Any performer will admit that it’s nice to have fans. But what if your biggest fan is President Trump?
Christopher Macchio is an opera singer from Long Island, New York. Through a series of fortunate events, he has found himself at the White House, at Mar-a-Lago, and various Trump properties, where he has performed for Trump and his family upon request for several years.
Trump loves Macchio’s voice so much that he—or someone in his administration—bestowed Macchio with the moniker, “America’s Tenor.”
How did Macchio go from being an unknown in middle-class suburbia to being a repeat performer at the White House?
A Reluctance to Sing
Believe it or not, as a child in Holbrook, New York, Macchio had no interest in music. He said he “was all about academics at first,” while enrolled in Sachem High School’s gifted program and advanced-placement classes. In 10th grade, he chose chorus “to satisfy a New York State Regents diploma requirement.”
“I had no interest in performing or letting anybody know I could even carry a tune,” he said. He felt chorus would be “a relatively anonymous way to fulfill that requirement.”
The plan fell apart when his chorus teacher, Mr. Gerstenberg, said each student needed to sing a solo in front of the class. Macchio refused.
After class, Gerstenberg pulled Macchio aside and insisted he sing. Accepting defeat, Macchio sang “Try to Remember” from the off-Broadway musical, “The Fantasticks.”
Gerstenberg could not believe the voice that came out of this 15-year-old. He ran to a file cabinet and frantically pulled out sheet music and started playing the songs on a piano, asking Macchio if he knew each of them.
“At the end of it, he just sat me down and said, ‘Christopher, what exactly do you have planned for your life?’ and I said, ‘Well, I’m going to be practicing law or medicine. Probably law,’” Macchio said.
“And he said, ‘That’s the wrong answer, son.’ He goes, ‘I’ve been teaching for 27 years and I’ve never had a voice like yours come through. You have a gift; you have to share that gift. A gift from God that has to be shared.’”
A New Path
Macchio knew he was right, and Gerstenberg facilitated Macchio’s placements in the All-County and All-State Choruses. And at the end of the school year, when Gerstenberg said he should attend a summer camp for fine and performing artists, he took his advice again.
Macchio auditioned for “all these muckety-muck types” at Usdan Summer Camp for the Arts on Long Island. “They had no expression. It was a poker face,” he said.
His mother received a call the next day and the representative from the camp said how impressed they were and wanted Macchio back to sing for Andrew McKinley, the 90-year-old founder of the camp, whom they would bring from New York City.
McKinley was a Metropolitan Opera singer, and he would help them decide “what besides just letting him into the camp” they could do to help the young man.
Not only was Macchio accepted to the camp on a scholarship, but the administrators set up weekly private voice lessons for him with John Kuhn, another retired Metropolitan Opera singer. These lessons lasted through the summer and through his junior year in high school.
After high school, he earned a degree in political science and history from Stony Brook University on Long Island, followed by a stint as a salesman for Armani suits.
However, Macchio kept one foot in music by continually taking voice lessons from Kuhn, plus one recital per year.
In 2010, at the age of 32, he auditioned with four other singers as a group for a PBS/EMI Records production in New York City. “The audition was a disaster. It went horribly. We did not sound good together at all,” he said.
Later that day, Macchio retreated to Kuhn’s Manhattan apartment with “really thick, pre-World War II walls,” which blocked his cell phone signal.
When he emerged hours later, he had 10 voicemails. “They basically said, ‘Christopher, we love your voice; we just want you,’” he said.
At this time, Macchio was getting his ducks in a row to apply to law school, and called getting cast in this television special “the turning point” in his life. “Here I was applying to law school, ready to give up the whole thing,” he said.
In the National Spotlight
Macchio’s first performance for Trump was before his foray into politics.
On Dec. 30, 2014, Macchio received a call from an employee of the Trump Organization. He said Elton John had just canceled his performance at Mar-a-Lago’s New Year’s Eve party, and Trump wanted a “big name to sing a few songs to really blow everybody away”; the employee said he knew a guy. Trump gave him his blessing to book Macchio, who would sing with the house band.
