During the 2018-19 season, JaKarr Sampson appeared in four games for the Chicago Bulls. He also played in 24 games for the G League's Windy City Bulls. Chicago was Sampson's fourth NBA team since leaving St. John's in 2014. Sampson played all four of his NBA games in April, and made the most of his opportunity. The 6-foot-7 wing averaged 20.0 points, 8.0 rebounds and 1.8 steals-plus-blocks over 32 minutes per NBA contest. That included a 29-point career high during a loss to the 76ers on Apr. 6. Before playing for Chicago, Sampson delivered an impressive 21.1 points, 9.1 boards and 1.8 steals-plus-blocks per game for Windy City. Sampson also shot an accurate 54 percent from the field for the G League Bulls. He also shot 30 percent from three point land for Windy City. Sampson will enter the off-season as a free agent.

Fresh off a 2016-17 campaign in which he spent the entirety of the season in the G-League, Sampson signed a two-way contract with Sacramento in July. He saw action in 22 games with the Western Conference franchise and started six times during that span. Sampson started a pair of games in December, one on Valentine's Day, and then each of Sacramento's final three regular season contests. The former St. John's star was productive offensively - 4.7 points, 3.5 rebounds - despite averaging just 15.6 minutes per contest. His best offensive performance of the season was a massive six-point, 16-rebound effort against Cleveland on December 6. Sampson was highly efficient from the field as well, shooting 54.3 percent. A former Big East Defensive Player of the Year, Sampson also averaged 1.0 block per game. He posted a season-high four rejections in a one-point with over the Lakers on April 1.

Sampson spent the 2016-17 season in the D-League with the Iowa Wolves. He played 47 games (22 starts), seeing an average of 25.9 minutes. During that time, he averaged 15.1 points, 5.8 rebounds and 1.3 assists. Sampson shot 48.8 percent from the field, 28.4 percent from downtown and 68.8 percent from the free-throw line. Sampson set single-game season highs of 36 points, 12 rebounds, four assists, three steals (five times) and three blocks (three times). His best overall performance took place during a loss to the South Bay Lakers. Sampson played 23 minutes off the bench and posted 27 points, five rebounds, three assists and two blocks.

Sampson began the 2015-16 season with the 76ers. He appeared in 47 games (18 starts) with the team and averaged 5.1 points and 2.7 rebounds in 14.7 minutes. However, he was waived Feb. 18. He was picked up by the Nuggets on Feb. 22 and proceeded to appear in 26 games (22 starts) with Denver. He saw 18.0 minutes per contest, averaging 5.2 points and 2.3 rebounds. On the season, Sampson set new career highs in rebounds per game (2.6) and field-goal percentage (44.2). He also set a new single-game high with four blocks. His best performance of the season occurred as a member of the Nuggets on April 8 during a four-point win over the Spurs. Sampson started and played 25 minutes, recording 16 points (6-8 FG, 1-2 3Pt, 3-4 FT), four rebounds, two steals and one block. The Nuggets finished the season 33-49 and did not make the postseason.

Following two seasons at St. John's, Sampson went unselected during the 2014 NBA Draft. However, he impressed the 76ers enough to earn a contract. Sampson made his NBA debut during the opening night of the season, Oct. 29 against the Pacers. He played eight minutes off the bench and posted one rebound. Overall, he appeared in 74 games (32 starts) for the team. In 15.3 minutes per game, he averaged 5.2 points, 2.2 rebounds and 1.0 assists. Sampson set single-game career highs of 22 points, eight rebounds, six assists, three steals and three blocks. His best performance of the season was Apr. 15 during a four-point loss to the Hawks. He posted 22 points (8-15 FG, 0-5 3Pt, 6-7 FT), six assists, five rebounds, three steals and one block in 36 minutes.