Prominent horse owner and businessman Robert LaPenta and Hall of Fame basketball coach Rick Pitino have enjoyed a mutually rewarding friendship for about 25 years.
It all started back in 1995 when LaPenta organized a business luncheon and brought in Pitino as a guest speaker. Quickly, they became friends and within two years the interest they shared in horse racing led to LaPenta digging into his wallet and joining Pitino's Ol Memorial Stable.
"Bob was a great partner and I became good friends with him and his son (Robert Jr.)," Pitino said. "His first wife is still best friends with my wife (Joanne). They must talk three times a day on the phone."
All the while they spent time together at racetracks, golf tournaments, and family dinners, LaPenta and Pitino would also talk for hours about college basketball, never believing their passion for the sport would one day give them a bond to match their partnership at the races.
For back then in 1997, Pitino was one of the nation's most famous and successful basketball coaches. He was the head coach of the National Basketball Association's Boston Celtics and had a resume that included winning the NCAA national title with the University of Kentucky men's basketball team in 1996.
LaPenta, meanwhile, bled maroon and gold as a loyal alumnus and proud financial supporter of Iona College, the same small, Catholic university in New Rochelle, N.Y., that became part of one of Jim Valvano's best-known quips.
While coaching at Iona before he won an NCAA title at North Carolina State, Valvano told a tale in the 1970s of introducing himself to a recruit by saying, "Hi, I'm Jim Valvano, Iona College." To that, Valvano said, the kid replied, "Aren't you a little young to own a college?"
The 75-year-old LaPenta, who grew up near Iona in Yonkers, N.Y., often credits the education he received from the college and his 1967 degree as the building blocks for a fabulously successful business career in which he is now the founding managing partner of Aston Capital. In giving back to Iona, the school named its student center after him in 2005, and more recently LaPenta's $17.5 million donation, the largest in Iona history, allowed the school to build its $38 million LaPenta School of Business that was unveiled in 2020.
Along with his $17.5 million gift, LaPenta also promised to donate another $1 million if Iona ever reaches the Sweet 16 round of the NCAA men's basketball tournament, a common achievement for Pitino and his powerhouse college teams but a daydream for a small Metro Atlantic Athletic Conference school with about 4,000 students such as Iona.
"I never envisioned Rick coaching at Iona back when we first met or talked about it with him," LaPenta said. "He was in a whole different world."
But in 2020, when the world was turned upside down by a pandemic, those two worlds became one when LaPenta played a key role in convincing his longtime friend, former racing partner, and championship-winning coach to return to his New York roots and become Iona's men's basketball coach.
A year later, that courtship has already paid a dividend as Pitino and the Gaels overcame being sidelined for about 60 days due to COVID-19 and won the Metro Atlantic Athletic Conference title to advance to the NCAA Championship Tournament and provide Pitino with one of his most satisfying experiences in a coaching career few can match. In the span of more than 40 years, the 68-year-old Pitino has won more than 800 games, made NCAA appearances with five schools, and had stints with the Celtics and the NBA's New York Knicks, but he has a special place in his heart for what happened this season at Iona.
"It's truly rewarding and a totally different experience," Pitino said about the recently completed season. "It's not professional basketball and it's not Louisville or Kentucky. It's a totally different level. But it is just as rewarding at this level as any other level and we aspire to dream and be like them. We will never fly private planes and things like that but we can certainly get the talent that they can and that's what it's all about. It's not about the coaches or the private planes. It's about who you can bring in and we're bringing in great players now."
This tale of hoops and horses illustrates how the camaraderie inherent in horse racing can be a springboard to success in other facets of life.
Long before a telephone conversation between LaPenta and Pitino paved the way for Pitino to become the Gaels' coach, the two friends were teammates in horse racing for about four years until LaPenta decided to form his own stable with trainer Nick Zito. Quite naturally, LaPenta designed his racing silks to match Iona's maroon and gold colors.
