Payton appeared in a career-high 29 games for the Wizards in 2019-20. He set per-game career highs in points (3.9), rebounds (2.8), steals (1.1) and made threes (0.4). He shot 41.4 percent from the field, 28.3 percent from three and 50.0 percent from the free-throw line. Twice, he set a new career high with six steals in one game. First, he did it Dec. 23 against the Knicks. That contest was also his lone double-double (season-high 11 rebounds). He got six steals against the Knicks again on Dec. 28. In those two contests, he also combined for 25 points, 17 rebounds, seven assists and three triples. Payton's other single-game season highs were 15 points, five assists, two made threes and two blocks. Payton had five games with double-digit points, six games with at least five rebounds and eight games with at least three assists. He also grabbed at least one steal in 13 games and got at least one block in six games. In the nine contests that Payton saw at least 20 minutes, he averaged 6.9 points, 5.2 rebounds, 3.2 assists and 2.6 steals.

After a tryout with the Trail Blazers, Payton started the 2018-19 season with the G League's Rio Grande Valley Vipers. Payton appeared in 26 games with the Vipers over two stints with the squad. All told, he averaged 29.9 minutes of run over the G League season. The Oregon State product tallied 16.1 points, 7.2 rebounds, 6.6 assists, 3.0 steals and 0.9 blocks per G League contest. On Jan. 18, Payton scored a G League season high of 31 points to go with seven boards, three assists and two steals in a win over the Memphis Hustle. Three days later, Payton signed a 10-day contract with the Washington Wizards. He made his NBA season debut that evening, Jan. 21, during a brief appearance in a home win over the Pistons. Payton didn't play in the next three games, but on Jan. 29, he earned 12 minutes of run in a road loss at Cleveland. He posted 11 points, four assists, three steals and one block versus the Cavs. Payton then returned to the Vipers, and on the last game of the G League season, he generated 13 points, seven assists, three rebounds and a steal in a home win over the Sioux Falls Skyforce.

In mid-October, the Bucks released Payton, but then re-signed him two days later to a two-way deal. The 6-foot-3 guard played in 12 games (six starts) for Milwaukee and three games with the G League Wisconsin Herd before Milwaukee decided to waive him on Dec. 17. With the Bucks, Payton averaged 2.5 points, 1.4 rebounds and 0.8 assists over 8.8 minutes per game. With the Herd, Payton tallied 18.3 points, 7.0 rebounds and 2.7 steals per G League contest. Roughly a month after leaving the Bucks, Payton signed a two-way contract with the Lakers. He appeared in 11 games for Los Angeles and 17 contests for the G League South Bay Lakers. With South Bay, Payton generated 17.2 points, 6.2 rebounds, 5.1 assists and 1.9 steals per contest. With the NBA Lakers, Payton had his best outing in the last game of the season (April 11). Payton received over 30 minutes of run and produced 25 points, 12 rebounds, one assist and two steals in a win over the Clippers. It was his first career double-double. The Lakers finished with a 35-47 record and did not qualify for the postseason.

After going undrafted in the 2016 NBA Draft, Payton played for the Rockets in Summer League play. In late October, Payton joined Houston's D-League affiliate, the Rio Grande Valley Vipers. Over 49 games with the Vipers, Payton tallied 14.1 points, 3.3 assists, 2.0 steals and 1.5 three-pointers in 32.7 minutes. On Dec. 3, the rookie generated 51 points, 11 rebounds, three assists and one steal during a road win over the Los Angeles D-Fenders. On April 2, Payton signed a two-year agreement with the Bucks. He made his NBA debut that evening and delivered five points, one rebound and one three-pointer during nine minutes of floor time. Payton appeared in the Bucks' last six games of the season and averaged 3.3 points, 2.2 assists, 2.0 rebounds and 0.5 steals over 17 minutes. The Bucks finished with a 42-40 record and lost to the Raptors in the first round of the playoffs. Payton was not on the active playoff roster.