🏀 NBA’s Most Underrated Contracts: Who Delivered Way More Than They Got Paid For

Welcome to Buckets and Riches — where NBA stars don’t just shoot threes, they stack Gs. From tunnel fits worth mortgages to endorsement empires and crypto hiccups, we break down how basketball’s elite earn it, flex it, and sometimes… brick it. 🏀💸

The latest edition of our newsletter covers:

• Jordan Gave The Bulls a Dynasty For $25M

• Curry Took $44M, Made History

• Pippen Delivered 6 Rings on $18M

• Pistons’ $25M Gamble on Billups

💸Steal Deal Alert

$25M for a Dynasty? Michael Jordan Gave the Bulls a Steal

Michael Jordan, considered the greatest basketball player of all time, won six championships in eight years, six Finals MVPs, five regular-season MVPs, 10 scoring titles, and nine All-Defensive Team selections. Phew! That’s dominance on another level.

Off the court, Jordan’s success may be even greater. His Nike deal turned into a global brand empire. He’s one of the richest athletes ever, and the Air movie? That just underscored his cultural impact.

However, even the most diehard NBA fans don’t realize that although Jordan is worth billions now, he was criminally underpaid during his playing days. Worth $3.8B currently, Jordan only earned $93.87 million during his entire NBA career.

Despite being the best player in the NBA for close to two decades, there were only two seasons when His Airness was the highest-paid player in the league.

Fans today understand better the inner workings of NBA finances than earlier. They are aware of the luxury tax, the second apron, and supermax contracts, among other things. What they should know is that Jordan’s eight-year deal that he signed in 1988 is the best bargain in NBA history.

His eight-year, $25.7 million contract, signed in 1988, stands as arguably the best bargain in NBA history for the team.

In those eight years, Jordan won the NBA Championship four times, became a 4x Finals MVP, and won three of his MVP trophies. In addition, he won six scoring titles, won two steals titles, was named an All-Star six times, had six All-NBA First Team selections, had six All-Defensive First Team selections, and rose to the status of the best player in the world.

For perspective: 2025 No. 1 pick Cooper Flagg signed a four-year, $62.7 million deal before logging a single NBA minute. Draymond Green made $25.9 million last season, more than Jordan earned across four of his six title-chasing seasons.

Jordan was paid commensurate with his ability during his final two years in Chicago, as he signed two separate one-year deals worth over $30 million each. This made him far and away the highest-paid player in the league.

Given that he delivered two more titles to etch the Bulls into the record books as one of the greatest dynasties in sports history, it can be argued that even then, his value far exceeded the compensation he received.

Jordan isn’t just the GOAT. He was the greatest value the league has ever seen.

💸 Moneyball Moments

Jimmy Butler made just $2.1 million in 2014–15, while averaging 20 PPG and winning Most Improved Player.
That was the final year of his rookie deal. The Bulls had a chance to extend him early but waited, forcing themselves to pay max money a year later. Had they locked him up earlier, they would’ve landed a budding superstar for pennies.

💰Maximum Returns

Bulls’ Scottie Pippen Heist: 6 Rings for $18M

Scottie Pippen’s seven-year, $18 million contract, signed in 1991, might be the most one-sided deal in NBA history. It was incredibly valuable for the Chicago Bulls to be severely underpaying one of the best wing defenders in the league at the time. It’s also considered one of the worst contracts in NBA history from a player’s perspective. 

At first, it seemed fair. He was the 16th highest-paid player in the league, and it offered financial security. But as the Bulls kept winning and league revenue exploded, salaries skyrocketed, and Pippen’s didn’t.

By 1995, he was the 74th highest-paid player in the NBA, while putting up All-NBA numbers. Even coach Phil Jackson called the situation “embarrassing.”

It also resulted in the deterioration of Pippen’s relationship with the Bulls, specifically with the team’s GM, Jerry Krause. To this day, Pippen still calls his former GM a “liar” and once verbally assaulted him on the team bus. 

By the end of the contract, Pippen was fed up with the lack of an extension. The relationship with the Bulls front office was beyond repair. He eventually received a 5-year, $67.5 million deal, but was promptly traded to the Houston Rockets after signing the contract.

From 1991 to 1998, Pippen averaged 20 points, 7 rebounds, 6 assists, and 2 steals. He was a 6-time All-Star, a 3-time All-NBA First Team selection, and made 7 All-Defensive First Teams.

Pippen was the perfect Robin to Jordan’s Batman, helping lead the Bulls to six championships in eight seasons.

He didn’t just get underpaid. Pippen got underappreciated until the dynasty was already in the books.

🏀 Gamble That Paid Dividends

Chauncey Billups Signed for $27M, and Delivered a Title

Building a championship-calibre team isn’t an easy feat. Teams such as the 2024-25 Oklahoma City Thunder receive praise for their outstanding depth. But none of that would matter if they didn’t have the main head of the operation in Shai Gilgeous-Alexander. 

The hardest puzzle piece to acquire for any team is the star capable of leading them to the promised land. However, the Detroit Pistons were able to find their prized possession improbably.

After a 50–32 season and a second-round exit in 2002, Detroit had a glaring need at point guard. GM Joe Dumars took a chance on Chauncey Billups. The 6-foot-3 guard played for four teams in his first five seasons, but was fresh off a successful season with the Minnesota Timberwolves. 

The Pistons signed him to a five-year, $27.2 million deal. It quickly became one of the league’s best value contracts.

In his first year, Billups averaged a career-high 16.2 points and led Detroit to its first Eastern Conference Finals appearance since 1991. They were swept by the Nets, but the foundation was set.

In 2003–04, Billups shattered expectations. Not only did the Pistons return to the Conference Finals, but they finished what they sought to do the year before. Their reward: facing the Los Angeles Lakers led by Kobe Bryant and Shaquille O’Neal in the NBA Finals. 

Every analyst predicted the Lakers would destroy the Pistons, but Billups and company had other plans. Detroit went on to win in five games, while Billups won Finals MVP. 

The point guard went on to make two All-Star and All-NBA teams before that initial contract expired. The Pistons eventually rewarded him with a four-year $46.3 million contract afterward.

Billups wasn’t just a good signing. He was the missing piece, at a discount price.

🏀 Shot Clock Back: NBA Stat of the Year

Kawhi Leonard earned just $1.8 million the year he won Finals MVP in 2014.
He was still on his rookie deal while shutting down LeBron James and delivering a title for the Spurs, making him one of the lowest-paid Finals MVPs of the modern era.

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