Worst free agency signings in NBA history: 25. Juwan Howard, Washington Bullets
1996. It was the year NBA contracts went bonkers on the free agent front, as both Shaquille O’Neal and Alonzo Mourning had inked seven-year deals upwards of $105 million. After two years with the then-Washington Bullets, the franchise had felt they’d seen enough from Juwan Howard to offer him his own lucrative payday.
Howard had just made the NBA All-Rookie Second Team during the 1994-95 NBA season and All-NBA Third Team during the 1995-96 campaign. He also made an NBA All-Star appearance during the 1995-96 NBA season, while putting up a career-high 22.1 points, 8.1 rebounds and 4.4 assists per game.
However, it looked like he reached his peak after signing the deal. He never made another NBA All-Star appearance in his time in Washington. Although he played and was relatively healthy, he was unable to lead the Bullets to the promised land.
Even when paired with former Michigan Wolverines teammate Chris Webber, Washington only managed to make just one playoff appearance after signing Howard’s deal.
From 1998 to 2000, the newly dubbed Wizards had won a combined 47 games before they decided to move on from Howard. With two years left on his deal, the Wizards shipped him off to the Dallas Mavericks, who after 130 games, shipped him off to the Denver Nuggets where he finished out his deal.
After that, he enjoyed stints with then-Charlotte Bobcats, the Portland Trail Blazers and the Miami Heat before winning a title in his final season in 2012-13 and retiring. Howard finished averaging 18.4 points, 7.4 rebounds, 3.3 assists and 1.0 steals per game as a member of the Bullets/Wizards organization.