"Bob developed a real passion for owning horses," said Pitino, who now races under the RAP Racing banner. "My stable was only six or seven horses so he called me and asked if he could go out on his own. I told him 'Sure,' and then laughed and told him to be careful because there's deep waters out there."
After Pitino gave LaPenta his start as an owner, much like how 21 of Pitino's former players and assistant coaches became NCAA Division I head coaches, has enjoyed considerable success in the last 20 years. He won the 2008 Belmont Stakes (G1) with Da'Tara and the 2007 Breeders' Cup Juvenile (G1) with 2-year-old champion War Pass. More recently, the Westport, Conn., resident owned a share of 2017 Belmont Stakes Presented by NYRA Bets victor Tapwrit, 2018 Runhappy Travers Stakes Presented by NYRA Bets (G1) winner Catholic Boy , and the Eclipse Award and Breeders' Cup winners Uni and Whitmore in partnerships.
Though Pitino and LaPenta have not teamed on the racetrack since their Ol Memorial days, Pitino had a stable of about 12 horses three months ago that has been whittled down to six horses with a variety of trainers that includes Doug O'Neill, George Weaver, Cam Gambolati, and Mark Glatt.
His most recent graded stakes horse was Coach Rocks, winner of the 2018 Gulfstream Park Oaks (G2) who was also owned by Roddy Valente and West Point Thoroughbreds, and he was a part-owner of 2013 Breeders' Cup Dirt Mile (G1) winner Goldencents .
His greatest financial success came with Ol Memorial's grade 1 winner A P Valentine, who was second in the 2001 Preakness Stakes (G1) and Belmont Stakes. When the son of A. P. Indy was retired, Pitino and his partners, which did not include LaPenta, reaped a $15 million stallion deal from Coolmore, though the horse proved to be sterile.
For some of the partners, the lucrative sale was an extremely rewarding turn of events, though for Pitino it opened his eyes to the roller-coaster nature of owning Thoroughbreds.
"One of my partners, Tom Healy took his 20% share of A P Valentine and bought a beautiful home in Nantucket. Another friend, Chris Sullivan (a founder of the Outback Steakhouse chain) bought a beautiful lot in Pebble Beach with his $3 million. Another friend bought a Park Avenue apartment," Pitino said. "I put my $3 million into a horseman's account and said I would run it into $10 million or lose it all over the next 10 years and two years later I was broke."
It also illustrated how completely different college basketball and Thoroughbred racing can be.
"You have to understand how to lose in horse racing," he said. "What's a good winning percentage in horse racing will get me fired 100 times with that kind of record."
For Pitino, who spent part of his youth living in Cambria Heights near Belmont Park, the ability to share the colorful experiences at a racetrack like Saratoga Race Course and Del Mar make the sport so enjoyable and relaxing for him.
"Horse racing is like golf. It's the camaraderie of the other people," said Pitino, who has organized charity golf tournaments during his frequent trips to Saratoga. "When I buy horses, I like to take in friends so you don't get hurt too much financially and going to the races is exciting. You play a round of golf and then say let's go to the races and when you get there there's so many Damon Runyon-esque characters that you can sit back and watch them all day. You watch people yell at the TV, throw their programs. It's hysterical to watch."
What set in motion Pitino's hiring at Iona began when Pitino was the head coach at the University of Louisville, where he led the Cardinals to the 2013 national title. Amidst a federal investigation into a pay-for-play scandal at the school, Pitino and Louisville parted ways in 2017, though Pitino was never named in the charges and he has maintained he had no knowledge of any wrong-doing by staff members. Louisville was eventually stripped of the 2013 championship and 123 wins by the NCAA.
Also during Pitino's time at Louisville, the program imposed a self-imposed postseason back in 2015-16 over an escort sex scandal involving recruits between 2010 and 2014. The NCAA charged Rick Pitino for failure to monitor his basketball program.
After his departure from Louisville, Pitino then left for Greece to coach in a professional league, winning the 2019 Greek Cup Championship with the Panathinaikos team, and also guide the country's national team.
"I was happy in Greece coaching professional basketball and seeing parts of the world and great cities I had never seen before," Pitino said.
