The tragic real-life story of Scottie Pippen

When Scottie Pippen retired from the NBA in October 2004, it concluded one of the greatest and most accomplished careers in the history of professional basketball. During his prime years in the 1990s as a member of the Chicago Bulls, Pippen helped lead the Bulls to six championships, winning three straight between 1991-93 and 1996-98, as well as winning two Olympic gold medals in 1992 and 1996. He was named one of the 50 greatest players during his career and was elected to the Hall of Fame in his first year of eligibility. Partnered with Michael Jordan, the pair formed one of the greatest dynamic duos in professional sports. 

As a player, Scottie Pippen made his mark on the defensive side of the basketball. Usually asked to guard the opposing team's best wing players, Pippen's athleticism and intelligence stifled opponents day in and out and turned Chicago into one of the best defensive teams of all-time. This ability led to Pippen being named to the All-Defensive team every year between 1991 and 2000. While Jordan led the team each year in scoring, Pippen followed him in points and developed a total offensive game, becoming a great distributor and rebounder. 

Despite all the success and accolades, he earned during and after his career, Scottie Pippen's life has been far from easy. Here is the tragic real-life story of Scottie Pippen.

Scottie Pippen grew up poor, one of 12 children

Scottie Pippen was born Scotty Maurice Pippen, the youngest of a dozen children to Preston, a paper mill factory worker, and Ethel Pippen on September 25, 1965, in Hamburg, Arkansas. Pippen's childhood home was a two-room house, and the town he lived in had only a population of around 3,500 people. Both his parents were tall (his mother was 6 feet), and while Pippen would eventually become the tallest member in his family, during his adolescent and teenage years, he was still the runt of the litter on the basketball court where he and his siblings spent their days.

During Scottie's freshman year at Hamburg High School, he and the rest of his family took a big hit when his father suffered a stroke that placed him in a wheelchair for the rest of his life, according to the Chicago Tribune. The family struggled financially before the stroke and could not afford to send any of their children to university. It seemed like Scottie's only shot at college might be through an athletic scholarship, and he threw himself into sports.

Scottie Pippen struggled for playing time in high school

Entering high school, Scottie Pippen stood barely over 6 feet and around 135 pounds. Not long after his father's stroke, Pippen's older brother, Ronnie, became wheelchair-bound as well from an accident. The fear of injury haunted Pippen, as he told Chicago Tribune sportswriter Sam Smith during his career: "I've always thought that one injury could wipe all of this away. I'm able to run and jump and do all the things I can do. I'm blessed. ... But I always would look at (the late) Darryl Stingley [an NFL player who was left quadriplegic at the age of 26]. I'd kind of watch him sometimes and see my brother, a healthy, strong young man, and all of a sudden he's confined to a wheelchair, to where he can't get around. I think about that a lot."

Pippen made varsity as a sophomore but would spend the next two years fighting to find playing time. It wasn't until his senior year that he finally made the starting lineup as the point guard. Scottie led his team to the regionals but did not spark interest from any universities. His high school coach called in a favor to a friend, the University of Central Arkansas in Conway basketball coach Don Dyer and Pippen was offered a Basic Education Opportunity Grant and joined the NAIA basketball team ... officially listed as the team manager, although he says he didn't do much in that role.

Scottie Pippen was a rising star in college

Though Scottie Pippen was in school and part of the basketball program at Central Arkansas, he was not on the team. Coach Dyer felt the freshman needed to build up his upper body and planned to keep Pippen as the team manager for his first year. But after multiple players left the team, Pippen took advantage of the open spots.

Scottie Pippen joined the team as a freshman and averaged 4.3 points per game. Remarkably, the 6'1 Pippen grew 5 inches before his sophomore season and began to develop his upper body strength as Dyer had instructed. Combining his new body with the experience as a ball-handler and distributor during his time as the point guard, Pippen became the best player on the roster his sophomore year, averaging 18.5 points and 9.2 rebounds per game. His numbers only grew his next two years, as did his height to a 6'8 frame.

Entering the 1987 NBA Draft, the Chicago Bulls saw Scottie Pippen as a talented prospect for their team but feared he would be gone by their pick at No. 8. Bulls' general manager Jerry Krause was building in the process of building a team with players that could complement the Bulls' young superstar, Michael Jordan. So they had the Seattle Supersonics agree to draft Scottie Pippen at No. 5 and then trade him to Chicago for the Bulls' No. 8 pick and multiple draft picks over the next two seasons.

