Sixteen years ago, the NBA's most storied franchise reached into the college ranks and snatched up the charismatic coach from Kentucky, plying him with draft lottery hopes and promises of unprecedented power over the organization's decisions.
It was a catastrophic failure.
Pitino went just 102-146 in three-and-a-half seasons as the Celtics head coach, general manager and president.
Obsessed with winning on his terms and driven to impose his will on the team, Pitino brazenly alienated his players and the city of Boston. Just as disastrously, the slickest press-conference charmer in the business uncharacteristically lost his cool in front of the media as the on-court defeats mounted.
After such a calamity, you'd have thought that the Celtics would be reluctant to hire another successful coach from the amateur ranks. Boston's unmitigated disaster certainly served as a warning to the rest of the league, as no NBA team had signed a prominent college coach since Pitino's midseason resignation in 2001.
Until Boston hired Butler's Brad Stevens on July 3, 2013.
The Celtics are heading into a new era, and it'll be critical for them to examine the lessons of the much darker time in their not-so-distant past. The Pitino experiment didn't work out but, by looking at what went wrong in that sad chapter of Boston's history, perhaps it'll be easier to avoid a similar ending this time around.
Lesson 1: It's Not About You
"Pitino is very much a 'me' person," says Brown, who is now with the Orlando Magic. "People come to games to watch me coach—that's how he thinks."
-Dee Brown, as quoted by Ian Thomsen of Sports Illustrated in 1997.
Maybe it's unfair to parse words retroactively, but look back at the transcript of virtually any interview with Pitino during his time with the Celtics and you'll notice how frequently he used the first person. It's as though he could only discuss a subject as it pertained directly to him.
Given the chance, he effortlessly converted common questions into opportunities for self-aggrandizement. When Michael Holley of the Boston Globe asked him to comment on Antoine Walker's decision to shrug off voluntary workouts in 1998, Pitino responded:
Look, this is the way I am. All of my players are like children to me, especially the Kentucky kids. I am loyal to all of them. If my kids don't come home on time, do I stop being their father? Of course not. I don't turn on my players.
My job is to be extremely loyal to them. If I don't like something Antoine said, he is still my college basketball player and I love him dearly. He's going to get a lot of love from me and he's going to get a lot of discipline from me, too. I say this about all my players: They'll appreciate me more when their careers are over.
I wouldn't be so sure about that, coach.
To be fair to Pitino, his confidence was earned. He'd been a victory machine at Kentucky, and even enjoyed some success in his two seasons with the New York Knicks from 1987-89.
Plus, the Celtics treated him like a king. The 10-year, $49 million contract was one thing, but the team also stripped Red Auerbach, a living, breathing God in Celtics lore at the time, of the team presidency to give it to Pitino.
How could he not assume that the world revolved around him?
The hot-shot act always played well with college kids, most of whom were eager for leadership and willing to listen to Pitino's directives. But NBA players were a different story. Pitino's ego and desire to make himself the center of attention only served to irritate veterans and stifle the growth of younger players.
According to Jen Slothower of NESN.com, Stevens' personality won't result in the same mistakes:
His way of leading is providing a place for players to be their best, not making himself—or any pressures of the moment—the center of attention. Many a college coach has been unable to set his legend aside to lift a team instead. Stevens hasn't let such a legend form.
Lesson 2: Don't Micromanage
"I saw Pitino adhere stubbornly to his system: shuttling guys like chess pieces, micromanaging every second of every game, sticking with presses the team couldn't possibly sustain over a full season—in short, slowly sucking the life from his players."
-Grantland's Bill Simmons in ESPN The Magazine, March 3, 2003.
Admittedly, this second lesson is an extension of the first one. Pitino's coaching style, just like the persona he employed in interviews, was very much "Rick-centric." On the court, that meant he had to win on his own terms.
The full-court presses and mass substitutions that led to so much success in college were going to define his Celtics teams, consequences be damned. Even when it became clear that the desired results of Pitino's preferred style—forced turnovers, a fast pace, general chaos—weren't leading to wins, the coach stuck stubbornly to his guns.
