by Jim Fenton, The Enterprise
His basketball coaching career began during the 1990s at Brockton High School and Massasoit Community College.
Orlando Vandross was a recent graduate of American International College and was teaching health and physical education in Brockton when he began exploring the world of coaching.
First, the 1987 Brockton High graduate was a volunteer assistant on head coach Victor Ortiz's Boxers' staff in 1995, then he moved over to work as an assistant for head coach Mark Ottavianelli at Massasoit in the 1996-97 season.
Those were the first steps taken by Vandross that have led him to the opportunity to coach in the Final Four of the NCAA Division 1 tournament this weekend.
Vandross will be on the bench in his role of assistant coach at the University of Virginia when the Cavaliers take on Auburn in the semifinal round Saturday at 6:09 p.m. at U.S. Bank Stadium in Minneapolis.
"I got an unbelievable beginning with coach Ortiz and Mr. (Bob) Boen (the former Brockton assistant and now head coach of the Boxers),″ said Vandross this week from Virginia. "They gave me a shot. I could never thank them enough. I'm always grateful.
"Then I went to Massasoit and worked with Otto and he gave me a chance and it was just a great experience.″
Vandross, who was inducted into the Brockton Hall of Fame in 2003 for his achievements on the basketball team in the 1980s, is in his fourth season on the staff at Virginia.
He worked as the director of recruiting and player development for three years before becoming an assistant coach to Tony Bennett this season.
The Cavaliers are making their first trip to the Final Four since 1984, when Vandross was a freshman at Brockton High.
"It's unbelievable,″ said Vandross. "That's all I keep coming up with.
To do it at this time, with this team and coaching staff, it's just unbelievable.
"It's hard to put this all into words. These are the four best teams. It's the equivalent of the Super Bowl, the World Series, but at the collegiate level. This is where every coach wants to be. I can't wait.″
After his one season at Massasoit, Vandross joined the coaching staff at Boston University and spent 13 years on Commonwealth Avenue, then had a five-year stay at the University of North Carolina Charlotte before joining the staff at Virginia in the summer of 2015.
Through the years, Vandross would make trips to the Final Four and think about one day working on the sideline in the biggest weekend of the college basketball season.
"I would go to the Final Four practices on Friday, which are open to the public,″ said Vandross. "I'd sit there and I'd see friends who were part of it and I'd say, 'I wonder what it's like to do that? I'd really love to be down there on the floor.'
"Now I'm getting the chance to live that dream.″
Vandross said that his father, David, and brother, Ortez, who both live in Brockton, are among those who will be on hand in Minneapolis for the Final Four.
There will be a number of others with connections to Vandross who will be pulling for Virginia to win the national championship on Monday night.
"I'm happy for him,″ said Ortiz, his former Brockton coach who sent along congratulations to Vandross this week. "He's a very unpretentious guy. I'm proud of him. He worked for everything that he got. Nobody handed him anything along the way.″
Ottavianelli, now the athletic director at Taunton High School, was also in touch with his former assistant after the Final Four berth was clinched.
"He's just a fantastic person,″ said Ottavianelli. "We've been great friends ever since that year at Massasoit. I am just so happy for him to have an opportunity like this, to coach in the Final Four. I'm thrilled for him.″
Vandross was part of Brockton High's 1985 state championship team that went 24-1, playing a reserve role as a sophomore.
He was the starting point guard the next two seasons and was elected captain as a junior and senior before moving on to AIC, where he ranks third in career assists and 13th in scoring.
"He was very intense as a player, the best defensive guard that I coached,″ said Ortiz. "He could score, but he was unselfish. He was a rare kid, very intense but he kept his composure.
"He was a leader. You put the ball in his hands. He challenged kids. That's what made him exceptional. He was quiet, but he wouldn't back down.
"I told him that he was an extension of me on the court. Two-year captains didn't happen very often at Brockton High, but there was no question who the captain would be.″
When his playing days were finished at AIC, coaching was the natural next stop for Vandross, and those early days at Brockton and Massasoit got Vandross going.
"Right away, you could tell he was going to be good,″ said Ottavianelli. "He is a quality person and a quality coach. He had great relationships with the kids. I knew he wasn't going to be staying long.″
From those days of riding the buses with the Brockton High team and taking vans to road games with Massasoit, Vandross is fulfilling a dream by coaching in the Final Four.
"It's kind of funny,″ said Vandross. "After the game (last Saturday, an overtime win over Purdue in the regional final), I was not able to sleep. Now I've been working to get ready for this weekend. It'll probably hit me when I walk into that dome.″