12.Gilbert Arenas — Six Years, $111 million
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Arenas left $16 million on the table when he inked a six-year, $111 million contract with the Washington Wizards in 2008.

So, um…this could have been worse?

It’s remarkable that the Wizards agreed to such a commitment following a season in which Arenas played just 13 games because of knee injuries. He logged only two contests in the first year of his new deal, missed 50 more games the following season and was then traded for Rashard Lewis and his own albatross salary.

Arenas agreed that his contract might have been the worst in NBA history, but it wasn’t a true max. So he gets off on a technicality.