By Mallory Evans
Medill Reports
As the auditorium lights dim, some 20 orchestral musicians pick up their various stringed instruments and begin to play lively tunes including Puerto Rico’s national anthem, “La Borinqueña.” The dream of creating this orchestra has been a long time coming.
In December, 67-year-old Orlando Rivera will celebrate 30 years as the executive director and co-founder of the Chicago Cuatro Orchestra. Based in Humboldt Park, this nonprofit organization offers free classes for anyone to learn the cuatro — Puerto Rico’s national stringed instrument — along with the guitar, tiple (a small guitar) and Latin percussion.
As a teenager in Puerto Rico, Rivera would climb to the roof of his house and sit there for hours, looking at the horizon.
“I asked, ‘What is behind that mountain?’” Rivera said. “I was always dreaming. I think that’s one of the things that kept me moving forward in everything I did.”
Rivera moved to Chicago 36 years ago for graduate school and remained in the city, though he treasured his upbringing in Orocovis and Cayey, towns in central Puerto Rico. His eyes lit up while recounting his childhood, a time when he was often surrounded by more than two dozen aunts and uncles.
“My grandparents, my uncles, my aunts — I had so much love,” he said. “That was the best thing that has ever happened to me.”
His family members worked from sunrise to sunset, ate dinner together and then walked a half-mile to collect water for the house.
“Some people today call it poor, but I call it rich, because I learned to live with just nature,” Rivera said. “And I was very happy.”
Rivera’s father played the guitar and his grandfather played the smaller tiple, which Rivera said is the “grandfather” of the cuatro. The modern wooden cuatro usually has five double strings and, depending on the register, can sound like both a guitar and a mandolin. It dates back to 16th century Puerto Rico and Venezuela, evolving from four to five strings in the late 19th century to easily create more harmonies and melodies, Rivera said.
While his father wanted him to earn a degree in a more practical subject, Rivera spent more time in the music department than studying for his business degree at the University of Puerto Rico. He decided to fully embrace music by transferring to Interamerican University of Puerto Rico in San Juan.
Rivera had been playing the double bass for years, and he soon began teaching other students at the university. Then, a graduate student introduced Rivera to a professor from the Conservatory of Music of Puerto Rico, Manuel Verdeguer, and Rivera completely “fell in love” with classical music based on Verdeguer’s own passion for the double bass, he said.
“Everyone called him ‘El Maestro,’” Rivera said. “You go to Colombia, Mexico … everywhere you go, and you say, ‘El Maestro,’ everyone knows you’re talking about Manuel Verdeguer.”
This world-renowned double bass player taught Rivera everything he knew, which eventually earned him a place at the conservatory. Rivera was “so hungry to learn” that it only took him four years to complete his bachelor’s degree instead of six. “El Maestro” even paid the remaining $200 for Rivera’s final semester’s tuition without telling him.
“(Verdeguer) was my second dad,” Rivera said. “He guided and protected me.”
While Rivera planned to pursue his master’s degree in Chicago and return to Puerto Rico to teach at the Conservatory, he realized he didn’t want to compete with his friends for one orchestra teaching position. Shaking his head with a smile, he said Chicago had been too good to him — from the city’s orderliness and calmness to its endless supply of museums, festivals and concerts. He grew up speaking Spanish and learned English when he arrived in the U.S.
After completing his master’s degree in classical music at Chicago’s VanderCook College of Music, he played in bands throughout the city whenever a double bass player was needed. But one drive home after a performance in 1995 completely altered his life’s trajectory.
“I did not know that life was holding something for me. … But that was my ‘destino,’ the will of God,” Rivera said.
Rivera’s sudden decision to change his route home to avoid traffic resulted in a drunken driver hitting his car in an intersection, crumpling it into a “ball.” Thankfully, a bongo player who played with him in the performance was driving behind him rescued Rivera and salvaged his amplifier and brand-new white bass guitar.
With a broken hand, Rivera assumed he would never play music again.
But several months later, his younger brother David Rivera — who had moved to Chicago even before Rivera had — handed him a cuatro and described his dream of starting a music program. Despite Orlando Rivera’s doubts, his brother convinced him and, little by little, he regained movement in his hand by playing the stringed instrument. His doctor, astonished by his quick recovery, encouraged him to continue playing the cuatro as therapy.
“Something negative changed my life for the better,” Rivera said.
Rivera never intended to learn the cuatro; he thought its music was too simple. But his time recovering led to a change of tune.
David spoke to a producer and arranged a practice location at the Humboldt Park Fieldhouse. The brothers began teaching classes to children in the Humboldt Park community, and in 1996, The Chicago Cuatro Orchestra was born.
“I wanted to bring the Puerto Rican community together by starting it with my brother,” David Rivera said. “It’s a family thing — parents, grandparents, all together.”
Orlando Rivera picked up a tiple in his office and demonstrated its similarities to the cuatro, tuning it after playing a quick melody. Musicians of all levels can transition between the cuatro, tiple and guitar, he said.
Orchestra members teach students ranging from 6 years old to people in their 60s.
“We see our children respecting the adults, and the adults respect the kids,” Rivera said. “Everyone protects everybody; it’s like a family.”
On Jan. 7, Rivera and his team met to discuss the future of the orchestra. Despite financial hardships in 2025 due to a lack of grants and funding for instruments and concert venues, they were determined to stay afloat. Since Rivera sacrificed hours of sleep by working last year, he decided it may also be time for a new leader.
That person might be John Rivera, a former student whose 11-year-old son now plays in the orchestra.
“Growing up, I knew the culture and music by hearing it from my dad, but I didn’t know it then like I do now,” he said. “Now, (my son) can learn about his culture without his dad just telling him.”
Orlando Rivera plans to organize a concert at Mather High School on Dec. 5 to celebrate the orchestra’s 30th anniversary, with 10 to 15 other events throughout the year. His goal: create a national cuatro orchestra festival.
“My people are such a happy group of people,” Rivera said. “Put a bunch of Puerto Ricans together, and it’s a party.”
Mallory Evans is a magazine specialization graduate student at Medill.