3. Anfernee Hardaway — 7 Years, $87 Million
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The longest contract in our top 10, Anfernee Hardaway’s huge post-lockout agreement didn’t go south right away.

He teamed with Jason Kidd in the Phoenix Suns’ big-name backcourt for a solid full season in 1999-2000, playing 60 games with averages of 16.9 points, 5.8 rebounds and 5.3 assists. His 17.9 PER and 54.9 true shooting percentage were higher than they were in either of his final two seasons with the Magic.

But then microfracture surgery reduced Penny, already a notch below his peak days with Orlando, to a shell of his former self.

He missed all but four games of the 2000-01 season before gradually transitioning to a bench role. His scoring average fell every year, dropping from 10.6 to 9.2 to 7.3…all the way down to 2.5 in his final year with the Knicks following a trade in 2003.

The quickness and fluidity of Hardaway’s game, the combination of loping strides and explosive bursts, were nearly gone before he signed with the Suns. As his post-Orlando career progressed, Hardaway’s body simply wasn’t capable of the feats it once was.

The Suns thought they were getting something spectacular when they signed Penny, with GM Danny Ainge calling him “the most skilled all-around player in the game,” and saying, “all of a sudden I really believe this puts us as one of the elite teams in the NBA,” per CBS News.

Neither turned out to be true. The Suns got an injured former star whose game deteriorated in every year of his contract.