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On January 29, 2020, he made his return to the NBA, 371 days after being injured. Coming off the bench for the Pacers, he scored 9 points in 21 minutes of playing time, including a game-tying three-pointer, in an overtime win over the Chicago Bulls. After the game, an emotional Oladipo dedicated the shot to Kobe Bryant and eight other lives lost in a California helicopter crash, three days prior.

Oladipo was born in Silver Spring, Maryland, and raised in Upper Marlboro, Maryland. His mother, Joan Amanze Oladipo, is a nurse and Nigerian immigrant, while his father, Christopher Oladipo, a native of Blama, Sierra Leone, is also of Yoruba Nigerian descent. Oladipo’s father is a public health executive for Prince George's County, Maryland with a Ph.D in behavioral science from the University of Maryland, College Park. Oladipo's parents married in the United States in 1985. Oladipo has three sisters, Kristine (1986), Kendra (1990), who became deaf in second grade, and twin sister Victoria.

On November 12, 2019, the Indiana Pacers announced that they had assigned Oladipo to the Fort Wayne Mad Ants while waiting for his knee to heal; he was recalled to the Pacers the same day, following practice with the Mad Ants.

On November 3, 2018, Oladipo's 3-pointer with 3.4 seconds remaining gave Indiana a 102–101 comeback victory over the Boston Celtics, as he finished with 24 points and 12 rebounds. On November 17, against the Atlanta Hawks, Oladipo left the game in the first quarter with a right knee injury. He missed 11 games with the injury, returning to action on December 12. On January 4, he scored 36 points and made a 3-pointer from just above the top of the arc with 0.3 seconds left in overtime to lift the Pacers to a 119–116 win over the Chicago Bulls. On January 23 against the Toronto Raptors, Oladipo suffered from a ruptured quad tendon in his right knee, which ruled him out for the rest of the season. He underwent successful surgery five days later. Despite the injury-riddled season, Oladipo was selected as an Eastern Conference All-Star reserve.

Oladipo is also a singer, having released an EP, Songs for You in 2017 and his debut album V.O. in 2018. He also appeared as the Thingamajig on season 2 of The Masked Singer, finishing in 5th.

On July 6, 2017, Oladipo was traded, along with Domantas Sabonis, to the Indiana Pacers in exchange for Paul George. In his debut for the Pacers in their season opener on October 18, Oladipo had 22 points, five rebounds, four steals and four assists in a 140–131 win over the Brooklyn Nets. On October 25, he scored a game-high 35 points on 11 for 18 shooting in a 114–96 loss to his former team, the Oklahoma City Thunder. On October 29, he had 23 points and five assists and knocked down a step-back 3-pointer with 10 seconds left to propel Indiana a 97–94 victory over the San Antonio Spurs. He was subsequently named Eastern Conference Player of the Week for games played October 23–29. On December 10, he had a career-high 47 points and added seven rebounds and six assists to lead the Pacers to a 126–116 overtime win over the Denver Nuggets. He was subsequently named Eastern Conference Player of the Week for games played December 4–10. On January 23, 2018, he was named an Eastern Conference All-Star reserve. On March 23, in a 109–104 win over the Los Angeles Clippers, Oladipo extended his streak of games with at least one steal to 56 games, breaking a tie with Chris Paul and Gary Payton for the sixth-longest such streak in NBA history.

On June 25, Oladipo was named the NBA Most Improved Player for the 2017–18 season. Oladipo averaged 23.1 points per game (ninth in the NBA), 5.2 rebounds, 4.3 assists and led the NBA in steals at 2.4 per game. He set career highs in nearly every statistical category. Also in 2018, Oladipo was named to the NBA All-Defensive First Team.

On June 23, 2016, Oladipo was traded, along with Ersan İlyasova and the draft rights to Domantas Sabonis, to the Oklahoma City Thunder in exchange for Serge Ibaka. He made his debut for the Thunder in their season opener on October 26, scoring 10 points in 26 minutes as a starter in a 103–97 win over the Philadelphia 76ers. On October 31, he signed a four-year, $84 million contract extension with the Thunder. A right wrist injury in mid-December forced Oladipo to miss nine straight games. He returned to action on December 31 and scored 15 points against the Los Angeles Clippers. On March 7, 2017, Oladipo returned to the starting lineup after missing six games with back spasms and scored 16 points in a 126–121 loss to Portland.

