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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.

[caption id="attachment_566118" align="alignnone" width="1024"] 25 Jun 1997: Guard Chauncey Billups of the Boston Celtics shakes hands with NBA Commissioner David Stern during the NBA Draft at the Charlotte Coliseum in Charlotte, North Carolina. Mandatory Credit: Craig Jones /Allsport[/caption]

Anderson’s holdout leads to Pitino’s overpay

While today’s NBA has become notorious for stars wielding power over their franchises via trade demands and threatening not to re-sign, this really isn’t a new development in the NBA. In most scenarios throughout history, a veteran demanding a trade or failing to report puts their current team in a tough spot when it comes to receiving fair compensation. Look no further than Kawhi Leonard’s departure from San Antonio for an example of how a public demand and refusal to play can come back to bite a team.

Before the Celtics acquired Kenny Anderson 22 years ago, the Toronto Raptors found themselves dealing with plenty of trade demands and holdouts ahead of a busy trade deadline. A miserable 1-15 start to the season soured franchise point guard Damon Stoudemire on playing for the franchise and he asked out ahead of hitting free agency. Toronto found some decent value for him ahead of the trade deadline by sending him to Portland (who outbid the Knicks) with a couple of role players (Carlos Rogers, Walt Williams) in exchange for Anderson, two role players (Gary Trent, Alvin Williams) and two 1998 mid-first round picks on February 13th, five days ahead of the trade deadline. That’s a solid haul for Toronto given the circumstances, except they had one problem when the deal got done: Anderson was refusing to report to Toronto.

Anderson had been an All-Star for the Nets in 1994 but this trade to Toronto was the second time he had been traded since 1996. The Nets shipped him to Charlotte in 1996 when he asked for more money than they wanted to give him before hitting free agency. The Hornets got Anderson as a rental and only kept him for a half-season, refusing to pay his asking price in free agency as well. Ultimately, the Blazers stepped up to the plate with a massive seven-year, $50 million deal that landed the New York native.

Anderson was getting paid like an All-Star but he was anything but that already in the second year of his seven-year pact with Portland in 97-98. He was averaging just 12.6 ppg (lowest since his rookie year) and shooting a career-low 38.7 percent from the field. In fact, his numbers were pretty comparable to Billups with a far heftier price tag attached. Combine that with the fact that Anderson was bumping heads with head coach Mike Dunleavy and that left Portland looking to shake up a playoff squad that wasn't going anywhere.

With five years left on his contract, the Blazers were clearly looking for an exit hatch in 1998 from Anderson, seeking to invest in the younger Stoudemire instead as their big-money point guard of the future. Ultimately, they gave up Anderson and a couple picks to get the deal done, with Blazers owner Paul Allen agreeing to pay the remainder of his contract (five years, $38 million) to help get him out the door and save Toronto cash while landing Stoudemire. The problem? Anderson showed no real interest in playing for a cellar dweller in Toronto for the next half-decade. He failed to report after the trade, which should have put Toronto in a tough spot when it came to negotiating a return for Anderson in a subsequent deal.

Luckily for them, Pitino was on the other end of the phone line when they started shopping Anderson around. Normally, a team might have been soured on a player that had played for four teams in the last three years, was in the midst of a career-worst season, had bumped heads with his head coach and was dealt away with his entire contract paid for in order to get a blockbuster deal done. Even if Pitino liked Anderson as a buy-low addition, the key term there for any deal had to be the buy-low part. He had the leverage with Toronto with Anderson failing to report to play, which would undoubtedly cause his trade value to dwindle if they held onto him pass the trade deadline. There was also the matter of the five years left on a sizable contract attached to the player that had been underperforming.

“While it wasn’t a foregone conclusion that Kenny Anderson would be traded, and we were expecting to keep him even if that meant suspending him for reporting late to Toronto,” Raptors general manager Glen Grunwald told SI at the time. “The trade with Portland was structured in such a way that option could be contemplated. We explored different possibilities before Boston stepped forward with an excellent offer that enabled us to add four quality players.”

So what exactly would the fair market value be in this instance for Anderson? Let’s look no further to the Stoudemire deal for a comparison. The Raptors got two mid-first round picks plus Anderson’s bad deal (with cash attached for it) and a couple meh role players (Trent, Williams) for an emerging star in Stoudemire. There is no way the Raptors should have received more for an overpaid Anderson than Stoudemire. Yet, that’s the situation the Raptors found themselves in when meeting Pitino at the negotiating table.

The Trade

Celtics get: Kenny Anderson, Zan Tabak, Popeye Jones
Raptors get: Chauncey Billups, Dee Brown, Roy Rogers, John Thomas

This deal was not a one-for-one, so it’s important to look at it from a big picture perspective. The Celtics were giving up a No. 3 overall pick so there must have been more to the story looking back. Did they get to dump bad money? Pick up a good prospect or two with long-term control besides a bloated Anderson contract? A closer inspection of the deal reveals none of these things occurred.

[caption id="attachment_566120" align="alignnone" width="1024"] Mandatory Credit: Ezra O. Shaw /Allsport[/caption]

Point guard comparison

A quick look at the deals involved for the point guards"

Anderson’s contract at time of deal

97-98: $5 million (age 27)
98-99: $5.8 million
99-00: $6.6 million
00-01: $7.5 million
01-02: $8.3 million
02-03: $9.1 million

Overview: A reminder here that the salary cap in 97-98 was just $26 million, meaning Anderson was paid roughly 15-20 percent of the salary cap for the entire length of his contract. He never averaged more than 14.0 ppg with the C’s, serving as an overpaid third option during his entire career. Pitino did manage to get the Raptors to pay for Anderson’s salary for two seasons (97-98, and 98-99) but his number still counted against the salary cap. Also, how much of a concession was that really considering the Blazers had agreed to pay the Raptors for Anderson’s entire contract when they made their deal? Boston got some short-term savings for its payroll but was still on the hook for the worst part of Anderson’s deal as he entered his 30s,  a reality that led to it eating up critical cap room and flexibility as Paul Pierce and Antoine Walker entered their primes in the early 2000s.

Billups contract at the time of deal

97-98: $2.3 million
98-99: $2.7 million
99-00: $3.1 million

Overview: Billups was on a three-year rookie deal that paid him less than half of what Anderson earned over the next three seasons before he hit free agency in 2000. Even though Billups didn’t turn into an All-Star until 2005, his numbers in Toronto, Denver and Minnesota still exceeded what Anderson’s were by 2000 once he found a better team (Minnesota) and got over his injury woes. Billups made a combined $13 million over his first five NBA seasons, something that would have made him a pivotal low-cost piece for the Celtics if he was allowed to grow alongside Pierce and Walker in Boston during that era. That trio (with some more help) could have given the Nets a stronger run for their money in 2002 and 2003 with the added help that could have been sought out in free agency instead of a declining Anderson in that span.

[caption id="attachment_566117" align="alignnone" width="1024"] 29 Dec 1997: Guard Chauncey Billups of the Boston Celtics looks on during a game against the Los Angeles Lakers at the Great Western Forum in Inglewood, California. The Lakers won the game, 106-102. Mandatory Credit: Jed Jacobsohn /Allsport[/caption]

So why the infatuation with Anderson from Pitino’s perspective? He was a traditional point guard, unlike the score-first guard in Billups.

"Kenny can run the pick and roll very well," Pitino told reporters after the trade deadline. "When the offense is not there, he'll be able to create a little bit, get in the lane a little bit more. Kenny reminds me a lot of a point guard that was great for the Celtics -- Tiny Archibald. If he can be that good, we've got ourselves quite a gem."

Meanwhile, the Raptors made out well leveraging Billups into even more assets after making the deal. He finished the season with Toronto but was dealt before the start of the 99 lockout season to Denver in a three-team deal that landed Toronto two first-round picks including one that ended up being No. 5 overall from Denver in the 1999 NBA Draft. This was a sign that Billups still had good value around the league at this point. Keeping youth or acquiring more picks for youth was generally the smart way for rebuilding franchises to go like Toronto. That didn’t apply to the Pitino Celtics.

What about the other parts of the trade?

It actually just looks worse here for Boston when other names get involved. Let’s break down each piece:


Dee Brown: Brown was the third-best player in the deal, making $3.5 million in 97-98, with two years left on his deal for 7.7 million. He was a bit overpaid but still a useful veteran heading into his 30s, along with a good locker room presence. He averaged 11.4 ppg for the Raptors in 98-99, helping them climb up close to the .500 mark. In this trade, he was added to make the money work. If the C’s held onto him, they could have sold him off for a young player or pick in the next year or two instead of adding to the overpay.

John Thomas: The rookie big man acquired in the Chris Mills deal just months earlier was given up on by Pitino just months later (sense a trend?). Thomas was an inconsequential loss in this instance as he remained a third-string center for a five-year NBA career, making the Mills trade look even worse. He averaged 2.8 ppg in 115 games for Toronto before heading overseas in 2000.

Roy Rogers: Another young big man was acquired by Pitino for Tony Massenburg before the C’s season started. He only played nine games for Boston before being included as throw-in during this deal. He only played six games for Toronto

Okay, so the C’s gave up a No. 3 overall pick rookie showing promise, a decent veteran and a couple fringe NBA guys for Anderson. What else did they get in return?


Popeye Jones: The 27-year-old power forward was the other ‘key’ piece to this deal for Boston. The rebounding big man led the Raptors in boards during the 96-97 season, not exactly that impressive when you look at the talent on that roster, but hey it’s something right! He also averaged a double-double for the Mavs in two seasons before getting dealt to the Raptors. His numbers (8.6 ppg, 7.3 rpg) weren’t bad at the time of the deal. The problem? Jones had torn his left ACL in December for the Raptors which had ended his season. He also was in the final year of his contract at the time, meaning the C’s would have to pay big money in order to retain a guy coming off an ACL tear the following season. Spoiler alert: The Celtics did this, giving him a three-year, $8 million contract in January 1999 after the lockout ended. He played 18 games on the first season of that deal due to left knee issues (who could have guessed?). Pitino traded him away that offseason.

Zan Tabak: Like Jones, Tabak was a big man on an expiring contract when the C’s acquired him. He managed to play 18 games for the C’s at the end of the 97-98 season but did not re-sign. He headed to Turkey during the lockout and only played two more underwhelming seasons in the NBA.

In total, the Celtics got 32 games total and one bad contract (Jones) out of the other pieces to this deal.

The Aftermath

Anderson was given the keys to the car in Boston upon his arrival in Boston in February 1998.

“Coach Pitino has told me to take the ball and just run the team,” Anderson said. “That’s what I love. That’s what I did my first year in Portland. People started second-guessing Kenny Anderson. This system will help me get back to the way Kenny Anderson was. I’m not saying I’m a savior, but with the respect teams show for me, I’m going to make everyone’s job a lot easier.”

Anderson’s career in Boston was steady but largely unspectacular. He had a standout year in 2000 and helped guide the C’s on a deep playoff run in 2002 but his sizable contract served as a massive roadblock to add talent during his five years in Boston (more on that to come).

For 1998, the upgrade at point guard over the youthful Billups didn’t mean much. The Celtics finished the year with a 13-18 record after the trade, going 36-46 for the season. Anderson averaged just 11.2 ppg and 6.3 apg before shutting it down early for the season to rest up for 1998-99. Outside of Antoine Walker and Ron Mercer, Boston’s offseason overhaul produced no real appealing assets beyond a solid role player in Walter McCarty and a feisty defensive guard in Bruce Bowen. Travis Knight, Andrew DeClercq and Tyus Edney all underwhelmed, sending Boston into the draft and free agency with the No. 10 overall pick and few other ways to add to the roster.

Next up: A lockout season in 98-99 produces an underrated Pitino mistake.