In Thomsen's Sports Illustrated piece, he wrote: "While college basketball is the province of marquee coaches, charismatic players dominate the NBA. Knowing when to back off and let his players play is a skill Pitino, a compulsive micromanager, has yet to learn."
The ultimate upshot of Pitino's micromanaging ways was a dangerous impatience that led to a knee-jerk trade. Boston selected Chauncey Billups with the No. 3 pick in the 1997 draft, but midway through the season, Pitino grew frustrated with the rookie's development.
So he swapped him for Kenny Anderson, a guard Pitino had admired in college and the type of player he believed would be a better fit for his style.
Anderson was a decent player under Pitino, but at 27, his best years were already behind him. Billups eventually made five All-Star Games, won the 2004 NBA Finals MVP and cultivated a reputation as one of the NBA's toughest leaders.
He would have been an iconic Celtic.
Hindsight is 20-20, but there's a reason it's practically unheard of for a No. 3 overall pick to be traded in the middle of his rookie season. Pitino overreacted, driven by his all-consuming desire to control every aspect of his team, and it cost the Celtics dearly.
Christopher L. Gasper of The Boston Globe reports that Stevens' personality doesn't include the same maniacal craving for control:
The professorial Stevens, who took Butler to back-to-back Final Fours in 2010 and 2011, has the persona of a teacher, not a taskmaster. That ability to teach and nurture is why he was one of the most respected and sought after coaches in college basketball.
Lesson 3: Forget the Press Conference
"And in [public relations], Pitino is no less polished. He makes $40,000 a pop as a motivational speaker. The last time Pitino visited the FleetCenter, it was to speak to 17,000 Amway salesmen last July."
-Alan Greenberg of the Hartford Courant on Pitino's introductory press conference, May 9, 1997.
Rick Pitino sure could work a room. Had the ability to connect with an audience, to reel them in with self-assured speech and a confident smile. Like any good recruiter, Pitino could make just about anyone fall in love with him by sheer force of personality.
When the walls were caving in around him, Pitino still commanded rapt attention. Even his meltdowns were compelling. Remember this epic rant?
What you don't hear before the clip cuts off is the following crescendo, transcribed by Allen St. John of Forbes:
All the negativity that's in this town sucks. I've been around when Jim Rice was booed. I've been around when Yastrzemski was booed. And it stinks. It makes the greatest town, greatest city in the world, lousy. The only thing that will turn this around is being upbeat and positive like we are in that locker room...and if you think I' going to succumb to negativity, you're wrong. You've got the wrong guy leading this team.
Even when he was losing, Pitino won the press conference.
But the Celtics know now that it's not enough to have a sound-bite machine running the organization. Spin only goes so far, and when things go bad on the court and everyone wants answers, there's no amount of charisma or charm that can prevent a good, old-fashioned meltdown.
Just try to imagine the mild-mannered Stevens erupting in front of the press like Pitino did. Ridiculous, right?
The Final Analysis
A couple of things have to be mentioned in closing.
First, Pitino is an indisputably brilliant basketball coach. He's a proven winner who has since admitted that he simply wasn't cut out to manage the personalities in the NBA. There aren't many coaches who'd so willingly admit to their own failings, even when said failings were so publicly obvious. Credit him for that.
And second, there are still a hundred other reasons why Stevens might ultimately be a bust. Just because he won't fail in the same fashion as Pitino doesn't mean he can't find any number of new ways to achieve the same disappointing results.
Stevens is a brilliant tactician, and has a malleable basketball mind that understands a key concept: Players dictate styles—not the other way around. Moreover, he's perfect for the increasingly analytical bent of NBA strategy and has the demeanor to relate nuanced, statistically driven information in comprehensible language.
But he's got zero NBA experience and will almost certainly have to endure a couple of losing seasons before things turn around.
If the above lessons are any indication, the Celtics haven't repeated their mistake by hiring Stevens. He's not a me-first coach, doesn't micromanage and certainly won't conduct bombastic press conferences that embarrass the team.
In other words, he's nothing like Pitino. The Celtics certainly wouldn't have hired him if he was.