From Hawai'i to Iona, Rick Pitino's Coaching Legend Continues to Grow

If you tune into Friday night's Iona vs. UConn NCAA Tournament first round matchup, you'll see a familiar face - and slicked back hair - stalking the sidelines. He's coached in the Big East, the SEC, the ACC, the NBA, and even the Greek League. His resume includes seven Final Four appearances, a handful of scandals, a few ignominious departures and multiple teams coached. We are, of course, talking about Rick Pitino.

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The 70 year-old Pitino is a legendary figure in basketball. His career spans six decades and includes success - and raised eyeballs - at every level of the game. 

Early Rick's Rise

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Going back to his first job as a graduate assistant and eventual interim head coach with the University of Hawai'i from 1974-1976, Pitino faced allegations of skirting NCAA rules. Apparently he was accused of providing roundtrip airfare for players between NYC and Honolulu, handing out McDonald's coupons, and arranging for players to get used cars. Couple of questions about these allegations, which seem so quaint and tame by modern standards: how much was airfare between Honolulu and NYC in the mid 1970s and how on earth could Pitino afford it on an assistant coach's salary? Did the Rainbow Warriors have some incredible booster making sure its players got paid? Also if they did - it didn't work. Hawai'i was really bad. 

After a brief stint serving under Syracuse head coach Jim Boeheim, Pitino was hired to take over the Boston University program. It was at BU that Pitino made his first NCAA Tournament experience, getting the Terriers to use a full-court press for the entirety of every game. Which, if my middle school basketball experience and "Coach Carter" is to be trusted, must have made for absolutely terrible practices. 

The Final Four and The NBA

Pitino's first dalliance to the NBA came in 1983, when he took an assistant position under Hubie Brown of the New York Knicks. It was a return home for the New York and Long Island native, though a short-lived one, as just two seasons later he bounced for the head coaching position at Providence College. At PC he resuscitated a dead program. The 1986-1987 season was the introduction of the three-point line in collegiate play, and Pitino's Friars, led by guard Billy Donovan, really leaned into the concept. They shot their way all they to the program's first Final Four appearance since 1973. It was the first taste of the national spotlight for Pitino, and at just 34 years old, it was clear Pitino would have a long career ahead of him. 

Just after he signed a five year extension with the Friars, Pitino went back to the Knicks, becoming their head coach in 1987. The 88-89 Knicks won 52 games in the regular season before bowing out to the Chicago Bulls in the second round. Following the '89 season, the Kentucky job became available, as their program was embroiled in a recruiting scandal. Pitino, who had just coached his hometown NBA team to a 52 win season and had young star center Patrick Ewing on his roster, openly discussed leaving for the Wildcats position. As reported in The New York Times, he met with Kentucky officials and even told the press that ''There's a lot I like about [Kentucky]...The big question is do I want to give up the Knicks.''

Rick Heads Back to College, Then Back to the NBA

Well, turns out he was okay with leaving the Knicks, because shortly thereafter Pitino was on his way to Lexington. 

As he did at BU and PC, Pitino brought the Kentucky program back to life. The difference this time was that he wasn't bringing a small New England school back to relevance; this was Kentucky. One of the true blue bloods in college basketball. And as soon as he started winning, he became incredibly popular amongst Kentucky fans. 

Pitino's 90s Kentucky teams played fast, played aggressive, and won big. Jamal Mashburn, Tony Delk, and Antoine Walker were just a few of the standouts Pitino coached in his time at Kentucky. His teams made three Final Four appearances, and won the national title in 1996. 

It's interesting to consider a different road for Pitino at this point. What if he had just stayed in Kentucky? Is there a chance he would still be coaching the Wildcats today, finishing up his 33rd season, making his 30th (ish) appearance in the NCAA Tournament? He had the pinnacle of positions in college hoops and was winning at the highest level. Why not stay and become a Lexington legend?

Because that's not how Rick Pitino is wired, baby! In the spring of 1997, Pitino jumped ship to become the head coach, general manager, and president of the Boston Celtics. 

Hindsight being 20/20, this was a terrible move for all parties involved. But at the time, Pitino was considered one of the best basketball minds in the world. He had won in the NBA before, and had a good feel for how the game operated. So what went wrong in Boston?

Well, pretty much everything. Pitino went 102-146 in his Celtics tenure. And while that's not exactly a stellar record, it could have been forgiven if the front office moves made any sense and the team was moving in the right direction. But that was all terrible as well. Pitino made a number of head-scratching moves as the Celtics GM, the worst of which was trading Chauncey Billups just 51 games into his career after selecting him with the No. 3 pick in the NBA Draft. 

The highlight of Pitino's Celtics tenure was probably that rant. Just a brutal experience for Boston fans and Pitino fans alike. 

Rick Heads Back to Kentucky (Kinda)

Following that disastrous adventure, Pitino went back where he felt more comfortable - college basketball in Kentucky. This time, it was a different part of Kentucky. Louisville. 

It is so deeply Pitino to take a job for his former school's in-state rival. 

It is also very Pitino to win a whole lotta games for said in-state rival. 

Under Pitino's helm, the Cardinals went to three Final Fours and won one national championship in 2013. They made the jump from Conference USA to the ACC. He took a historically strong program and turned it into a juggernaut. 

And then a number of scandals tore it all apart. First there was the personal sex scandal for Pitino. In a very ugly situation, Pitino admitted to having an affair, but the woman in question, Karen Sypher, was eventually sentenced to seven years in prison for extortion and lying to the FBI. Unscrupulous readers (like this writer) may remember Pitino's testimony that the sex happened in an Italian restaurant, lasted for 15 seconds, and was unfortunate. Yeah. Unfortunate seems like the correct word choice. 

In 2016, a former escort accused a Louisville basketball assistant coach of paying prostitutes to dance for and sleep with Cardinal basketball recruits. Not great! But Pitino slithered out of that one. 

The next year, though, the levy broke, as the FBI got involved with various allegations of pay-for-play in the college basketball world. Slimy characters abounded. There were allegations about improprieties within the sneaker world, the AAU circuit, the world of agents, managers. Just skeezeballs everywhere.

The Louisville program was extremely involved, and it spelled the end for Pitino's coaching career. 

What's Next for Rick Pitino?

Except, obviously it didn't, because Pitino is back, baby!

Some people are born to do a certain thing. And for Pitino, that thing is to coach basketball and yell. 

When his stateside career seemed over, Pitino took a job coaching in the Greek League. What did he do there, you ask? Well, he won a title. And probably lots of other shady shit. But he showed that he can still coach ball. 

Because the collective memory of college basketball programs is incredibly short, Pitino received an offer to coach at Iona in March of 2020. He has led the Gaels to two NCAA Tournaments in three seasons, and they enter Friday night's matchup as a trendy upset pick over UConn. 

Thursday morning, Pitino met with reporters who asked him about his future. According to Rick, he'd like to coach for ten more years. Asked where he would do such coaching, he responded, "So to answer your question that would be honest, it's going to take a special place for me to consider leaving." 

Reports and rumors have linked Pitino to the St. John's job. It would be a return to New York City, a return to the Big East, and another opportunity to revive a once proud but recently moribund program. I can already hear him doing weekly interviews on WFAN, and see him on the back page of the NY Post once a week.

Sounds like exactly the type of "special place" for Pitino's next chapter. 

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