Cleveland Cavaliers' Shawn Kemp
The worst superstar roster gambles in NBA history include huge contract investments that paid off the least on the basketball court.
As opposed to gambles made by letting a player leave—either via trade or free agency—these risks focus on the decision to acquire a superstar specifically.
The Houston Rockets, similarly, did so by bringing in James Harden and then signing him to an $80 million contract.
While early returns may suggest that the Lakers' investment in Howard isn't paying off quite as well as Houston's is with Harden, these more recent roster gambles are still too early to judge.
We won't truly know for at least a season—or even longer—how those roster moves compare to similar gambles in years past.
What we do know now, however, is that there have been some epically poor decisions made in an attempt to add a superstar name to an NBA franchise's marquee.
This list focuses on players who were considered superstars at the time they were acquired. The second-tier stars, who simply made superstar money, were omitted.
That's why a player like Juwan Howard—the NBA's first to earn $100 million—is not included on this list.
Each roster gamble is listed in chronological order according to the year each player was signed.
Cleveland Cavaliers' Shawn Kemp
The Cleveland Cavaliers acquired five-time All-Star Shawn Kemp from the Seattle SuperSonics in 1997.
In a three-way trade, the Cavs shipped All-Star point guard Terrell Brandon and Tyrone Hill along with a first-round pick in exchange for Kemp along with Sherman Douglas.
In 1996, Kemp led his team to the NBA Finals and was a walking highlight reel during his entire tenure in Seattle.
Kemp's time in Cleveland, however, didn't go as well.
Dealing away Brandon was bad enough for the Cavaliers. To make matters worse, Cleveland then renegotiated Kemp's contract to pay him over $14 million for seven seasons.
He would join the $100 million club of NBA superstars, and Cleveland would live to regret every penny.
At the time, Sports Illustrated's Jackie MacMullan quoted Cavaliers general manager Wayne Embry as saying, "I don't anticipate any problems with Shawn."
But he was wrong.
The former "Reign Man" took the Cavs to the playoffs only once, and famously ballooned way out of shape the year after they got him.
His statistics appear OK in hindsight, but off the court, Kemp proved to be more trouble than he was worth.
He was later traded from Cleveland in 2000, somehow, to the Portland Trail Blazers.
Seattle SuperSonics' Vin Baker
Vin Baker was the other major piece to the Shawn Kemp trade-puzzle of 1997.
Like Kemp, Baker had a great run in the mid-'90s and established himself as a young superstar.
He averaged 21 points and 10 rebounds for the Milwaukee Bucks during the two seasons before he was eventually acquired by the Seattle SuperSonics.
It appeared like a solid play by the Sonics at the time, with the disgruntled Kemp wanting out of Seattle, but history would indicate otherwise.
During five seasons with the Sonics, Baker averaged less than 13 points per game.
The gamble was made even worse by Seattle's decision to ink Baker to a seven-year, $86.6 million contract in 1999.
Eventually, the pain would end for the Sonics after they traded Baker to the Boston Celtics in 2002.
Houston Rockets' Clyde Drexler, Hakeem Olajuwon, Charles Barkley
The Houston Rockets traded Sam Cassell, Robert Horry, Mark Bryant and Chucky Brown to the Phoenix Suns in exchange for Charles Barkley in August of 1996.
The trade came just one year after the Rockets had gone back-to-back as NBA champions from 1994-95.
Barkley joined a superstar-laden roster in Houston that featured teammates Clyde Drexler and Hakeem Olajuwon.
The move was supposed to pay off in the form of NBA championship rings—at least one, maybe more.
The Rockets would never again play for a title, though, as the '90s came to a close.
They inevitably lost a Western Conference finals matchup with the Utah Jazz in six games during Barkley's first season with the Rockets.
The following year, after a slew of injuries, Houston finished only 41-41 before being eliminated by the Jazz again—this time making a first-round exit from the playoffs.
Drexler would retire in 1998. Despite an attempt to replace him with Scottie Pippen, the Rockets were eliminated again in the first round of the 1999 playoffs.
In four games, the Los Angeles Lakers officially closed the book on the late-'90s Rockets for good.
New York Knicks' Allan Houston
Allan Houston averaged 19.3 points in 63 career playoff games.
Sixty of those games were as a member of the New York Knicks, from 1995 to 2001.
When the Knicks advanced to the NBA Finals in '99, Houston led the way with an average of 18.5 PPG.
From 2000-01, he was named to the All-Star team twice.
For a brief moment in NBA history, the player who averaged 17.3 points in 839 regular-season games was considered a superstar.
In that moment, however, the Knicks went all-in on Houston in 2001 and offered him a six-year contract extension worth $100 million.
The deal would make Houston an untradable asset over the life of that contract. Chronic knee issues would also force him to miss all but 70 games from 2003-05, specifically.
During the 2004-05 campaign, Houston's last year in the league, he appeared in only 20 games while averaging 11.9 points. He never played a playoff game in New York after 2001.
Los Angeles Lakers' Shaquille O'Neal, Gary Payton and Kobe Bryant
In July of 2003, the Los Angeles Lakers signed free agents Gary Payton and Karl Malone.
At the time, the Lakers were one season removed from winning three-straight NBA championships.
The events that transpired both on and off the court from there, however, turned this quest for an NBA title into a daytime television soap opera.
This led to tension throughout the organization that only grew larger as Shaquille O'Neal used the media to throw public jabs at Bryant.
O'Neal consistently referred to the Lakers as "his team," suggesting that Malone and Payton came to Los Angeles to play specifically with him.
While blame cannot fairly be pinned on Malone or Payton for the Lakers' issues that year, the roster gamble of adding the two aging superstars to the already volatile mix of O'Neal and Bryant simply did not work.
The Lakers ended up going to the NBA Finals despite all that, but eventually lost to the Detroit Pistons.
The loss, and season, marked the end of the Shaquille O'Neal era in Los Angeles.
New York Knicks' Stephon Marbury
New York schoolboy legend comes home to save the New York Knicks.
I was just as intrigued by that narrative as anyone else when Isiah Thomas first made the move to acquire Stephon Marbury.
The Coney Island product's triumphant return, though, didn't prove to be as glorious.
As a member of the Phoenix Suns, Marbury was averaging 20.8 points prior to Thomas' decision to add him to the Knicks roster in January 2004.
Marbury had just signed a four-year contract extension worth $76 million with the Suns that paid him through 2008-09.
While "Starbury" eventually left New York well-compensated for his services, the roster gamble was a major fail for the Knicks.
In addition to a laundry list of issues off the court, Marbury's production as a player was glaringly worse with every season.
In 2008, his final year with the Knicks, Marbury appeared in only 24 games, averaging a pedestrian 13.9 points per night.
Chicago Bulls' Ben Wallace
I enjoy defense and rebounding as much as the next guy.
Even still, the "Big Ben Era" of Chicago Bulls basketball has always left me scratching my head.
In 2006, for a grand total of $14 million per season, the Bulls used a four-year, $60 million contract offer to lure Wallace away from the Detroit Pistons.
He was 31 years old at the time.
The previous season, Wallace finished among the NBA's top 10 in rebounding, blocks and steals. I suppose that factored into the decision for Chicago.
His production declined in each of those three categories over the next two seasons with the Bulls before Wallace was eventually traded to the Cleveland Cavaliers in 2008.
The 8.8 rebounds he averaged through 50 games with the Bulls in '08 was Wallace's lowest total since the 8.2 he collected with the Orlando Magic in 2000.