- [Narrator] NBA teams have hired plenty of bad coaches.
NBA teams have hired plenty of bad executives.
But no team has filled both those jobs
quite as disastrously as the Boston Celtics did
when they hired Rick Pitino.
A single decision that lead to years of wasted opportunity,
wasted talent, wasted money
and a lot more yelling than winning.
This is the worst NBA coaching hire.
May 6th, 1997, Boston, Massachusetts,
Rick Pitino is introduced to fans and media
as the next head coach and president
of the Boston Celtics
after receiving a record setting
10-year, 70 million dollar contract.
Going all out for Pitino was a bold choice
considering the alternatives.
The Celtics won just 15 games in 96-97
and coach M.L. Carr stepped down at season's end.
Boston had two lottery picks in the upcoming draft
and needed someone to lead this rebuilding team.
They had options, just to name a few,
Larry Brown was a free agent after leaving the Pacers
but he ended up with the Sixers for a while.
Title winning icon Chuck Daly
was considering coming out of retirement
but he ended up doing so for the Magic.
Or this guy, Larry Bird is a Celtics legend,
had been acting as special assistant in Boston for years
and wanted to become a head coach, which he did,
Bird won Coach of the Year in his very first season
with the Pacers.
The Celtics preferred Pitino.
Preferred him so much in fact,
they were willing to demote another Celtics legend,
Red Auerbach himself to secure Pitino's secondary role
as team president.
Pitino did what he does best in this press conference.
It's what he was doing the last time he visited this arena
for an Amway salesman conference, smooth talk.
Buttering up a crowd by saying just the right thing.
Pitino was and is elite at that.
- Uncomfortable, no.
I'm uncomfortable and humbled sitting below these banners.
But I'm very excited to contribute
to the raising of another one.
- [Narrator] But it's not like Pitino
was unqualified for the job.
In the 80's Pitino jumped from a Final Four team
at Providence to the NBA,
where he helped turn around the Knicks.
Then he jumped right back to college
highlighting and eight year stint at Kentucky
with an NCAA Championship in 1996.
His star on that team
was the first young star he'd coach in Boston,
But before he could coach,
Pitino would have to do some managing
because that was his job too.
He traded for a GM, Chris Wallace,
and the two of them started planning
for the NBA Draft where they had those two lottery picks.
Unfortunately, the lottery was not as kind to Boston
as Pitino hoped.
Or hoped might not even be the right word.
Flash forward to the year 2000
and you'll find Pitino saying,
"The thing that attracted me here
"was the thought that we were going to get Tim Duncan."
That was an outcome with about a 38% chance of happening.
But to quote Pitino, "If that failed,
"it was almost 50% we were going to get the number two pick
"and Keith Van Horn."
The lottery machine spat out
picks number three and six for Boston.
Pitino's first thought was to ditch the picks
and then trade for Scottie Pippen
but the Bulls ultimately said no.
Draft night arrived and Duncan, the clear number one choice
and one of the greatest players ever
would go to another coach slash executive,
Greg Popovich and the Spurs.
The coveted Van Horn went number two as expected
and Van Horn actually got traded
but not before Pitino tried to interfere
by filing a protest with the league.
But Pitino's Celtics were still in great shape.
They could've done way better than Keith Van Horn
if they'd capitalized.
With the third pick, Boston snagged Colorado's
We'll come back to him.
The sixth pick?
Pitino made a big show of desiring high school phenom
Tracy McGrady, but it was all a smokescreen
for Pitino's real target, Ron Mercer,
his own Kentucky shooting guard who wasn't very good at,
you know, shooting.
McGrady went ninth to the Raptors
and later became a superstar
Anyway, besides the draft,
Pitino the president had a lot of team to build
for Pitino the coach.
In July, Pitino signed medicore tall man
Travis Knight to a seven year, 22 million dollar deal.
Knight neither expected nor really wanted
to become a Celtic,
but couldn't resist such a long contract.
To make room for signings like Knight
and fellow mediocre tall man Andrew DeClercq,
Pitino renounced rights to all nine of Boston's free agents,
including Rick Fox who'd become a starter
on multiple Lakers championship teams.
Knight would also win a championship with the Lakers
after Pitino traded him a year and a half into that contract
for mediocre tall man Tony Battie
who they signed to an even pricier contract.
Making moves then undoing them
became a signature of Pitino's presidency.
In August of 97, the Celtics signed Chris Mills
to a 34 million dollar contract.
