Chris Paul
It was tough putting Chris Paul on this list. He helped the Phoenix Suns return to relevancy as a driving force to the team making it to the 2021 NBA Finals. The Suns lost in six games to the Milwaukee Bucks, but none of that success would have been possible without Paul.
The Suns had to re-sign Paul in free agency. Had he left, the fan base would have turned on the organization, especially after the season he helped them to. But, from purely a financial standpoint, this was one of the worst deals signed this year in free agency.
Paul and the Suns agreed to a four-year, $120 million deal. Seeing a player who turned 36-years old before taking part in the NBA Finals this year landing a contract that pays $30 million annually is shocking. Committing to him through turning 40-years old is something that will always land on a list like this.
There is some saving grace with the contract not having as many guarantees later on, but it is still a lot of money for a player of this age to receive. Paul has also struggled with some injuries in years past, missing double-digit games in three out of the last five seasons.
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Keeping Paul was imperative to the franchise, but the amount of money that he signed for is still an eye-popping amount.