8. Stephon Marbury — 4 Years, $74 Million
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Stephon Marbury signed his four-year, $74 million extension with the Phoenix Suns in 2003, but ended up on the New York Knicks before it kicked in for the 2005-06 season. Good work by the Suns to get off that money before it started to hurt.

And hurt the Knicks it did, as Marbury repeatedly clashed with head coaches—from Lenny Wilkens to Larry Brown to Isiah Thomas to Mike D’Antoni—while suffering steady statistical decline. Marbury’s All-Star days were done by 2003, and his rocky tenure with the Knicks culminated in an indefinite suspension in December 2008. He and top executive Donnie Walsh couldn’t reach an agreement on a buyout figure until February 2009.

The Knicks paid Marbury roughly $88 million in his five years with the team and never won a playoff game.

Also, fun fact: One of the first-rounders New York surrendered in the trade to get Marbury, a 2010 lottery selection, turned into Gordon Hayward.

Marbury checks in above Francis because the Knicks could never find a trade partner and were stuck on the hook for all of Marbury’s contract until the buyout. Plus, the Francis situation never got as ugly as this one, which you can gauge from Marbury’s comments to Frank Isola of the New York Daily News in 2008:

I didn’t hear one of my teammates say, ‘Why isn’t Stephon Marbury playing? This is a good system for him, even to play with the second unit and bring more firepower.’ When things got bad and then worse, guys like Quentin Richardson say, ‘I don’t consider him a teammate. He let his teammates out to dry.’ He didn’t care I was his teammate when I was banished. They left me out for dead.