“It was a thousand people in the ballroom at Mar-a-Lago. So I sang three songs,” Macchio said. He received a standing ovation and compliments from Trump following the performance.
A few years passed and Macchio was performing at charity concerts in Millbrook, New York. “The owner of the venue that was hosting these charity events was the wife of Robert Trump [Donald’s brother], Anne Marie Pallan,” said Macchio. “He became a really big fan.”
Robert Trump passed away in 2020. Pallan was at his hospital bedside and moments after his death, called Macchio. He said she said to him, “God just told me that you need to do the music for his funeral. Can you do it?”
The two-and-a-half-hour funeral was held in the East Room at the White House, and Macchio performed 10 songs.
The fifth song in the set was to be “The Lord’s Prayer,” which is the “Our Father” prayer set to music. He told the event coordinator that the song ends with a big climax, and he was concerned that it wasn’t appropriate for a funeral.
She said, “The bigger you do it the better.”
“So I took that advice to heart, I did it really big, and the president jumped out of his seat in the middle of his brother’s funeral and gave me a standing ovation,” he said.
Trump booked Macchio for the following week to sing at the White House on live television when he would accept the Republican nomination for the 2020 presidential election.
A Difficult Gig
When the day came, things didn’t go smoothly at first. Trump’s plan for Macchio was for him to sing after the speeches, as a big finish. But the RNC had other plans and insisted he sing before them.
While he was singing at the start of the event, people were still filing in, and television reporters were talking over him. “I gave everything I had because I thought that was my one shot,” Macchio said.
He sat on the south lawn next to television host Laura Ingraham and journalist Raymond Arroyo, listening to the speeches. The Secret Service approached him and said he needed to “come with [them]” back into the White House. At first, Macchio thought he was in trouble, but then an agent said, “The president is going to need you to sing all the music again after his speech.”
“I’m spent by the way,” Macchio said. “I spent all the voice that I had had on the first go-around,” which included several hours of rehearsal in the 95-degree D.C. heat and humidity.
At the last minute he was told he’d sing “one or two songs,” which he and a few musicians would perform from a balcony.
“As soon as I started singing, the president goes to the family, they turn around at his direction, and they all line up and they just look up at me, all of them in single file, and they patiently listen while I do the whole of the music over again—20 minutes!”
Macchio’s popularity within the Trump orbit reached its peak when two separate entities wanted him in two different places on election night in 2024. One wanted him at Mar-a-Lago for dinner, and the other wanted him at the convention center, ready to sing if Trump were victorious.
Macchio chose the convention center and was ready to go with a Trump favorite, Nessun Dorma (an operatic song about victory).
The election was called for Trump later than expected, and Macchio, Lee Greenwood, and the other performers were cancelled. But a few weeks later, there was a victory party at Mar-a-Lago where he got to perform.
“And that one went viral because at the end of my performance, right in front of me was President Trump and Elon Musk, and I pulled both of them on stage with me and the three of us sang ‘God Bless America together,’” he said. Macchio was flanked on either side by them and, at the end, grabbed their hands and raised their arms in victory.
On another occasion, Macchio met with the president in the Oval Office. He was in there a few minutes before Trump arrived. “I’m walking around; I’m feeling the pillows on the couch,” he said. After Trump arrived and sat at the Resolute desk, he arranged for Macchio to perform at The Kennedy Center.
The Future
Trump has more plans for Macchio in 2026. He’ll be performing for the country’s 250th birthday celebration throughout the year and at the opening of “The Big, Beautiful Ballroom.”
The Trump family has given Macchio opportunities other performers could only dream of. How did this kid from Sachem High School—who was too intimidated to sing one song in front of his chorus class—feel walking around the Oval Office, poking the pillows?
“It has served me well to remain humble throughout whatever has occurred to me from a career standpoint,” he said. “And it’s easy to maintain that humility when you remember that whatever gifts that you might have that got you there were endowed by God. So I really look at all of this as responsibilities that I’ve been entrusted with. Opportunities that should be put to some greater purpose.”
Mr. Gerstenberg was right.
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