Scottie Pippen

Pippen has been married twice and is the father of eight children. He married Karen McCollum in 1988, and the couple had a son, Antron, before divorcing in 1990. Antron passed away in April 2021. Pippen later fathered twin daughters, Taylor and Tyler, with Sonya Roby; Tyler died shortly after birth. He also had a daughter with his former fiancée Yvette De Leon.

In 1997, Pippen married Larsa Younan, who later became a prominent reality television personality on The Real Housewives of Miami. The couple had four children together: Scotty Jr., Preston, Justin, and Sophia. Their eldest son, Scotty Pippen Jr., went on to play in the NBA, while Justin committed to college basketball, and Sophia appeared on Dancing with the Stars: Juniors. Following earlier separation filings, the couple finalized their divorce in late 2021.

After retiring from professional basketball, Pippen discovered that his financial adviser, Robert Lunn, was involved in bank fraud that severely impacted Pippen's investments. Lunn had forged Pippen's signature on a loan to cover personal debts and was subsequently sentenced to three years in federal prison in 2016.

Born in Hamburg, Arkansas, Pippen was the youngest of 12 children in a tall family. While attending Hamburg High School, he played point guard and led his team to the state playoffs, earning all-conference recognition as a senior. Because he stood just 6 feet 1 inch and weighed around 150 pounds upon graduation, he did not receive any college athletic scholarship offers.

He enrolled at the University of Central Arkansas, initially serving as a student manager for the basketball team before earning a roster spot as a walk-on under head coach Don Dyer. During his collegiate career, Pippen underwent a significant growth spurt, eventually reaching 6 feet 8 inches. By his senior season playing in the NAIA, he averaged 23.6 points, 10.0 rebounds, and 4.3 assists per game. His performances earned him consensus NAIA All-American honors in 1986 and 1987, catching the attention of NBA scouts.

Pippen entered the 1987 NBA draft and was selected fifth overall by the Seattle SuperSonics, who immediately traded him to the Chicago Bulls in exchange for Olden Polynice and future draft selections. Playing alongside Michael Jordan and developing within coach Phil Jackson's triangle offense, Pippen blossomed into one of the league's top all-around forwards, earning his first NBA All-Star selection in 1990.

From 1991 to 1993, Pippen helped lead the Bulls to their first three-peat of NBA championships, often defending opposing lead playmakers such as Magic Johnson during the 1991 NBA Finals. When Jordan briefly retired prior to the 1993-94 season, Pippen took over as Chicago's primary leader, winning the 1994 NBA All-Star Game MVP award and finishing third in league MVP voting. In the 1994-95 campaign, he led the Bulls in all five major statistical categories (points, rebounds, assists, steals, and blocks).

Following Jordan's return and the acquisition of Dennis Rodman, Pippen and the Bulls mounted a second three-peat from 1996 to 1998. The 1995-96 team set a then-record regular season mark of 72 wins and 10 losses before capturing the title. During the 1997 NBA Finals against the Utah Jazz, Pippen famously psyched out Karl Malone at the free-throw line in Game 1 and made a key defensive deflection in Game 6 to secure Chicago's fifth championship. He completed the second three-peat in 1998, leaving Chicago as the franchise's second all-time leader in points, assists, and steals.

In January 1999, Pippen was sent to the Houston Rockets in a sign-and-trade deal, teaming up with Hakeem Olajuwon and Charles Barkley during the lockout-shortened season. Despite averaging 40.2 minutes per game and earning an eighth selection to the NBA All-Defensive First Team, on-court friction with Barkley developed, and the Rockets suffered a first-round playoff exit.

Pippen was traded to the Portland Trail Blazers ahead of the 1999-2000 season. Serving as the starting small forward on a deep squad featuring Rasheed Wallace and Steve Smith, he helped guide Portland to a 59-23 record and a trip to the Western Conference Finals against the Los Angeles Lakers. Pippen spent four seasons in Portland, qualifying for the postseason in each campaign before departing after the 2002-03 season.

Pippen returned to the Chicago Bulls for the 2003-04 season, signing a two-year contract intended to provide veteran leadership for a young roster. Due to recurring injuries, he was limited to 23 games, playing his final NBA game in February 2004. He officially announced his retirement from the NBA on October 5, 2004.

In early 2008, at age 42, Pippen returned to competitive basketball for a brief European tour. He played two games in Finland for Torpan Pojat (ToPo) and one game in Sweden for the Sundsvall Dragons, later praising the quality of basketball talent in Scandinavia.

Pippen represented the United States national team in international competition, compiling a perfect 22-0 record in USA Basketball competition. In 1992, he was selected to the iconic United States Olympic "Dream Team," which swept through the Tournament of the Americas and captured the gold medal at the 1992 Summer Olympics in Barcelona by an average margin of 44 points per game.

He returned to Olympic competition for the 1996 Summer Olympics in Atlanta, helping lead the team to another undefeated run and a second gold medal. By winning titles in 1992 and 1996, Pippen became the first basketball player in history to win an NBA championship and an Olympic gold medal in the same calendar year twice.

Recognized for his defensive instincts, court vision, and 88-inch wingspan, Pippen was widely regarded by Phil Jackson as a versatile defensive asset capable of guarding every position on the court. He amassed 10 total NBA All-Defensive Team selections and led the league in steals during the 1994-95 season. He also ranks near the top of NBA playoff history in career steals.

The Chicago Bulls retired Pippen's number 33 jersey in December 2005, making him one of only a few players to receive the honor from the franchise. In 2010, he was inducted into the Naismith Memorial Basketball Hall of Fame twice on the same day, once for his individual playing career and once as a member of the 1992 Dream Team. In 2011, the Bulls unveiled a bronze statue of Pippen inside the United Center, and in 2021, he was named to the NBA 75th Anniversary Team.