If an NBA team planned to sign a player to an illegal contract that could cost them a ton of money and future draft picks, they’d better be sure the player is worth it. That’s a risk you take to bring in a superstar, a franchise-changing player who can make you a title contender. That’s not a risk you take for Joe Smith. But that’s exactly what the Minnesota Timberwolves did before the 1999 lockout-shortened season. For The Win takes a look back at the deal in this week’s edition of Throwback Thursday.

Smith was the No. 1 overall pick of the Golden State Warriors in 1995, after an outstanding college career at Maryland. He stayed in the NBA for 16 years, but played for 13 different teams in that time and never made a single All-Star or All-NBA team. He retired in 2011 with career averages of 10.9 points and 6.4 rebounds a game.

Smith had a promising first three seasons as a pro with the Golden State Warriors, but his production took a hit when he was traded to the Philadelphia 76ers in 1998. After the 1999 NBA lockout, he became a free agent, and was highly sought after. He signed a one-year, $1.75 million deal in Minnesota, well below market value, to allow the team to make other moves that offseason. It was a curious decision to say the least, especially considering he had turned down an $80 million extension with the Warriors prior to being traded, only to find that free agency wasn’t as friendly as he had hoped.

As it turns out, Smith and the Timberwolves had an under-the-table agreement in place, where Smith would sign three one-year deals for very little money, allowing the Timberwolves to acquire his Bird rights, which would allow them to go over the salary cap to re-sign him. He would have then been rewarded with a lucrative contract that would have paid him up to $86 million. This arrangement, of course, was highly illegal, and sanctions came down hard on the Timberwolves when the league found out.

According to J.A. Adande, then of the Los Angeles Times, the entire plan was blown open when agents Eric Fleisher and Andrew Miller parted ways. Miller retained Smith and superstar teammate Kevin Garnett in the split, which prompted a lawsuit that led to the unearthing of many documents, including those detailing the Timberwolves’ illegal agreement with Smith.

Before the start of the 2000 offseason, when Smith had signed the third of his three short-term deals with the Timberwolves for one year and $2.5 million, the league’s investigation of the matter was completed and punishments were handed down.

The Timberwolves were fined $3.5 million, and forfeited their first-round draft picks for the next five years (the team’s 2003 pick was eventually restored). Not only was Smith’s newly-signed contract voided, his previous two were as well, meaning he would no longer retain his Bird rights with the Timberwolves. Additionally, Timberwolves owner Glen Taylor was suspended through August 31, 2001, and VP of basketball operations Kevin McHale took a leave of absence through July 31.

For his part, McHale denied any knowledge of the illegal deal. “I haven’t read a contract in four or five years,” he said at the time. He added that these kinds of arrangements were not uncommon: “There are eight to 10 teams that do this all the time. They’re just good at it. We’re bad.”

McHale was right — not only were the Timberwolves bad at not getting caught, they had awful judgment in players on whom to take this kind of enormous risk.

Smith became an unrestricted free agent and was free to sign with any team, including the Timberwolves. He signed a one-year deal with the Detroit Pistons. The following year, he returned to the Timberwolves for $34 million over six years. He played there for two seasons before being traded to the Milwaukee Bucks. He was traded two more times before the end of that deal, including from the Denver Nuggets back to the Sixers in the Allen Iverson trade.

In four total seasons with the Timberwolves, Smith averaged 10.3 points, 6.3 rebounds and 1.1 assists a game — not terrible numbers by any means, but certainly not the kind of production that would merit all of the trouble the Timberwolves went through to sign him illegally, let alone the hefty fine and lost draft picks that resulted.

Smith’s long but unremarkable playing career was what made this scandal truly inexplicable. If the Timberwolves had had an illegal agreement with Garnett instead, it would have looked stupid if they’d gotten caught, but they’d still have made the gamble on a future Hall-of-Famer and all-time great player. Instead, they essentially threw away a half-decade of future development on a journeyman. The NBA is a strange place sometimes.