[9][10][11] In their third season under head coach Rick Pitino, the Celtics won their first three games, but played below .500 for the first few months, holding a 21–28 record at the All-Star break.
[12] At mid-season, the team traded Fortson to the Toronto Raptors in exchange for Alvin Williams, but the trade was voided due to Williams failing his physical exam; Fortson only played 55 games this season due to a stress fracture in his right foot.
[13][14][15][16] The Celtics struggled and suffered a ten-game losing streak between March and April, but managed to win five of their final six games, finishing fifth in the Atlantic Division with a 35–47 record, and missing the playoffs again for the fifth straight season.
[18] This season also reached a breaking point for the Celtics, after a 96–94 home loss to the Raptors on March 1, 2000, where All-Star guard Vince Carter hit a three-pointer at the buzzer, which even drew cheers from the Celtics fans at the Fleet Center; Pitino went on a legendary rant in his post-game interview, wherein he blamed fans and the media for being negative towards the Celtics, and demanded them to stop reliving past glories; best remembered by the phrase "walking through that door", as he referred to retired Celtics legends Larry Bird, Kevin McHale and Robert Parish, who all won three championships with the team in the 1980s.
[28][29][30] Meanwhile, Cheaney was traded to the Denver Nuggets,[31][32][33][34] and Pervis Ellison signed as a free agent with the Seattle SuperSonics.