During the 2015 NBA All-Star Weekend, Oladipo competed in the Rising Stars Challenge and the Slam Dunk Contest, finishing second in the dunk contest behind Zach LaVine.

On March 4, 2015, Oladipo scored a career-high 38 points on 15-of-25 shooting in a loss to the Phoenix Suns.

On October 25, 2015, the Magic exercised their fourth-year team option on Oladipo's rookie scale contract, extending the contract through the 2016–17 season. Five days later, he recorded his second career triple-double with 21 points, 13 rebounds and 10 assists in a double-overtime loss to the Oklahoma City Thunder. He also hit a buzzer-beating three-pointer to send the game into double overtime. Oladipo averaged just 12.8 points per game over his first 12 games of the season. Head coach Scott Skiles moved Oladipo to a bench role for the Magic's November 25 game against the New York Knicks. Oladipo continued coming off the bench following this performance, averaging 17.0 points, 5.4 rebounds, 4.5 assists, 1.0 steals and 1.4 blocks over his first eight games off the bench. On January 4, he started for the Magic for the first time since November 23. In 34 minutes of action, he recorded a team-high 18 points, 7 rebounds, 5 assists and 2 steals in a loss to the Detroit Pistons. On March 18, he scored a career-high 45 points in a 109–103 loss to the Cleveland Cavaliers, becoming the ninth player in franchise history score 40 and the first Magic player to do so since Arron Afflalo in December 2013. Oladipo missed the final three games of the season with a concussion.

On October 24, 2014, Oladipo was ruled out indefinitely after suffering a facial fracture in practice the previous day. Two days later, the Magic exercised their third-year team option on Oladipo's rookie scale contract, extending the contract through the 2015–16 season. He made his return from injury on November 14 wearing a facial protection mask as he made his season debut against the Milwaukee Bucks. In 25 minutes off the bench, he recorded 13 points, 3 rebounds and 2 assists in a 101–85 win. On January 12, he recorded 33 points against the Chicago Bulls and two days later recorded 32 points against the Houston Rockets to record his first career back-to-back 30-point games.

After playing CYO basketball at St. Jerome Academy in Hyattsville, Maryland, Oladipo played high school basketball at DeMatha High School, also in Hyattsville. As a senior, he averaged 11.9 points, 10.3 rebounds and 3.6 blocks per game. He led DeMatha to a 32–4 record and the Washington Catholic Athletic Conference and City championships. Oladipo was named to the Washington Post 2010 All-Met First Team and the First Team All-WCAC. He was ranked No. 144 overall and the No. 41 shooting guard in his class by Rivals.com, while Scout.com listed him as the No. 39 shooting guard in his class, and ESPN listed him at No. 53 at his position.

On April 9, 2013, at a press conference with Tom Crean, Oladipo announced his decision to forgo his senior season at Indiana and enter the 2013 NBA draft. He was projected as a top-15 pick by ESPN and CBS Sports. Oladipo was invited to sit in the "green room" during the draft and was selected second overall by the Orlando Magic, later signing his rookie-scale contract with the Magic on July 8.

When the 2013 rookie class convened for its annual photo shoot and filled out its NBA.com Rookie Survey, the class voted Oladipo as the best defender, the co-favorite 2013–14 Rookie of the Year (with C. J. McCollum), the co-favorite to have the best career (with Kelly Olynyk) and second-most athletic (behind Tony Mitchell).

On December 3, 2013, Oladipo recorded his first career triple-double with 26 points, 10 rebounds and 10 assists in a double overtime loss to the Philadelphia 76ers. Rookie Michael Carter-Williams of the 76ers also recorded his first career triple-double in the same game, marking the first and only time in NBA history that two rookies have recorded triple-doubles in the same game. The last time that two players had recorded their first career triple-doubles in the same game was when Detroit Pistons' pair Donnie Butcher and Ray Scott did it on March 14, 1964 (they were not rookies). It was also the first time that two opponents had recorded triple-doubles in the same game since Caron Butler and Baron Davis had done so on November 23, 2007. During the month of February, Oladipo participated in the BBVA Rising Stars Challenge and the Taco Bell Skills Challenge. Oladipo went on to finish second in the Rookie of the Year voting behind Carter-Williams.