Scottie Pippen had relationship problems

In 1987, Scottie Pippen and his girlfriend, Karen McCollum, had their first child, a boy named Antron. The next year, the couple got married. (Antron would eventually follow his father in basketball, becoming one of the top high school prospects in Georgia and playing college basketball at Texas A&M International, though he did not follow his father to the NBA.) The marriage between Karen and Scottie lasted only two years and ended in divorce in 1990. At the same time, according to documents obtained by The Blast, Pippen was involved with another woman named Chyvette Valentine, who sued him in 2019 for the maximum amount in small claims court for expenses she incurred during their relationship between 1987 and 1993.

According to Valentine, she did not become aware of Pippen's wife and child until Valentine's Day in 1988 when he told her while they were together in bed. She recalled one time finding baby items in his house — she says Pippen told her it was for his sister's child. Valentine claims that while she was with Scottie Pippen, she paid for hotels, gas, and other expenses he said he would pay but never did. And he almost certainly could have paid; in August 1987, Scottie Pippen signed his rookie contract with the Bulls and quickly became a millionaire.

Scottie Pippen's early career and losing to the Bad Boy Pistons

The professional version of Scottie Pippen, a 6'8 small forward with a high motor, athleticism, and defensive skills, became the perfect complement to his dynamic scoring teammate, Michael Jordan. Along with Pippen, the Bulls also drafted power forward Horace Grant from Clemson University. The trio formed the foundation for their championship teams in the early 1990s.

By his third year with the Bulls, Scottie Pippen made his first All-Star team and the team promoted assistant coach Phil Jackson to head coach. By this time, the Bulls' squad routinely found themselves in the postseason. However, playoff success and trips to the NBA Finals were snuffed by the Detroit Pistons for three straight years. The "Bad Boy Pistons" were known for their aggressive style of defense, a style that often left Jordan and Pippen (the Bulls' primary scorers) bruised on the court. Detroit was led by Isiah Thomas (left) and Hall of Fame coach Chuck Daly (right). The Bulls fell to Detroit in the 1988 and '89 postseasons. In 1990, with the recent death of his father in the back of Scottie Pippen's mind, he and Jordan led the Bulls to another best of seven series with the Detroit Pistons. In the decisive Game 7 of the Eastern Conference Finals against Detroit, Pippen had one of his worst games as he struggled with a migraine headache in a losing effort. The "Migraine Game" led many to question Pippen's toughness and dedication to winning a championship.

Scottie Pippen finally won a championship but signed a bad contract

In 1991, Scottie Pippen and the Bulls finally broke the Pistons' stranglehold on the Eastern Conference in a four-game sweep and found themselves in the NBA Finals against the Magic Johnson-led Los Angeles Lakers. Los Angeles had won five NBA championships during the 1980s and was seen as the veteran team by comparison to the young Bulls making their first trip to the NBA Finals. After losing the first game in Chicago, Pippen ended up guarding Magic Johnson, desperate to slow down the Lakers' offense and tempo. Scottie Pippen's size and speed matched up well against Johnson, possibly the biggest point guard in the league at 6'9 and 215 pounds. The strategy proved to be effective.  Pippen's defense on Johnson limited the offensive efficiency of Magic and the entire Lakers squad. With Scottie Pippen manning the defensive front and Michael Jordan free to score, the Bulls won four straight games and their first of six championships in the decade.

With his contract expiring, Pippen decided that his next contract would be longer than the four-year deal he started out with when he entered the league. In order to ensure his family's future and protect himself from injuries like his family members, Scottie Pippen signed a five-year, $18 million deal two weeks after the championship. The decision would haunt him the rest of the decade.

Scottie and the Bulls completed the three-peat, lost Jordan

On the basketball court, the next two years would be some of the best of Scottie Pippen's career. In 1992 and '93, the Bulls won two more championships, becoming the first team to win three straight championships since the Boston Celtics won eight straight titles from 1959-1966. Following the 1992 NBA season, Pippen was a member of the first US Olympic Basketball team to feature professional players. Nicknamed the Dream Team, the squad easily took home the gold medal in Barcelona and marked a turning point for the NBA and basketball internationally. Future NBA superstar and German native Dirk Nowitzki called Pippen his favorite player growing up.

After the 1993 season and another championship, the Bulls were shocked when their star player, Michael Jordan retired from basketball to play baseball. Scottie Pippen became the clear top player on the Bulls and further established his superstar status. In February, he was awarded the All-Star Game MVP after leading the East to a victory. The Bulls found themselves back in the postseason. However, during a series against the New York Knicks, Pippen infamously refused to enter the final moments of Game 3 when coach Phil Jackson drew up a play for another player. The Bulls still won the game, and Pippen was confronted by teammates in the locker room. Though the situation cooled, the Bulls fell to New York and missed the Finals for the first time in three seasons.

