Rick Pitino is no stranger to the NCAA tournament.
The legendary coach has won the event twice, once with Kentucky in 1996 and once with Louisville in 2013. With Iona, he has now only the third coach in history to take five different teams to the Big Dance.
The 15th-seeded Gaels have an enormous task in front of them facing No. 2-seed Alabama on Saturday afternoon in Indianapolis inside Hinkle Fieldhouse (3 p.m, TBS) in the Round of 64.
However, Pitino is also no stranger to squaring off against a high-powered Crimson Tide team like he did in 1987 with Providence.
Pitino and then No. 6-seeded Friars upset Alabama, a No. 2 seed, in the Sweet 16 of the tournament that year 103-82 inside Freedom Hall in Louisville, Ky. behind a team effort that saw Providence shoot 68.8 percent from the floor and 26 points and 10 assists from future Florida and NBA coach Billy Donovan.
The Friars ultimately lost in the Final Four, falling 77-63 to Syracuse. Pitino is 10-2 all-time against Alabama.
“It was really never a game,” Pitino said to the media via Zoom on Tuesday. “We blew them out. To me, looking back on my basketball life, that was one of the biggest surprises of my life that we were able to play with that team, because they were so good.
“This team, the current Alabama team, is much better than that  team on the defensive end. This team is relentless on defense. This team is not gonna allow us to shoot 67 or 68 percent, I can assure you that. We got our work cut out for us.”
Like 1987, the Crimson Tide is once again a No. 2 seed. 1986-1987 was also the last time that Alabama finished with at least 16 wins in the Southeastern Conference like it did this season.
“They had [Derrick] McKey, [Jim] Farmer, [Mark] Gottfried, [Michael] Ansley I think his name was — I can’t believe I’m remembering these names — but anyway, they had an awesome team,” Pitino added. "I thought that that Alabama team in 1987 was almost invincible. When you watch this  team — I don’t know that, I’m not an expert on Alabama basketball history — but I would probably say that team and this team are the two greatest basketball teams in Alabama history, if I had to guess. But I’m not an expert on that.”
This year's Alabama team certainly does a have case to being on the greats in program history, winning the SEC regular season title for the first time in 19 years and winning the SEC tournament title for the first time since 1991.
Per KenPom, the Crimson Tide is now up to second in the country in adjusted defensive efficiency and only allowing 69.8 points per game, while scoring nearly 80 every time out.
"They have a great system and they are fun to watch," Pitino said. "I'm not sure they will be fun to play against but they have been fun to watch on film... Anytime you have players that can put it on the floor, their 4-man, 3-man, you have to contain the basketball and rotate. They shoot so many three-point shots then you turn around and they one of the best defensive teams in the nation so it's not easy. They have so many terrific weapons and they play so hard. They are physically and mentally tough late in games.
"Alabama is every bit as good as a No. 1 seed. So it's difficult when you are a 15 seed and going up against that challenge."
When he was back in high school and knew coaching was what he wanted to do in life, Nate Oats used to watch coaching tapes of Pitino. While the two haven't formally met, the former New York Knicks and Boston Celtics coach had high praise for the man running the show in Tuscaloosa.
"I don't know him real well but he seems like a terrific coach," Pitino said. "We have a lot of respect for what he puts out on the floor and how hard they play. That's a compliment to him and his staff... I don't know of any junior or high school player in the country that wouldn't want to play in that system.
"I said to my son Richard today, 'Do you know Nate?' And he said that he's a great guy and that I would love him. I haven't had the pleasure of meeting him yet. Probably not looking forward to meeting him and his team. He's doing a great job. The Alabama program had those great moments with Wimp Sanderson in the past and now they are back."
For the Gaels to have any shot at pulling off the 17-point upset over the Crimson Tide, it begins with stifling the play of senior wing Herbert Jones, the SEC's Player and Defensive Player of the Year.
"Well there's not a whole lot he can't do," Pitino said. "He's the difference maker when it gets tough. He'll make the big defensive plays. He'll create mismatches in the low post. Just a terrific basketball player and really enjoy watching him. I love players like that. I need to recruit a few of those front court players like him. We think we are on the way to recruiting guys like him, maybe not as good right away but have that type of length and ability to play every second like it's their last second on earth."