In Game One of the Pacers' first-round playoff series against the Cavaliers, Oladipo scored 32 points in a 98–80 win. He became the fourth player in Pacers history with at least 30 points and six 3-pointers in a postseason game, joining Reggie Miller, Chuck Person and Paul George. In Game 6, Oladipo recorded his first career postseason triple-double with 28 points, 13 rebounds and 10 assists in a 121–87 win, helping the Pacers force a Game 7. The Pacers went on to lose Game 7 to bow out of the playoffs despite Oladipo's 30 points, 12 rebounds, six assists and three steals.

In the 2012-13 season, despite an Indiana roster deep with talent, Oladipo emerged as one of the nation's biggest stars. Midway through the season, ESPN reporter Eamonn Brenann wrote, "In 2½ seasons in Bloomington, Oladipo has morphed from a raw athletic specimen to a defensive specialist/energy glue guy – he became a hit with IU fans for holding his hand in front of his face after dunks at home, typically after a steal he himself created – into a sudden, stunning, bona fide collegiate star." Due in part to Oladipo's leadership, the Indiana Hoosiers finished the 2012–13 season as the outright Big Ten champions. At the end of the regular season, Oladipo ranked fourth in the country in field goal percentage (61.4), on pace to have the highest field goal percentage by any guard since the 1996–97 season. Among Wooden Award finalists, he had the best net rating, which is the difference between points produced and points allowed per 100 possessions. Oladipo produced 42 more points than he allowed per 100 possessions.

In 2012–13, Oladipo played and started in all 36 games, averaging 13.6 points, 6.3 rebounds, 2.1 assists and 2.17 steals. At the conclusion of his junior year, Oladipo racked up numerous awards. He was named the Sporting News Men's College Basketball Player of the Year, the National Co-Defensive Player of the Year, and a first-team All-American by the USBWA and Sporting News. In conference honors, he was named a unanimous pick to the first-team All-Big Ten by both the coaches and media, and was named Big Ten Defensive Player of the year.

As a sophomore during the 2011–12 season, Oladipo averaged 10.9 points and 5.5 rebounds in 26.7 minutes per game (47.1% FG, 75% FT). Some commentators referred to him as Indiana's "most improved player this season", and he was often cited as the team's best defender. The team earned a #4 seed in the 2012 NCAA Tournament and defeated New Mexico State in the second round. After defeating VCU in the third round, the Hoosiers lost in the Sweet Sixteen to Kentucky, the eventual national champions.

During the 2010–11 season, Oladipo played in 32 games (five starts), averaging 7.4 points, 3.7 rebounds and 1.06 steals in 18.0 minutes per game, while shooting .547 from the field. He earned his first career start against Penn State on December 27 and responded with 14 points on 5-of-9 shooting, four rebounds, three steals, and two assists in 27 minutes of action.

Kehinde Babatunde Victor Adrian Oladipo (born May 4, 1992) is an American professional basketball player for the Indiana Pacers of the National Basketball Association. He played college basketball for the Indiana Hoosiers, where in the 2012-2013 season he was named the Sporting News Men's College Basketball Player of the Year, the Co-NABC Defensive Player of the Year, and a first-team All-American by the USBWA and Sporting News. That year he was also named the winner of the Adolph Rupp Trophy, given annually to the top player in men's NCAA Division I basketball. Oladipo was drafted with the second overall pick in the 2013 NBA draft by the Orlando Magic and went on to be named to the NBA All-Rookie first team. He was traded to the Oklahoma City Thunder in 2016, and then traded to the Pacers in 2017. He became a first-time NBA All-Star, led the league in steals, was named to the All-Defensive First Team and the All-NBA Third Team, and won the NBA Most Improved Player Award in his first season with Indiana. Despite an injury-riddled 2018–19 season, including a season-ending injury in January 2019, Oladipo was named an Eastern Conference All-Star reserve for the second straight year.