Inside Rick Pitino’s disastrous first offseason with the Celtics

(Andy Lyons/Getty Images)

It’s been nearly 25 years since Rick Pitino took control of the Boston Celtics, kicking off an era of dramatic disappointment that set back the franchise through the tail end of the 1990s and beyond. Most Boston fans would probably like to block out most of this era (beyond the drafting of Paul Pierce) but given the dearth of sports news during this quarantine, I decided this would be a good time for a fuller look at Pitino’s body of work.

Growing up as a teenager in Pitino’s reign, there was always the understanding from afar that he wasn’t making the right moves and his players weren’t responding to the hard practices and relentless full-court pressure strategy over his four years at the helm. However, after going down a research rabbit hole with his specific moves and their sequencing, it feels like some of these decisions need to be put in perspective over two decades later, along with the underlying impact on the franchise. With that in mind, let’s dive headfirst into getting a closer look at some of the biggest missteps of the Pitino era, which practically started from day one.

Year 1 of the Rick Pitino Era
Summer 1997
Overview: The former Kentucky head coach took control of the Celtics just ahead of the NBA Draft Lottery in 1996. While the narrative was always about missing out on Tim Duncan for Pitino, the fact was despite having two picks in the lottery, the C’s only had a 36 percent chance at landing the No. 1 pick. They held steady with the Mavericks pick at No. 6 (sixth-worst record) and dropped from the best odds at No. 1 to the No. 3 pick in the draft when the Spurs (Tim Duncan) and Sixers (Keith Van Horn) leapfrogged them.

That left the Celtics with two top-six picks in what ended up being one of the weakest draft classes in NBA history after Duncan went at No. 1 with just three All-Stars among the 57 picks. Pitino seemingly drafted his backcourt of the future with Chauncey Billups at No. 3 and Ron Mercer at No. 6, leading into a pivotal summer for Pitino, who was looking to revamp a 15-win roster.

A Disasterous Free Agency

NBA salary cap rules have evolved plenty over the years but the main principals were still in place in the summer of 1997 when Pitino took control along with general manager Chris Wallace. The Celtics had the ability to create significant salary cap room but in order to do so, they would need to renounce the ‘Bird Rights’ on several of their own free agents. Normally, teams do not overhaul their own roster and renounce players in order to up significant cap room unless it's for a significant upgrade. The Celtics didn’t do it for nearly 15 years during Danny Ainge’s tenure as president until the summer of 2016 when Al Horford was signed for a max contract.

All-Star names weren’t available on the free-agent market in the summer of 1997. In fact, it was a very quiet summer when it came to big names. Power forward Brian Grant (Blazer) signed the biggest deal of the summer as a parade of solid starters/role players (Bobby Phills to Charlotte, Clifford Robinson to Phoenix, and Bison Dele to Detroit) switched squads with the big fish staying put.

For a 15-win squad, normally this would be the type of offseason when you want to punt on dumping your own talent to clear cap room. None of those names listed above are worth reconfiguring your entire roster or future plans. Yet, as Pitino sought to make a splash immediately, he decided he wanted to clear the deck of arguably the best young talent on Boston’s roster.

Eight Celtic players were released or renounced in the first month of free agency by Pitino.

Some of these names were guys that he shouldn’t have had an interest in keeping around (Brett Szabo, Steve Hamer, Nate Driggers, Marty Conlon) but there were a few key pieces also cast to the side as well.

David Wesley (16.8 ppg/7.3 apg) was a 26-year-old that was allowed to walk and sign with the Hornets on July 1st for reasonable money ($2 million/year). The same went for 27-year-old Rick Fox (15.4 ppg), who eventually signed a cheap deal with the Lakers in August after weighing plenty of suitors who offered up to $5 million per year.

Electing to let Wesley and Fox go without compensation opened the door for Pitino to make his first big