Legendary basketball player Scottie Pippen won six NBA championships with the Chicago Bulls and has two Olympic gold medals under his belt. His journey to becoming one of the team’s top superstars was paved with dedication, incredible teamwork, and relentless perseverance, as reported by ichicago.net.
A Tough Childhood and a Passion for Basketball

The future Chicago Bulls forward was born on September 25, 1965, in Hamburg, Arkansas. He grew up in a large family as one of twelve children. His father, Preston Pippen, worked tirelessly at a local paper mill to provide for the family. However, sending the kids to college was simply out of the question financially.
Adding to their struggles, Scottie’s older brother suffered a severe injury during a high school gym class that left him paralyzed. This tragedy deeply affected the entire family. Just a few years later, Preston Pippen suffered a devastating stroke. The illness left him unable to walk on his own, paralyzing the right side of his body.
Despite these family hardships, Scottie found an escape in basketball. He started playing for Hamburg High School, where the talented guard led his team to the state playoffs and earned MVP honors. Surprisingly, despite his success on the court, he didn’t receive a single college scholarship offer.
College Basketball and the Start of a Pro Career

Fate finally smiled on Pippen when he caught the eye of the head basketball coach at the University of Central Arkansas. This marked the beginning of his collegiate playing career.
During his time in college, Pippen experienced a massive growth spurt, shooting up from 6’1″ to 6’8″. He quickly became the team’s standout player, naturally drawing the attention of NBA scouts. In the 1987 NBA Draft, Pippen was selected by the Seattle SuperSonics but was quickly traded to the Chicago Bulls.
The rookie made his NBA debut on November 7, 1987, in a matchup against the Philadelphia 76ers. The Bulls secured a victory, and Pippen finished his very first game with a solid 10 points and 4 assists.
Pippen possessed a unique skill set that helped him carve out a regular spot in the Bulls’ rotation right from his rookie season. His impressive height and physical strength allowed him to maneuver effectively in the paint and finish at the rim.
The Dynamic Duo: Michael Jordan and Scottie Pippen

When Pippen joined the Bulls, the undisputed star of the franchise was Michael Jordan. It didn’t take long for the newcomer’s elite play to earn him a spot in the 1990 NBA All-Star Game. From 1991 to 1993, he established himself as a cornerstone of the Bulls’ championship runs.
On the court, Pippen and Jordan complemented each other perfectly, a synergy that translated into countless wins for Chicago. While Jordan took control of the scoring, Pippen was always right there, locking down opponents and racking up steals.
Pippen anchored the team whenever Jordan needed a breather. While the forward didn’t always dominate the stat sheet, he was undeniably the second most valuable player on the Bulls roster.
“He was the perfect complement to Michael. Michael was tough. You had to be ready for his criticism every single day. Scottie would put his arm around you and make sure you were doing okay. He’s a kind soul,” former Bulls point guard Steve Kerr once shared in an interview about his teammate.
After Jordan retired for the first time, Pippen stepped into the role of the team’s undisputed leader. He earned All-NBA First Team honors during the 1993-1994 season. However, his stellar year was marred by a controversial moment during a crucial playoff game. With just seconds left on the clock, Pippen refused to sub back into the game after head coach Phil Jackson drew up the final play for another player instead of him.
The forward made the All-NBA First Team once again in the 1994-1995 season. Jordan’s legendary return, combined with the fierce dynamic between Dennis Rodman and Pippen, ultimately propelled the Bulls to a historic three-peat, winning consecutive championships from 1996 to 1998.
Olympic Gold

Competing in the 1992 and 1996 Olympic Games stands out as a major highlight in Pippen’s basketball career. He was a key figure for Team USA, representing his country with pride and dominance on the international stage.
The US squad that competed in the 1992 Summer Olympics famously became known as the “Dream Team.” It marked the first time in history that active NBA players were allowed to participate. Pippen shared the court with basketball royalty, teaming up with legends like Michael Jordan, Larry Bird, and Magic Johnson.
While he may not have been the primary face of the team, Pippen provided elite, lockdown defense against international opponents and expertly spaced the floor for his teammates. The result was absolute domination, with Team USA sweeping the competition and solidifying America’s supremacy in global basketball.
By the time the 1996 Summer Olympics rolled around, Pippen was competing as an established NBA superstar. Team USA boasted another powerhouse roster, featuring names like Karl Malone, Shaquille O’Neal, Hakeem Olajuwon, Michael Jordan, and others. Pippen was a relentless defensive force during the tournament and expertly orchestrated the team’s offense.
The US National Team captured the gold medal once again. Working alongside Michael Jordan, Pippen helped lead the team to ultimate international glory twice.
The Houston Rockets and Portland Trail Blazers Era

After Jordan retired for the second time, the Chicago Bulls front office began a massive rebuild. During the ensuing roster shakeup, Pippen was traded to the Houston Rockets in 1998.
The coaches envisioned the forward forming a superteam alongside Charles Barkley and Hakeem Olajuwon to make another title run. However, Pippen repeatedly clashed with Barkley. To make matters worse, he was playing the small forward position in a system that led to visible frustration for the star.
The Rockets managed to reach the playoffs but were bounced in the very first round. After spending just one turbulent season in Houston, Pippen moved on to the Portland Trail Blazers.
The change of scenery did him well, and the forward found himself in a much better situation. Pippen stepped up as a primary leader and playmaker for the Trail Blazers. He actively mentored the team’s younger players, sharing his championship experience.
Even in the later stages of his career, Pippen remained an elite defender and a highly respected locker room leader. The 1999-2000 season was particularly memorable. The Trail Blazers were just one step away from reaching the NBA Finals but ultimately suffered a heartbreaking loss to the Los Angeles Lakers.
In a fitting full-circle moment, Pippen signed a contract to return to the Chicago Bulls for the 2003-2004 season. He suited up for 23 games during his farewell tour before officially retiring from professional basketball in 2004.
Life After Professional Basketball
Pippen took on an advisory role with his beloved Chicago Bulls. His main focus was passing down his invaluable experience to the next generation of players and weighing in on front-office decisions. The former Bulls legend has also made frequent television appearances as an expert analyst and color commentator for NBA games.
In 2021, Pippen released his highly anticipated autobiography, Unguarded. In the memoir, the author opens up to readers about the defining moments of his career, his struggles with financial difficulties, and his complicated relationship with former teammate Michael Jordan.
Throughout his illustrious career, Scottie Pippen racked up numerous prestigious accolades, including:
- being named one of the 50 Greatest Players in NBA History;
- winning USA Basketball Male Athlete of the Year twice—first in 1992 with the Olympic team, and again in 1996 representing the Chicago Bulls;
- being inducted into the Naismith Memorial Basketball Hall of Fame twice in 2010;
- becoming a unique player who won an NBA Championship and an Olympic gold medal in the exact same year;
- being selected to the NBA All-Time Team in honor of the league’s 50th anniversary.