10) Anfernee “Penny” Hardaway – Signed by the Suns in 1999 for $84 million over 7 years
This was considered a great acquisition at the time as Penny was a two-time all-NBA First Team star. He had one decent season for the Suns, averaging over 16 points, 5 rebounds and 5 assists and was bit by the injury bug soon after. Penny never quite recovered and was shipped to the only team that would take on his inflated contract, the New York Knicks , along with Penny Hardaway for expiring contracts and some young talent that never panned out. While the trade seems one-sided, it gave them the cap space to sign Steve Nash and possibly Joe Johnson if they decide to match an offer made by the Atlanta Hawks .
9) Brian Grant – Signed by the Heat in 2000 for $84 million over 7 years
After averaging a meagre 7.3 points-per-game and 5.5 rebounds-per-game, Brian Grant decided to opt out of his deal with the Portland Trailblazers after being courted by several NBA teams. The result was a three-way trade that sent Shawn Kemp to the Blazers, Clarence Weatherspoon, Chris Gatling, Gary Grant and a first rounder to the Cavaliers and a newly re-signed Brian Grant to the Heat at a price averaging 12 million dollars per season. Strangely, Grant turned down the league maximum $93 million over 7 years that he would have received if he agreed to a trade sending him to the Cavaliers. How a player that averaged such mediocre numbers garnered such interest is beyond anyone’s imagination.
8) Austin Croshere and Jalen Rose – Signed by the Pacers in 2000 for $51 million over 7 years and $93 million over 7 years respectively
While he was not given a ludicrous amount of money, Austin Croshere wasn’t even that good of a player to begin with. Croshere had a strong playoffs outing at the end of the 1999-2000 season and ended up laughing his way to the bank with a contract averaging roughly $7.5 million per season. Croshere would end up relegated to the Pacers bench thereafter and has been pretty much a non-factor in the league. Rose has been a solid player since his signing, but far from being worth a maximum deal. Thankfully for the Pacers, the year after signing Rose, they orchestrated one of the most lopsided trades in recent NBA history, trading him to the Bulls for Ron Artest and Brad Miller.
7) Tim Thomas – Signed by the Bucks in 1999 for $67 million over 6 years
After acquiring Thomas from the 76ers in 1998 for Tyrone Hill, the Bucks saw great promise in the athletic youngster out of Villanova. This resulted in Thomas being a young, heralded free agent who would eventually re-sign with the Bucks for a nearly maximum contract. Unfortunately, Thomas’s attitude in recent years makes it seem like he feels he actually deserved it. Thomas would improve moderately since his signing, but would never live up to potential. He was eventually traded to the Knicks in a 3-way trade along with Nazr Mohammed that sent Keith Van Horn to the Bucks and Michael Doleac to the Hawks.
6) Tariq Abdul-Wahad – Signed by the Nuggets in 2000 for $43 million over 6 years
Considered a blue collar hard worker, Abdul-Wahad (formerly known as Olivier St. Jean) was acquired by the Nuggets in a trade with the Magic and was seen as a strong defensive stopper. The Nuggets gambled and resigned Abdul-Wahad to a six year deal, assuming that he’d be a stronghold for their defense. After one injury plagued season with Denver, Abdul-Wahad was traded in a rebuilding project spearheaded by new Nuggets GM Kiki Vandeweghe sending Abdul-Wahad, Nick Van Exel and young up and comer Raef LaFrentz to the Mavericks for the expiring contracts of Juwan Howard and Tim Hardaway, youngster Donnell Harvey and a first round pick. Abdul-Wahad has played very limited minutes since the trade was made.
5) Michael Stewart – Signed by the Raptors in 1998 for $24 million over 6 years
While this deal wasn’t a make or break move for the Raptors organization, one must keep in mind that Michael Stewart 2.4 blocks-per-game in 21 minutes-per-game for the Kings in his rookie year. Those are insane, Ben Wallace-type block numbers that were unfortunately never even remotely duplicated or anything even close in his future seasons. It is also interesting to note that Stewart was a janitor who tried out for the Kings and made the team. Now the only thing he has to worry about cleaning is his residence on Tiger Woods’ private island.
4) Adonal Foyle – Signed by the Warriors in 2004 for $42 million over 6 years
Speaking of overrated shotblockers, most people were shocked when the salary that Chris Mullin gave Adonal Foyle weighed in at a remarkable average of $7 million per season. Since Foyle has never averaged even 6 points-per-game, that seems like a pretty heavy contract for a guy who can set strong picks and block shots. The past two examples simply go to show that if you can block shots and set picks, you are worth more money in one year than the President of the United States would make if he served 20 straight years in office.
3) Juwan Howard – Signed by the Bullets (Wizards) for $105 million over 7 years
One of the members of the legendary fab-five from Michigan University, Howard has always been a decent scorer, but a mediocre rebounder and defender. Regardless, the team now known as the Wizards felt it was necessary to make Howard a very rich man. Howard was never a great player, but always a quality player and a class act, unfortunately he was never worth anywhere close to what he was paid.
2) Vin Baker – Signed by the Sonics in 1997 for $86.7 million over 6 years
After a career year with the Bucks, becoming the first Bucks player to average 20 points and 10 rebounds since Kareem Abdul-Jabbar did so in the 1974-75 season, Baker was a coveted free agent. What ensued was a three-way trade that sent Shawn Kemp and Sherman Douglas to the Cleveland Cavaliers , Baker to the Sonics and Terrell Brandon and Tyrone Hill to the Bucks. This made many Bucks fans upset, but had they known that after only one good season as Gary Payton’s new running mate in Seattle that Baker would fall off the map and become one of the NBA’s biggest jokes, I’m certain they would not have regretted it.
1) Allan Houston – Signed by the Knicks in 2001 for $100 million over 6 years
Six years later and this is still the ugliest contract in basketball. There’s no question that Allan Houston, when healthy, is one of the league’s finest shooters, but that’s about all he has going for him. Houston is a weak defender and a poor rebounder and has been plagued with injuries in recent years. It would not surprise me if the Knicks cut Houston as part of the new clause in the NBA’s collective bargaining agreement that allows them to cut a solitary player to save money on their luxury tax. If any team needs to utilize this clause, it’s the Knicks. At 34 years old, Houston’s shooting is no longer the commodity that it once was, so it will be interesting to see if he will be able to make a successful NBA comeback.