Honorable mentions: Ben Simmons, Philadelphia 76ers
The contract: 5 years, $170 million (2019)
Through the first few years of his career, Ben Simmons looked to be the supporting star that Joel Embiid was going to need to deliver a championship to the Philadelphia 76ers. So much so that the Sixers went all-in on Simmons and gave him a five-year, $170 million contract extension after the 2018-19 NBA season.
However, after that first season of the extension, Simmons completely fell off a cliff. Partly due to injuries, just two years after the contract extension, Simmons was a shell of himself as a player. He played just two seasons with the Sixers after the extension and held out that entire third year (due to injury, mental health, and a trade demand). He was eventually traded to the Brooklyn Nets and he has continued to struggle to find his former form.
This season in Brooklyn, Simmons is averaging seven points, seven rebounds, and six assists on 56 percent shooting from the field. Simmons is no longer a budding star and may be in consideration for the worst contract in the league. He still has two years remaining on the extension.