Pitino Files: Why the Chauncey Billups trade was even worse than you remember

Over the upcoming weeks here at BSJ, we will be shining a microscope on one of the most tumultuous eras in Celtics history: Rick Pitino's tenure as coach and team president. You can check out the first two entries of the series here that chronicles Pitino's first offseason and first big trade of Chris Mills. Next up: Pitino goes shopping at the trade deadline with disastrous results.

The Setup

February 18, 1998 — Trade deadline. Celtics are 23-28 in Year 1 of the Pitino era. 

The opening season of the Rick Pitino era was far from perfect but it was actually a pretty encouraging start for such a young roster amid an offseason full of foolish signings. After having two key veterans dealt away (Mills, Massenburg) during training camp for unproven talent, the Celtics were a respectable 23-28 heading into the trade deadline. Antoine Walker was the team’s top scorer (22.4 ppg) as expected with rookie shooting guard Ron Mercer (15.3 ppg) serving as a decent second option. Behind them? The only other player on the roster was averaging double-digit points was 21-year-old rookie point guard Chauncey Billups (11.1 ppg).

Billups wasn’t exactly doing it efficiently (39% FG) but there were plenty of signs of promise throughout his 25 minutes per game. He was second on the team in free throw attempts per game (3.5) and led the team in assists (4.3) despite being a shoot-first point guard. He scored 20-plus points in five games, cementing himself as a starter in November.

“I had finally started to play well,” Billups told Grantland in 2012 about his rookie year. “The fans had started to embrace me and took me in. The team was all right, up and down. But I was finally starting to make my way and boom, the last day of the trading deadline, I get traded.”

We all know how big of a mistake the Billups trade was in hindsight after seeing the C’s give up on an eventual five-time All-Star in year one of his career. However, a closer inspection of the move reveals the sheer madness of selling low on the No. 3 overall pick in real-time for Boston for an overpaid veteran point guard. To understand the lasting impact of the deal from a team-building perspective, we have to look more at the prized name coming to town in Kenny Anderson and why he was so available in the first place.