[5] On October 9, he suffered a grade III sprain of the medial collateral ligament (MCL) in his right knee.

[10] On September 23, 2016, O'Bryant signed with the Washington Wizards,[11] but was later waived on October 21 after appearing in four preseason games.

[12] On November 11, 2016, O'Bryant was acquired by the Northern Arizona Suns of the NBA Development League.

[13] He made his debut for the Suns in the team's season opener the following day, recording 18 points and 12 rebounds in a 122–106 win over the Iowa Energy.

[22] On February 7, 2018, O'Bryant, along with two future second-round draft picks (2020 and 2021), was traded to the New York Knicks in exchange for Willy Hernangómez.

[24] On July 31, 2018, O'Bryant signed a one-year deal with the Israeli team Maccabi Tel Aviv of the EuroLeague.

[25] On December 27, 2018, O'Bryant recorded a career-high 32 points, shooting 5-of-7 from 3-point range, along with five rebounds, three assists and three steals for 44 PIR, leading Maccabi to a 94–92 win over Olimpia Milano.

[31] On January 27, 2021, he received a 10-day suspension from the club due to a conflict with team head coach Dejan Radonjić during a game against Anadolu Efes.

[34] On February 21, 2021, O'Bryant signed with Türk Telekom of the Turkish Basketball Super League, for the remainder of the season.

[37] On November 15, 2021, O'Bryant signed with the Wonju DB Promy of the Korean Basketball League to replace Yante Maten for eight weeks.

[48] On July 12, 2024, O'Bryant signed with the Gigantes de Carolina of the Baloncesto Superior Nacional (BSN).

[51] On January 13, 2025, O'Bryant signed with the Anyang Jung Kwan Jang Red Boosters of the Korean Basketball League (KBL) to replace Cliff Alexander.