Then they traded Mills to the Knicks
before he'd even played a game in green.
Around the same time,
Pitino dealt Eric Williams to the Nuggets.
Williams would tear his ACL
days after his Nuggets debut
and then Pitino's Celtics would reacquire him
two years later for a package
that included 1997 draft pick Ron Mercer.
The man loved to make deals.
Just ask Antoine Walker,
who watched the roster around him
flip several times over.
Pitino had a complex relationship with Walker,
his former Kentucky star.
It went relatively okay,
give or take Walker skipping
voluntary summer workouts.
One of several times Pitino openly criticized
his temperamental star.
He considered trading Walker a few times too,
but Pitino spoke proudly
and honestly kind of condescendingly
about how he related to Walker.
On that note, let's see how Pitino coached
his prized third pick, Chauncey Billups.
The very first game of Pitino's Celtics tenure
was a rousing victory over the defending champion Bulls.
Walker lead the team in scoring
and Billups played terrifically in his debut off the bench.
After that, disaster.
Billups was meant to be Boston's point guard of the future,
an important player to develop.
Pitino handled that by screaming at Billups so much
that he was constantly looking over his shoulder
on the court and complaining about Billups in the media.
Then, 51 games into Billups' career,
Pitino traded him away for the declining Kenny Anderson.
Billups would one day develop into a regular all-star,
a Finals MVP, and probably a Hall of Famer,
but as a rookie Celtic, Pitino deemed him
not my kind of point guard.
The creepily paternal college style approach
showed up everywhere in Pitino's coaching.
He insisted on playing a full court pressing defense,
the kind of thing that works with kids
but drains NBA players over an 82 game season.
To quote Bill Simmons,
Pitino was slowly sucking the life from his players.
And just like in college,
Pitino expcted to be a star himself.
Dee Brown, one of the many players Pitino dumped
from Boston's roster described him as a me person.
The 98 Celtics won just 36 games,
so that summer Pitino the president got back to work.
Boston did great in that draft
when Paul Pierce fell into their lap with the 10th pick.
Pierce had an excellent rookie year,
the Celtics got worse
and they didn't get to make a first round selection
in the 99 Draft because Pitino traded the pick for
mediocre large man Vitaly Potapenko.
Cleveland ended up using that pick they got
on future league assist leader Andre Miller
while Boston still had the aging Anderson at point guard.
The next season, Boston still failed to match
the 36 wins they'd gotten in Pitino's first year.
In March of 2000, the Raptors beat the Celtics
on a Vince Carter buzzer beater
that was assisted by the way by McGrady,
the guy Pitino passed on for Ron Mercer.
Anyway, the smooth talking Pitino
didn't sound so smooth after the loss
and this diatribe would go down in history.
- Larry Bird's not walking through that door, fans.
Kevin McHale is not walking through that door
and Robert Parish is not walking through that door.
And if you expect them to walk through that door
they're going to be gray and old.
I wish we 90 million on the salary cap.
I wish we could buy the world.
The only thing we can do is work hard.
- [Narrator] Keep in mind that all but a couple players
on Pitino the coach's roster
were put there by Pitino the president.
But by the following season,
Pitino was openly talking about leaving
and admitting that this job has turned out
to be tougher than I thought.
In January of 2001 with a season record of 12 and 22,
Pitino quit, forfeiting a massive amount of money
to return to the life he knew best,
A world where coaches are stars,
players are used to getting screamed at,
press and trap defense works
and instead of managing a salary cap
you can just do scandals.
By the way, Pitino's assistant coach, Jim O'Brien,
took over as an interim
and went 500 the rest of that season.
Then the very next year,
he took Boston to the Eastern Conference Finals.
And of course, Pierce later won a ring
as part of a well constructed and well coached Celtics team.
These days, it's clear that transitioning
straight from college coaching to the pros is difficult.
There are success stories,
but many more failures.
It's equally apparent that being a coach and executive
is a lot to ask of one person.
Again, there are exceptions,
but it goes wrong more than it doesn't.
But in 1997, the Celtics attempted all of the above
all at once.
They hired a college guy to be their coach and president
ignoring way better options
including one right in their lap.
Doing so set the franchise back years.
They blew opportunities to develop quality guards,
blew millions of dollars on mediocre tall men
and tested the patience of multiple stars.
The Celtics tried to kill two birds with one stone
but it was a very crappy stone
and they only killed themselves.