List of worst NBA contracts reflects poorly on Otis Smith, Magic

Otis Smith's tenure as the Orlando Magic's president of basketball operations ended in May when he and the team mutually agreed to part ways, but Bill Simmons' list of the league's worst contracts, posted Friday at Grantland, serves as a reminder of some of Smith's missteps.

Among the contracts Simmons selected, Smith is responsible for those of Jason Richardson, Glen Davis, and Rashard Lewis. He later traded Lewis for Gilbert Arenas, another player on Simmons' list, on whom he would ultimately use the amnesty provision to waive after a half-season with the Magic. He also traded for Hedo Türkoğlu, another player who appears on the list.

Davis, the only member of Smith's greatest-hits still with the Magic, joined the team in a sign-and-trade deal with the Boston Celtics. He's owed $6.4 million in the 2013/14 season and $6.6 million in 2014/15. All of that money is fully guaranteed, with no player or team options. The veteran power forward was averaging 15.1 points and 7.2 rebounds before breaking a bone in his left foot in February. He will likely miss the balance of the season.

Simmons listed Davis in the "overpaid role players" category, a group which also includes Brandon Bass, the player the Celtics received in the sign-and-trade deal involving Davis.

Lewis' contract is the most infamous one that Smith awarded during his time with the Magic. The most sought-after free agent in the summer of 2007, Lewis had one All-Star season with the Magic before tailing off dramatically. Simmons weighs in:

"Who was Smith bidding against for Lewis that summer? We don't know. Why did he pay Lewis $50 million more than he was worth? We don't know. Why hasn't anyone hired Otis since Orlando fired him last year? We don't — oh, wait, we know."

Smith traded Lewis to the Washington Wizards for Arenas, a deal which made little sense at the time and made even less sense once Arenas actually took the floor for the Magic. The combo guard averaged eight points on 34.4 percent shooting in 44 regular-season appearances. Over the next two seasons, Orlando will pay him more than $40 million not to play.

Smith sign-and-traded Türkoğlu to the Toronto Raptors in 2009 as the veteran forward reached an agreement on a five-year deal worth more than $50 million. Smith didn't want to overpay Türkoğlu and had, one month earlier, acquired Vince Carter via trade; Türkoğlu would have been overpriced and redundant on that team.

A little more than a year later, Smith acquired Türkoğlu and Richardson from the Phoenix Suns for a package including Carter, Marcin Gortat, and a future draft pick. Simmons lauds Türkoğlu's "dignity" for being suspended for performance-enhancing drugs, which suspension saves the Magic some money.

Richardson is owed $16 million over the next three seasons. He signed that deal with the Magic prior to the 2011/12 season, but Rob Hennigan, Smith's successor in Orlando, traded Richardson to the Philadelphia 76ers in August. Richardson, now 32, will miss the balance of the season as he recovers from an operation on his left knee.

The only Magic player to appear on Simmons' list whom Smith didn't have a hand in acquiring is Al Harrington, who arrived from the Denver Nuggets in the Dwight Howard trade. Simmons lists Harrington in the "overpaid role players" section along with the likes of Davis and Bass. Only 50 percent of Harrington's contract is guaranteed over the next two seasons, giving Hennigan some trade flexibility.

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