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Rick Pitino, awful Celtics coach, was outdone by Rick Pitino, awful Celtics president | The Worst

- [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,

Antoine Walker.

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."

They didn't.

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

Chauncey Billups.

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.

We can't.

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,

college.

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.