Top-10 Free Agency Fails Of All-Time

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10. Peja Stojakovic 2006 Hornets – 5 yrs/$64 million

While his decline wasn’t as sharp as some of the names coming up, Peja’s biggest NBA contract also signaled the beginning of the end for his relevance as a star.

Just two years removed from MVP contention, Stojakovic had regressed into a painfully one-dimensional shooter, even before an ill-timed back injury kept him on the shelf for most of his first year in New Orleans. Never quite the same after, Peja’s numbers slowly tapered off as he became more of a liability in almost every regard but his trademark long-ball.

9. Larry Hughes 2005 Cavaliers – 5 yrs/$70 million

One of many futile moves made in an attempt to appease King James of Akron, Hughes was imported from the Wizards and paid lavishly, as though he had done something more than leech off Gilbert Arenas’ monopolization of opposing defenses.

Hughes was coming off an apex season, but his 22ppg belied his terrible shooting – which sat near the 40% mark for his career, and his nearly 3 steals/game were an outlier; twice what he’d ever average again. His Cleveland era was scarred by half-hearted defense, and shot selection that inspired one pleading Cavs fan actually create the website

The Cavs finally got rid of him in 2008 (trading his bloated contract for another one you’ll see coming up on this list), but the damage had mostly been done, and LeBron Decided to bail on this sad scene. At least for a bit. 

8. Hedo Turkoglu 2009 Raptors – 5 yrs/$53 million

The Toronto Raptors of the 2000’s were a mostly-pitiful lot of teams, their struggles characterized by a lack of toughness and shitty defense. Never was this more apparent than in 2009, when the Raptors, trying to convince Chris Bosh to stick around, inked Hedo to flank him and Andrea Bargnani (‘lol’) in the frontcourt.

His past two seasons in Orlando had been impressive (in a system tailored perfectly to his game), but Hedo was a late bloomer entering his decline who couldn’t guard a newborn Pug. The Raptors predictably hemorrhaged points all year, while Turkoglu basically forgot to break character from his Pizza Pizza commercial. He was traded the following season to avoid a public lynching by angry Torontonians.

This was one of several moves Colagelo botched on his way to an awkward dismissal as GM, and not the last time you'll see him on this list...

7. Amar’e Stoudemire 2010 Knicks – 5 yrs/$99 million

If this list were based solely on results, Amar’e would no doubt land much higher. But even at the time, this was a desperate, precarious, and very James Dolan way to spend “one hundred million dollars”. Having whiffed on LeBron after spending half a decade trying to clear cap room, the Knicks panic-grabbed Stoudemire to avoid total revolt at MSG.

The move saved face at first; Amar’e was a beast, but his own body (and to a lesser extent Melo’s arrival) tamed his game quickly. Meanwhile his back-loaded deal kept growing like The Blob: next season, finally its last = $23.42 million.

6. Ben Wallace 2006 Bulls – 4 yrs/$60 million

The warning signs were there. Although Wallace was coming off a Mutombo-esque 4th DPOY award, he was an aging star, and a heavily one-way player whose game relied on strength and mobility. Already severely undersized as a center – just 6’9” beneath the afro – it was a safe bet the then-32-year-old would begin to fall off sometime soon.

“Sometime” came far sooner than the normally-stingy Bulls could’ve hoped for and they justifiably bailed on Big Ben in year two @ $15 million per. The Cavs bore the burden of his hefty tab - having dumped Larry Hughes on Chicago - until the 2009 Shaq trade with Phoenix, who paid him to not play for them.

5. Anfernee Hardaway 1999 Suns – 7 yrs/$87 million

Before he was blowing free agent signings in Toronto, Colangelo was blowing free agent signings in Phoenix – although he managed to get at least one right - like this expensive nightmare that came right on the heels of a trying lockout, and the continued decay of Hardaway’s knees. (It helps when your dad owns the team).

