The Pitino Files: Exploring the perplexing Chris Mills trade in 1997

(Andy Lyons/Getty Images)

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 entry of the series here that chronicles Pitino's first offseason. Next up: An eventful preseason for the head coach before his regular season. 

Rick Pitino’s first NBA offseason in Boston primarily centered on bringing aboard youth with a couple of notable exceptions. The head coach dumped four of the team’s top five scorers from the previous season in order to open up major salary cap room to bring aboard a mix of young unproven players on sizable deals (Knight, DeClercq, Edney).

Two players that did not fit that mold for a rebuilding Celtics squad were former Cavs swingman Chris Mills and big man Tony Massenberg. Mills ended up being the top player Pitino brought aboard in his first summer at the helm in Boston, inking him to a seven-year, $34 million deal in August to be the No. 2 scorer on the team next to an emerging Antoine Walker.

The 27-year-old Mills was an scorer with 3-point range (12.6 PPG in Cleveland over his first four seasons) but was far from an All-Star. He was an offense-first player, which made him a questionable fit for Pitino’s pressing system that emphasized ball pressure and speed on the defensive end. The Celtics paid a hefty price for Mills not only with his hefty contract but also dealing away promising small forward Eric Williams for two second-round picks in order to open up the necessary salary cap room to sign the older Mills inflated deal.

The other veteran signing for the C’s was 29-year-old big man Massenburg, who was coming off a career year for John Calipari in New Jersey. Massenberg had played for eight teams in his first eight seasons but had turned into a proven rebounder by the mid-90s that could help a team off the bench. That was enough for Pitino to hand him a three-year, $2.7 million deal in his offseason shopping spree.

In today’s day and age, teams can no longer even deal newly signed free agents before a season begins. Instead, they must wait until December 15th before making such a move. This restriction was added into the NBA collective bargaining agreement in the 2000s, but it’s safe to believe Pitino’s decision in the preseason of 1997 helped lead to that shift after he elected to deal away two of his offseason signings before the year began

October 23, 1997

Celtics trade to Knicks: Chris Mills, 1998 second-round pick, 1999 second-round pick

Celtics receive from Knicks: Walter McCarty, Dontae Jones, John Thomas, Scott Brooks

The 'rationale' behind trade: Mills was far more of a scorer than a defender and that did not make his transition to Boston seamless during that postseason. He also reportedly took issue with the hard two-a-day workouts and constant pressing that Pitino demanded of his players even during the preseason. After reportedly speaking with Pitino about his concerns before the regular season began, Pitino opted to remove the potential point of dissension in his locker room in order to land additional younger players.

While Pitino’s rationale of going younger made sense, there were a couple of problems with his decision:

1. Dealing Mills after dumping young proven players to sign him in the first place: The Celtics let go of Eric Williams, David Wesley, and Rick Fox among others during Pitino's first summer to bring aboard the high priced Mills on an absurdly long deal. Trading him with seven years attached at a high price tag attached was going to be a challenge but a strong season as a top scorer in Boston could have helped his stock. Instead, the Celtics had to attach two future second-round picks with Mills in order to justify the Knicks taking on the deal and including some fringe first-round talent. Remember, the C’s got those second-round picks for dealing away 15 ppg scorer Eric Williams (earning $1.5 million) in order to sign Mills in the first place, leaving the C’s with a net result of zero from that transaction beyond the 'talent' they got for Mills. And about that talent...

2. Pitino’s eye for young talent was dismal.

A quick rundown of what Pitino received in this deal:

Walter McCarty: The second-year forward turned into a solid bench player for the Celtics during his 10-year NBA career. However, when the C’s acquired him, the No. 19 pick in the 1996 NBA Draft has been buried on a deep Knicks roster, averaging just 1.8 ppg in his rookie season over 35 games. "We've had our eye on Walter McCarty for some time," Pitino said at the time of the trade.

Dontae' Jones: The 22-year-old Jones had missed his entire rookie season with a broken left foot after serving as a standout for Mississippi State in the mid 90s against Pitino’s Wildcat teams. He had always missed the entire preseason for the Knicks in year two before the trade, giving him essentially no trade value to the league after being taken No. 21 overall in the 1996 NBA Draft next to McCarty.

"Jones is the X factor," Pitino said in October 1997. "He could be a great player for us. Or he could be a bust. I know he single-handedly busted our tails when he was at Mississippi State."

Well, at least Pitino nailed this prediction. Jones proceeded to play 15 games and 91 minutes in his Celtic career before being waived in 1999. He spent the rest of his career overseas.

John Thomas: The rookie big man had been taken No. 25 overall by the Knicks in the 1997 NBA Draft, adding to the parade of limited upside forwards that Pitino coveted in the bottom half of NBA Draft. Thomas played just 33 games for the Celtics, averaging 2.8 ppg in 1997-98 before being dealt away to Toronto as part of the trade package for Kenny Anderson. Thomas played until 2006 but spent most of his career overseas, averaging just 2.7 ppg in the NBA over 208 games.

Scott Brooks: The current Wizards head coach was at the tail end of his NBA career in this trade and was just included for salary cap matching purposes. He was waived before the season even began.

Getting rid of what ended up being an albatross contract for Mills ended up being one of the few of Pitino’s own mistakes that he was able to rectify in Boston. The swingman did not fit the timeline of a rebuilding squad and was overpaid well into his 30s thanks to Pitino’s initial contract when injuries derailed his career. However, the lack of foresight by Pitino in this scenario is maddening in hindsight for Pitino given his vision (or lack thereof) for what he wanted this team to be. Dumping talented players over the summer to sign Mills and then moving Mills months later for unproven cheap players helped to streamline a startling lack of talent on the roster in the Pitino era and led to more mistakes.

Incredibly, Pitino wasn’t even done dealing before his first season began: