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"