Then in March 2020 veteran Iona coach Tim Cluess stepped down after missing the entire 2019-20 season due to illness. Iona president Seamus Carey, Ph.D., had an initial talk with Rick Avare, a longtime business partner of Pitino, to gauge whether the first coach to lead three different schools to the Final Four would be willing to come back to the United States and become a college basketball coach once again.
After some initial interest was voiced, LaPenta, a member of Iona's Board of Trustees, called Pitino. In one of the Gaels' previous coaching searches, Pitino had pushed LaPenta to support the hiring of Kevin Willard (in 2007), but this time there was no third party involved in their talk. They hammered out the framework of a deal that was finalized by Carey and athletic director Matt Glovaski and on March 14 it was announced that Pitino was back in the shadow of his hometown coaching at the Division I level.
"I called Rick had a long conversation with him and he answered all of my questions the way I hoped. After that conversation I felt our stars were aligned. I made him an offer on that call to come to Iona and I'm glad we were able to get it done. I think it's going to be great for everyone involved," LaPenta said. "This will bring Iona to a national level. I really believe we could become a force in the East. I like to say with some wishful thinking that we're going to become the Gonzaga of the East (Undefeated Gonzaga will play Baylor for the national championship April 5). Rick is an incredible recruiter and his experience in managing big games is unrivaled. He's one of the greatest college coaches ever."
For Pitino, Iona's location was a key selling point in a decision that also brought him full circle to the start of his legendary head coaching career in 1978 at a mid-major program in Boston University.
"If Iona was located anywhere other than the New York metropolitan area I would have said no. But because it was a chance to go back to where it all started, I listened. They said they wanted to become the Gonzaga of the East, and I said that it will take more years than I have because it took them a good 8-10 years before they could establish themselves," Pitino said. "But we did take their model, which is taking your non-conference schedule and making it a killer schedule. Try to win your league, but if you don't, try to get an at-large bid because your non-conference schedule is so great. Bring in foreign players and transfers. It will take a long time before we reach Gonzaga's level, but we're trying to follow their model."
Taking over a team that 12-17 the previous season, Pitino and his Gaels were plagued by four different stoppages due to COVID-19 and were sidelined for more than 60 days. They finished the 2020-21 regular season with an 8-5 overall record and a 6-3 mark in MAAC play.
Seeded ninth in the conference championship tournament, the Gaels pulled off an improbable four wins in five days to beat Fairfield University, 60-51, in the title game and advance to the NCAA Tournament for a fifth straight season (there was no tournament in 2020).
The 2020-21 season ended with a 68-55 loss to the second-seeded University of Alabama in the Gaels' NCAA opener. Yet their competitive showing against one of the Top 10 teams in the country illustrated how bright their future may be with Pitino, who said he has no interest in leaving Iona for the glitz and glamour of one of the nation's premier programs.
"I got some phone calls at the end of the year from big boosters at some big schools and it was funny. When I told them I wasn't interested they took that as the offer wasn't good enough and they came up with better offers. It had nothing to do with financials. I am very much at peace with where I am at and I'm not interested in moving. I want to reach the top at Iona," said Pitino, who became just the third coach to lead five different schools to the NCAA Tournament. "Three schools would not believe it but after I called them back and said no they believe it now."
With Pitino back in the midst of the New York Racing Association circuit, it probably will not be long before he reaches out to longtime friends, like Chris Mara, whose family co-owns the NFL's New York Giants, about partnering on a horse or two.
Perhaps he'll even renew his equine partnership with his new Iona teammate.
"If Bob called me and said I need a 10% partner, I'd do it," Pitino said. "He's gotten into horse racing in a big way with some big trainers so I'd be open to it, but I'm no longer coaching the Celtics or Louisville. I'm coaching Iona, so I've taken a little bit of a vow of poverty and my percentages will have to go down."
If LaPenta and Pitino do indeed team on a yearling, there's surely a wealth of possible names but one that seems natural for them.
Gonzagaoftheeast has a pretty nice ring to it, doesn't it?
