Scottie Pippen played in the NBA from 1987-88 to 2003-04. He built the majority of his Hall of Fame career with the Chicago Bulls before he had stops in Houston and Portland. “Pip” had a sentimental return to Chicago for his last year in the league before retiring.Pippen closed his career in pro basketball with $109.9 million in salary earnings. In 2023, he is reportedly worth $20 million.Paul Guarino@PCG7Scottie Pippen actually made more money ON THE COURT in his career than Michael Jordan (but he also played more seasons than MJ).Pippen's career earning: $109,192,430Jordan's career earning: $93,285,000#TheLastDance15880Scottie Pippen actually made more money ON THE COURT in his career than Michael Jordan (but he also played more seasons than MJ).Pippen's career earning: $109,192,430Jordan's career earning: $93,285,000#TheLastDance https://t.co/jvoR2cIq9fAfter his retirement, the six-time NBA champ reportedly suffered huge financial losses due to bad investments. A big part of his money also went to child support. Pippen has eight kids with four different women.Some analysts have said over the years that Scottie Pippen was never a smart businessman. He played 13 seasons for the Chicago Bulls but only earned $32.6 million. From 1991-1997, Chicago had him in the books for $19.5 million. During that span, he averaged $2.7 million annually.Years later, Pippen opened up on his reasoning behind the unreasonable contract he signed with the Bulls. “Pip” came from a poor family and wanted to secure those close to him. Pippen’s father and brother were wheelchair-bound, which only pushed him to sign the contract.Fortunately, one year in Houston and four years in Portland helped make up for his career earnings. The Rockets paid him $11 million for one season while the Blazers improved his finances with $66 million for four years.Spotrac@spotracTechnically speaking, Scottie Pippen signed every contract of his career with the Chicago #Bulls. His 5 year $67M extension in 1999 was a sign-&-trade to the #Rockets. Cash Earned Per Team#Blazers: $66.3M#Bulls: $32.6M#Rockets: $11Mbit.ly/2Vr2TOx2711Technically speaking, Scottie Pippen signed every contract of his career with the Chicago #Bulls. His 5 year $67M extension in 1999 was a sign-&-trade to the #Rockets. Cash Earned Per Team#Blazers: $66.3M#Bulls: $32.6M#Rockets: $11Mbit.ly/2Vr2TOxThe Chicago Bulls made amends at the tail-end of his career after signing "Pip" to a two-year $10 million deal. Michael Jordan’s longtime teammate played just one season before he was waived by agreement.Scottie Pippen would have easily commanded millions in today’s NBAScottie Pippen’s resume, despite being incredibly impressive, is still sometimes overlooked. At the peak of his career, he was arguably the top small forward in the NBA. When Michael Jordan left to play baseball, Pippen carried the Chicago Bulls.Despite taking on the double and triple-teams that Jordan left behind, he managed to show his worth to the fans and franchise. He led the Bulls in almost every statistical category and very nearly dragged them to the Eastern Conference Finals.Boardroom@boardroom2) Decades away from their dominance and years after The Last Dance debuted, it was Scottie Pippen who outsold the majority of today’s NBA elite. Having the second most popular jersey this summer, he outsold Michael Jordan - No. 5 on the list - and Dennis Rodman (No. 10).112) Decades away from their dominance and years after The Last Dance debuted, it was Scottie Pippen who outsold the majority of today’s NBA elite. Having the second most popular jersey this summer, he outsold Michael Jordan - No. 5 on the list - and Dennis Rodman (No. 10). https://t.co/xHfN32xDJJGiven his skills and his accomplishments, Pippen would easily command at least $40 million per season. Some of today’s NBA players don’t have half of what he can bring to the table and yet they’re remarkably highly valued.Scottie Pippen played in the late ‘80s, ‘90s and early 2000s. His game would be tailor-made with the way the game is played over the last decade or so. Teams would line up for his services and companies would be looking to offer him to endorse their products.Also read: “Once Michael got Scottie Pippen, it was a wrap” – Dennis Rodman recalls giving 6 stitches to 6X NBA champion