the 1990s, he was a huge part of the success in Queens for his three seasons.
Olerud slashed .315/.425/.501 while in blue and orange. His .354 batting average from the 1998 campaign is still a team record. The 125 walks he drew in 1999 also remains unmatched.
It may have been impossible for the Mets to convince Olerud to stay because location mattered to him in free agency. Unless they were able to somehow get insight his head and implant false memories like Blade Runner or some other science fiction movie, it was never going to happen.
Olerud continued to produce for several more seasons on the Mariners roster. He put up similar numbers there. He’d also win three Gold Gloves.
Todd Zeile was the first man to replace Olerud at first base. He was good, but not quite up to snuff. Somewhat ironic, Olerud ended up back in New York at the end of 2004 when he was traded to the New York Yankees. By then Mets fans had already suffered through Mo Vaughn and some other first basemen.
Having Olerud on the 2000 Mets wouldn’t have changed the outcome of the World Series. It doesn’t take away from the fact that he should’ve stayed. If only we had the technology to fool him into believing he was raised on Long Island.