Mahesh Cleveland was born in Huelo, along Maui’s winding Hana Highway, and his life has followed a similar path.

When he graduated from Punahou School in 1994, the teen was one of just a handful of his 400-plus classmates who didn’t go straight to college.

“Hopefully, they didn’t consider it too much of a smear on their good name,” Cleveland said with a grin. “It sounds a little bit quaint now, but I wanted wisdom. I wanted real-world experience. I wanted to pursue my musical ambitions.”

So he played guitar and sang in a reggae band. He spent years as a carpenter, from framing houses to fine woodworking. He fathered three children and struggled to make ends meet. Finally, at age 39, he earned his bachelor’s degree cum laude from the University of Hawaii at Manoa.

Now in his last semester at the William S. Richardson School of Law, Cleveland has made his way to the top as one of 20 “Law Students of the Year” selected by National Jurist magazine, and is featured on the cover of its Spring 2018 issue.

The award highlights exceptional students who have contributed the most to their law schools and communities. It is the second time in three years that a University of Hawaii law student was singled out for the honor, following Katherine “Kaki” Vessels in 2016.

Cleveland, 42, said his willingness to try new things may have helped set him apart.

“I say yes to things,” he said. “A lot of law students are scared to take on anything extra. … Having struggled over the years, I embrace challenge a little more readily because when it comes down to it, it’s not harder than trying to figure out where next month’s rent is going to come from.”

Cleveland has tackled a wide range of activities on top of the heavy load of coursework that is typical at any law school. He helped lead Ahahui o Hawaii, the Native Hawaiian student organization, volunteered with the Native Hawaiian Rights Clinic and helped draft motions for the International Union for the Conservation of Nature World Conservation Congress.

He competed as part of the National Environmental Law Moot Court team, which won a “best brief” award; taught high school students about the First Amendment; served on the nominating committee for the State Commission on Water Resource Management; worked as a research assistant at the law school and as a legal extern for a state Supreme Court justice. After graduation, he has lined up a clerkship with Circuit Judge Todd Eddins, formerly a renowned defense attorney.

“What stands out about Mahesh is that he’s really low key and yet he’s very much a leader amongst the students,” said Ronette Kawakami, associate dean for student services at the law school. “People respect what he has to say. He’s usually very thoughtful.”

“Because of his background, he can see many different sides to issues or problems,” she added.

Cleveland’s roots are diverse. He describes his father as a “hippie lawyer” from the Midwest of Eng­lish, German and Irish heritage, and his mother as a “local girl” of Hawaiian, Chinese and Japanese descent.

Although Cleveland has focused on environmental law and Native Hawaiian rights law in law school, he now aims to go into criminal justice, with an eye toward becoming a defense attorney, likely starting at the Office of the Public Defender.

Cleveland sees that new goal as building on the ideals he expressed as a reggae singer for more than a decade after high school.

“Back then my way of questioning the status quo would be through music and writing songs and sharing thoughts that way,” he said. “But at this point in my life, I would rather try to change the law or help somebody who needs help, like directly.”

“Sometimes when you’re playing music of a certain genre, your audience is people who like that genre — I mean, you’re preaching to the choir,” he said. “Whereas taking up the responsibility of representing indigent criminal defendants, you’re not preaching to the choir. You’re actually speaking for someone before a tribunal that has the power to sort of determine this person’s life.”

Cleveland praised the UH law school for its inclusive atmosphere and for giving students like him many chances to do meaningful work outside the classroom.

“I hope that I reflect well on the school, but it’s really the school that sort of made it possible for me to get that recognition,” he said. “It’s a recognition for the school, if anything, especially considering that I’m the second in three years.”

“I can’t imagine myself having gone to any other law school,” he added. “We’re small but powerful.”