What happened to Penny’s career was downright sad, but there was no need to pen another tragic act to his story by giving him a pricey deal over the max length when his legs clearly could no longer carry much of a load (59, 19, 50 games in prev. 3 seasons). Hardaway was never close to the player he was pre-injury, or what Colangelo had hoped by ambitiously giving him that kind of money.

4. Raef Lafrentz 2002 Mavs – 7 yrs/$70 million

One of Mark Cuban’s less-savvy investments, LaFrentz appears on this list with a slight asterisk, having actually arrived in Dallas via trade 27 games before the Mavs inked him to one of the most preposterous contracts in NBA history. Its significance couldn't be ignored.

Lafrentz performed deceptively well following the deadline deal, leading Cuban to sink seven years’ worth of eight figures into his surgically-repaired ACL. No sooner was he paid, Raef’s NBA ability began rapidly eroding; his numbers (and overall mobility) steadily declining to his retirement before this contract could run its course.

3. Jerome James 2005 Knicks – 5 yrs/$30 million

Making the token appearance from the Isiah Era Knicks is Jerome James, the guy who played one good playoff series, got a $30 million dollar deal, and literally became twice the player. Most of Thomas’ other abominable acquisitions came via trade, but this one became emblematic of the Knicks’ persistent money incineration like no other.

Rather than try and earn the money he’d just made, Jerome went about spending his new fortune in an attempt at the Guinness World Record for Burger King consumption. His best numbers were 9.0 and 2.3 in 05-06 - as in minutes and fouls - while his weight ballooned to some level over 300 that only the Knicks' medical staff knew for sure. 

Yep, those were the good 'ol days. RIP Isiah. 

2. Erick Dampier 2004 Mavs – 7 yrs/$73 million

Apparently unfazed by the Raef LaFrentz Experience, the Mavs were back at it again two years later, massively overpaying another free agent center. No sooner did they rid themselves of one cap-clogging stiff, they took an obvious Contract Year Bandit off Golden State’s hands, in their seemingly endless quest to pair Dirk with a solid body inside.

Dampier disappointed heavier than his own body became; after notching 12/12 the year before signing, he’d never average double figures in anything other than ‘frustrated glares’ again. 

Of course the irony in all this is that no sooner did the Mavericks finally have their coveted center, and win a title with him, they decided to let him walk. And then traded back for him again. The NBA: Where Amazing Happens.

1. Rashard Lewis 2007 Magic – 6 yrs/$118 million

We’ll give credit where credit’s due: of all the players on this list, Lewis not only played the best through his absurd deal, but helped the Magic climb steadily to a Finals berth in 2009.

That said: $120 million. Actually.

Normally the type of deal reserved for the NBA’s ultra-elite talent, Otis Smith colored outside the lines by offering nine figures to a guy with just a single All-Star appearance on his resume. It was a bold (insane) move by a team with oodles of cap space, only in a summer of very slim free agent pickings.

He'd make the ASG again with the Magic, but never came close to earning the max money thrown his way. Hell, for all we know this deal could've clogged their cap enough to prevent them from actually winning the Finals.

Orlando’s move was widely mocked, and served as a solid foundation for the financial mess that prolonged their Dwightmare a few years later.

Heads shook across the internet last month when reports circled that the Cavs were considering tossing a max-level deal at non-max-level player Gordon Hayward. Faces met palms this past week when the Hornets actually went out and did it. Though the NBA is a Brave New World - with shorter-term contracts and skyrocketing salary caps increasing player movement - even tighter times didn’t prevent GMs from spending money stupidly.

The financial climate used to be a lot shakier, as recently as ten, and even five years ago for some teams. Ratings were down, and franchise values weren’t stratospheric, but players were still being handed predictably dangerous sums of money. It drove the league to a work stoppage when the CBA expired, and it became clear there wasn’t enough to pay everyone.

Along the way, a few GMs made historically idiotic acquisitions that, even then, screamed “impending lockout!” - front offices under the ‘we have to spend our cap space now!’ credo, rolling the dice on new roster additions, and convincing themselves it was money well spent.

Of all the free agents on new teams who’ve failed to live up their billing (and salary), here are the biggest fails:

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