9. New York Knicks sign Carmelo Anthony to five-year, $120 million+ contract in 2014
The year 2014 was a strange time for the New York Knicks. Just one year in the past, they’d finished with the second-best record in the Eastern Conference and won their first playoff series in over ten years.
The Knicks followed that up with an underwhelming 37-45 record, leaving them on the outside looking in once the postseason rolled around. That summer, Phil Jackson and the front office signed star forward Carmelo Anthony to a new five-year, $124 million contract to stay in New York.
Anthony had landed in “The Big Apple” three years earlier via a trade with the Denver Nuggets. New York wound up in the playoffs each year he’d been in town, aside from the 2013-14 season.
Once the former Syracuse star signed the dotted line, things didn’t return to how they’d been in his first three springs in New York. Instead, the Knicks won just 17 games the following year, as Anthony missed 32 games mainly due to a torn left patellar tendon.
In the 2015-16 season, things went a bit better, but Melo’s Knicks still found themselves on the couch during the playoffs. It was almost the exact same story the following year, as New York won one less game and still failed to qualify for a shot at an NBA title.
And then that was it. Anthony was traded to the Oklahoma City Thunder ahead of the 2017-18 season, marking the end of his tenure with the Knicks. In his final two years in New York, Anthony averaged 21.8 and 22.4 points per game, respectively. Those averages were roughly five points worse than the numbers he put up ahead of the new contract in 2013-14.
This signing isn’t further up on the list because it is — after all — the NBA. Teams have to throw money at their stars to keep them happy. Unfortunately for the Knicks, Anthony alone wasn’t enough to bring the franchise any sort of success.