More children, more legal issues, more winning

Scottie Pippen struggled in his personal life between 1994 and 1995, and he was arrested twice in a year and a half on charges of gun possession (eventually dropped) and battery. His fiancee at the time, Yvette Deleone, said he had grabbed and pushed her in their home, according to the LA Times. During this period, Deleone and another woman took Pippen to court to force him to pay alimony and recognize two of his children, Taylor and Sierra Pippen

On the court, Michael Jordan eventually returned to the Bulls, and Horace Grant, who had left for the Orlando Magic, was replaced with Dennis Rodman. Rodman had been an enforcer on the Bad Boy Pistons teams in the late '80s that beat (and beat up) Pippen and the Bulls. He was also the game's best rebounder and a perfect replacement. In their first season together in 1996, the Bulls set a record with 72 regular-season victories and won their first championship since 1993. That summer, Pippen won his second Olympic gold medal as a part of the 1996 men's basketball team. The Bulls won two more titles in '97 and '98, completing their second three-peat of the decade and cementing themselves as one of the greatest teams in sports history.

In 1997, to commemorate the 50th NBA season, the league put together a list of the 50 greatest players in the game's history, and named Scottie Pippen one of the 50 greatest players. That same year, Pippen married his second wife, Larsa Younan.

Scottie Pippen finally left the Chicago Bulls

Scottie Pippen helped the Bulls complete their second three-peat in 1998. However, the contract he signed back in 1991 had finally come back to bite him. A year after signing the contract, Pippen was the second highest paid player on the Bulls (behind only Jordan) and the 16th highest paid in the league. By the 1998 season, despite still being the clear No. 2 player on the team after Jordan, Scottie Pippen was the sixth highest paid player on the team and the 122nd highest paid player in the league. Bulls management had refused to renegotiate the contract despite Pippen voicing disapproval throughout the decade, going so far as saying publicly he would not play for the Bulls while recovering from a foot injury prior to the 1997-1998 NBA season. Scottie Pippen's name was also constantly in trade rumors throughout the 1990s, most famously after winning his fifth title. During the '96-'97 offseason, Bulls' general manager Jerry Krause attempted to trade Pippen to the Toronto Raptors for the rights to high school prospect Tracy McGrady (above). According to McGrady, he was flown out to Chicago for a workout in secret, but Michael Jordan himself "called and axed the whole deal."

Scottie Pippen made sure he was finally compensated for what he felt he deserved. On January 22, 1999, Scottie Pippen and the Bulls agreed to a sign and trade with the Houston Rockets. He signed a five-year, $67.2 million deal with the Bulls and was immediately traded to the Houston Rockets.

Scottie Pippen had problems in Houston and Portland

In his one season with the Rockets, Pippen struggled to adjust to the new system with veterans and Olympic teammates Hakeem Olajuwon and Charles Barkley. He also feuded with Barkley and was arrested on DUI suspicion in the winter. Statistically, Pippen's shooting percentage was the worst in his career. The Rockets were knocked out of the postseason in the first round by the Los Angeles Lakers, led by Shaquille O'Neal and Kobe Bryant.

No longer desiring to play with Barkley and feeling that the team was no longer good enough for a championship run, Pippen demanded a trade from Houston. Before the 1999-2000 season, Scottie Pippen was traded to the Portland Trail Blazers. In his first season, the Blazers were on the precipice of making the NBA Finals but blew a large lead in the final minutes of the fourth quarter against the Lakers, again led by Shaq and Kobe, plus former Bulls coach Phil Jackson in his first season with L.A. The most memorable play of the series was probably Kobe Bryant crossing over and dribbling past Pippen and tossing an alley-oop to Shaq to put the nail in the coffin. The Lakers would win the NBA Finals (their first of three straight), and Scottie Pippen would not get as close to a championship for the rest of his career.

Scottie Pippen retires and post-retirement life

In 2003, Scottie Pippen signed a contract to return to Chicago as a veteran presence, but retired at the end of the season after a poor showing. Today, he works as a commentator for ESPN's basketball program "The Jump." In 2014, Pippen's financial advisor was sentenced to three years in prison for multiple counts of bank fraud. Pippen had invested around $20 million with the advisor but was only able to recoup $8 million. 

Pippen had four children with wife Larsa, above, but Scottie filed for divorce in 2016, saying she had been unfaithful to him. Pippen made more headlines in 2020 after participating in "The Last Dance," a documentary about the Chicago Bulls' dynasty during the 1990s. Pippen was reportedly unhappy with how he was portrayed and unhappy with comments Michael Jordan made about him. Dennis Rodman and others came to Pippen's defense, but time will tell if the No. 1 and No. 2 can ever work it out.