The Pitino Files: Taking one of the biggest draft busts in Celtics history

Over the past few weeks here at BSJ, we have shined 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 five entries of the series here that chronicles Pitino’s first offseason, first big trade of Chris Mills, why the Chauncey Billups trade was even worse than you remember, why the Antoine Walker extension changed everything, betting the farm on Vitaly Potapenko, and a Ron Mercer trade that actually worked for Boston.

After a brief hiatus to save everyone from getting too depressed about the tenure, we are back to wrap up the series this week and how the era was bridged before Danny Ainge arrived. Next up: Pitino's last stand in the 2000 offseason. 

Setup
Offseason 2000

Draft Night

Coming off a 35-47 record in 1999-2000, the Celtics suffered their seventh straight losing season overall and third straight since Rick Pitino took control. He entered the summer of 2000 with all kinds of pressure to finally show some growth as a pair of All-Star caliber players entered their prime in Antoine Walker and Paul Pierce.

After years of wheeling and dealing, combined with handing out hefty long-term contracts and extension, Pitino did not have much trade or draft capital yet again as he approached the 2000 NBA Draft in June. The Celtics had already traded their second-round pick (No. 39 overall) two years earlier in a deal to get rid of new free agent signing Chris Mills so that left Boston with only one selection at No. 11 overall. The team’s payroll also remained far above the salary cap so as big names like Tim Duncan, Grant Hill and Tracy McGrady hit the open market, the Celtics only had the mid-level exception to spend ($2.5 million) on free agents beyond a veteran’s minimum exception.

That meant the lottery pick was going to be crucial as a clear path towards improvement for Pitino’s mismatched roster. The head coach had struck gold before at the end of the lottery (Pierce at No. 10 in 1998) and needed to hit again here to ensure this team started trending upwards.

Instead, Pitino settled on what ended up being the worst lottery pick in the draft at No. 11: 6-foot-11 Jerome Moiso. The UCLA sophomore was already 22 on draft night (red flag) and really never showed off an NBA skillset in his career despite his impressive length and athleticism. He averaged 1.5 PPG and 1.8 RPG in 24 games over his rookie season and was reportedly pushing for a trade as early as January 2001 as he failed to play his way into consistent minutes in the Celtics rotation.

Incredibly, the Celtics managed to get a first-round pick for him after his rookie season (from Philadelphia) but Moiso finished his career with just 2.1 win shares over five NBA seasons with four teams. Needless to say for Pitino, this wasn’t a guy that would be able to help right away as a rookie. That player (Andre Miller) was available last year at the C’s draft spot in 1999 (No. 8) but he ended up in Cleveland after Boston dealt away the selection for Vitaly Potapenko at the trade deadline.

To be fair to Pitino, there were all sorts of busts across the 2000 NBA Draft, one of the worst draft classes in NBA history. Only three All-Stars emerged out of the 58 draft picks (Kenyon Martin, Jamaal Magloire, Michael Redd) and none of those ever became elite guys. While there was some solid talent later in the teens in this draft (Hedo Turkoglu, Quentin Richardson, Magloire) the guys taken just after Moiso were mostly busts as well (Etan Thomas, Courtney Alexander, Mateen Cleaves, Jason Collier). Just a draft class full of misses.

To make matters worse, Pitino ended up making one more move on draft night, dealing away two future second-round picks for the right to Josip Sesar, who was taken at No. 47 overall by Seattle. If you haven’t heard of Sesar, that makes sense since he never ended up playing a minute for Boston or in the NBA in general.

Free Agency

The Celtics didn’t have much room on their roster for new players this offseason with so many guys locked in for the long-term already on deals that were tough to move. Pervis Ellison finally saw his mammoth contract expire but there were bloated contracts everywhere from Kenny Anderson to Vitaly Potapenko and Greg Minor that all had negative values attached to them.

With Dana Barros on his way out the door (more on that later), backup point guard ended up being a priority for Pitino on the free agent market. After swinging and missing on a shooting option (Tariq Abdul-Wahad signed with Denver instead), the Celtics spent their entire mid-level exception on Randy Brown.

Fans may remember Brown as a deep reserve on the Bulls during Michael Jordan’s three-peat. He wasn’t exactly playing a big role in those days (averaged just six minutes per game in 1996-1998 postseasons) but Brown had been given the starting guard role in Chicago under Tim Floyd after the champions broke up. The end results were not pretty. Brown couldn’t shoot and averaged just 6.4 ppg in 1999-2000 while hitting just 36 percent of his shots from the field. When you consider the fact he wasn’t even attempting 3s, that’s a horrific percentage and helps explains why the Bulls finished with a 17-65 record in 2000 with Brown playing big minutes.

Despite this, Pitino still handed over a three-year deal to the defensive-minded veteran for the full mid-level exception, hoping Brown would provide a defensive spark for Boston. All this for a guy who finished with -0.8 win shares in Chicago, the worst number on the entire team. As a painful footnote, Chauncey Billups ended up signing this offseason for the same amount ($2.5 million per year) in Minnesota in what was the beginning of his career turnaround.

Pitino’s other main free-agent addition? Another former Bull wing named Chris Carr, who was out of the league by the end of the 2000-01 season.

The Final Trades
August-October 2000

Armed with Brown and Carr, Pitino had a couple more trades to make to fortify the roster. The Celtics could not afford to keep underused big man Danny Fortson (which ended up being a good thing for Boston over the long haul), so the Celtics wisely found a way to sign-and-trade him. A four-team trade involving multiple sign-and-traded pieces was the end result with the C’s receiving a 2001 Jazz first-round pick, cash, point guard Robert Pack and an injured John Hot Rod Williams in exchange for Fortson and Dana Barros.

Pitino immediately lined up another deal that couldn’t be executed until midway through training camp (not exactly ideal) that shipped off Pack and last year’s failed big free agent signing (Calbert Cheaney) to the Nuggets for shooting guard Bryant Stith and hometown point guard Chris Herren.

Stith ended up being a solid contributor for the C’s in 2000-01, ranking third on the team in ppg (9.7). The problem is he was well past his prime at age 30 and was miscast as a third-best scoring option on the team at this point in his career. The Celtics really didn’t have anyone that could play that role on this roster, especially after a declining Kenny Anderson got hurt early in the year (played just 32 games all year).

Without Anderson running the show (hurt in second week of season) the Celtics were forced to rely on the likes of Brown, Herren and Milt Palacio to run the offense. Journeymen like Doug Overton and Rick Brunson were also brought in for cups of coffee at point guard and none of those stints went well. The big investments made in guys like Vitaly Potapenko, Eric Williams, Walter McCarty and Tony Battie weren’t paying off as they were all limited offensive role players.

Beyond Pierce and Walker, there was limited shooting and shot creation ability across the entire roster and players were growing tired of Pitino’s defensive system of pressing.

After starting the season 7-7, the C’s dropped 10 of their next 15 games, including six straight heading into January, which dropped the team to 12-22, which ended up being the final straw for Pitino.

Next Up: Pitino says goodbye and the Celtics immediately start turning things around.