Pinkston was selected to play in the McDonald's All-American Game during a stellar career at Bishop Loughlin Memorial High School.
Pinkston recalls being awful at first, but began to show signs of improvement after training with his cousin Tyren for several years.
[4] Pinkston attended Bishop Loughlin Memorial High School, where he played basketball under three different head coaches.
[5] He was suspended academically midway through his junior season and considered transferring to a different school, but instead improved his grades.
[2] In his first game back from suspension on March 5, Bishop Loughlin edged St. Raymond's 77-74 behind 31 points from Pinkston.
[6] As a senior, Pinkston averaged 25 points, 13 rebounds, five assists and two blocks to lead Bishop Loughlin to the CHSAA Class AA intersectional final.
"[8] He was selected to the Parade All-American second team and was named New York's Player of the Year as a senior.
[9] The Daily News reported that multiple sources expected JayVaughn to sign a letter to attend the University of Tennessee over Villanova and St. John's, but sources with knowledge of Pinkston's thinking say he reconsidered his decision, discussed it with his family and decided to hold off until the late signing date.
The Upper Merion Township police arrested and charged Pinkston with two counts of assault and harassment.
[10] Pinkston was named Big East Rookie of the Week on January 23, 2012, after posting 13 points and 12 rebounds against St.
[3] Teammate Ryan Arcidiacono thought the major health scare changed Pinkston's outlook on life, making him a more humble person.
[14] He was selected to the District II (NY, NJ, DE, DC, PA, WV) All-District team by the United States Basketball Writers Association (USBWA).
[15] Pinkston was listed on the National Association of Basketball Coaches Division I All‐District 5 second team on March 12.
[16] The New York Post named Pinkston the preseason Big East Player of the Year as a senior.
[18] In its preseason rankings of the best players in college basketball, ESPN listed Pinkston at number 39.
[24] On March 25, 2016, he was acquired by the Maine Red Claws of the NBA Development League,[25] but didn't play for them.
[26] On July 30, 2016, Pinkston signed a one-year deal with the Italian team Dinamica Mantova of the Serie A2.
[28] On March 18, 2018, Pinkston recorded a career-high 37 points, shooting 12-of-23 from the field, along with ten rebounds and four assists in a 106–117 overtime loss to AZS Koszalin.
[29] In 30 games played for Krosno, Pinkston averaged 18 points, 5.8 rebounds, 1.8 assists and 1.4 steals, shooting 42.4 percent from 3-point range.
On August 2, 2018, Pinkston signed a two-year deal with the Israeli team Hapoel Holon.