1. Joe Smith
Leading up to the start of the 1999 NBA season, a lockout was in place. To give themselves a greater chance in the upcoming shortened season, the Minnesota Timberwolves signed a relatively coveted free agent from the Philadelphia 76ers: Joe Smith.
A high-scoring fourth-year forward from the University of Maryland, Smith’s expected market value for a new contract was around $80 million at the time. So it seemed very bizarre that he agreed to a one-year, $1.75 million deal with the Timberwolves in 1999.
As it turns out, Smith had arranged a private (and very illegal) deal with Minnesota where he would accept one-year deals from them in three consecutive offseasons, which would then allow them to ink him to an extension north of $80 million afterward.
Of course, these transactions did not go unnoticed by the NBA, and as soon as the illegal dealings between the Wolves and Smith were discovered, the league made sure the two parties regretted their decision. The Timberwolves would ultimately lose four first-round draft picks between 2001 and 2005, as well as receive a fine of $3.5 million. As for Smith, all three of his contracts with Minnesota and all his earnings from them were voided.
Overpaying a player or underutilizing resources in your offseason dealings is one thing, but making an illegal agreement of this caliber absolutely takes the cake in terms of sabotaging your franchise. In forfeiting four first-round picks, the Timberwolves lost an unbelievable amount of assets that could have been used to enhance Kevin Garnett’s supporting cast while he was at the top of his game.
To add insult to injury, Joe Smith’s career did not even pan out like one of a superstar worthy of taking this kind of risk for. He became a journeyman, playing for nine different NBA teams after his departure from the Timberwolves.
While we will never know for sure, it is certainly possible that Minnesota threw away their only chance at a championship with Garnett in making their ill-advised deal with Joe Smith. With all these factors considered, there is zero doubt this was the worst free agent signing in Minnesota Timberwolves history.