#2 Chris Bosh - Miami Heat - 2014

Just hours after LeBron James left the Miami Heat in the summer of 2014, Chris Bosh committed his future to the franchise by signing a new five-year, $118 million max extension. Bosh had excelled as a third option behind James and Dwyane Wade, although Miami's decision to give an aging Wade a five-year deal quickly came back to haunt them.

While Bosh put up his best numbers in a Miami uniform over the next two seasons, he was limited to just 97 appearances - and the former All-Star's final appearance came in 2016 following the discovery of a blood clot. Heat president Pat Riley has since admitted that it was a mistake to give Bosh a max deal rather than Wade, and the impact of Bosh's contract was felt as Miami fell out of playoff contention.
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#1 Chandler Parsons - Memphis Grizzlies - 2016

Back in the summer of 2016, Chandler Parsons signed a four-year maximum contract with the Memphis Grizzlies worth around $95 million. Parsons had averaged just 13.7 points and 4.7 rebounds with the Dallas Mavericks the prior season - and Memphis' decision to award the forward a max deal soon became disastrous for the franchise.
Parsons' first season in Memphis was impacted by knee injuries as the Florida native played just 37 times - averaging career lows in points (6.2) and rebounds (2.5). Injuries continued to impact Parsons over the next two years, and he would feature just 95 times (45 starts) before being traded to the Hawks in 2019. Parsons averaged 7.2 points, 2.6 rebounds, 1.8 assists while shooting just 39.3 percent from the field, and his deal is a prime example as to why NBA teams are now so fearful to commit to max extensions.
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