Maui native earns national nod as a top-20 law school student for 2018

Mahesh Cleveland said a ‘willingness to say yes to things outside of regular course work’ made the difference

Huelo native Mahesh Cleveland was recently selected as one of the nation’s top 20 “Law School Students of the Year” by National Jurist magazine and is featured on the cover of its Spring 2018 issue. CRYSTAL GLENDON photo

Huelo native Mahesh Cleveland never stopped pursuing his dreams despite dropping out of college, losing his job and barely providing for his children while attending law school in his 40s.

“There have been points in my life no matter how hard I worked there were many, many times I was scraping the barrel to pay next month’s rent,” Cleveland said Sunday in a phone interview. “But I’m used to being busy and putting in a lot of hours and having something to do next. It certainly hasn’t been easy, but I’ve enjoyed and relished the challenge.”

The 42-year-old’s effort in his last semester at the University of Hawaii’s William S. Richardson School of Law appears to be paying off as he was selected as one of the nation’s top 20 “Law School Students of the Year” by National Jurist magazine, and is featured on the cover of its Spring 2018 issue.

The award highlights exceptional students who “contributed the most to their law schools and communities in the past year,” according to a University of Hawaii news release. It is the second time in three years that a UH law student was named to the list, following Katherine “Kaki” Vessels in 2016.

“I wasn’t expecting it,” Cleveland said. “I’m not really used to being in the newspaper. It’s fun. My family is really proud, especially my mom and my sister think it’s so great. It makes me happy.”

Cleveland was born in Huelo, “right before the road gets windy,” before moving to Oahu a few years later. He would travel back and forth between the two islands through childhood and eventually graduated from Punahou School in 1994.

Unlike the vast majority of his classmates, Cleveland opted out of college and lived on Maui and in the Pacific Northwest for several years. He eventually moved back to Oahu where he attended UH-Manoa for a year and a half, but dropped out after getting married and having two children.

“I basically had to go back to work and start making money,” he said.

Cleveland worked as a carpenter for a dozen years along with playing guitar and singing in a reggae band that toured statewide in the mid-2000s. By 2011, though, he was let go in the aftermath of the Great Recession.

“It was a great job and I don’t hold it against them,” he said. “It gave me a kick in the pants. I freelanced as a handyman for a little over a year until a really good friend of mine said, ‘Dude you’re too smart to be a paycheck-to-paycheck handyman.’ “

While helping to support, now, three children, Cleveland headed back to UH and earned his bachelor’s degree cum laude at the age of 39. Later that same year, he enrolled into law school.

“When you go into law school as a first-year student, you’re starting at the bottom,” he said. “It’s nothing like undergraduate work. It’s incredibly demanding. The first year is grueling.”

Despite the heavy workload, though, Cleveland had found his dream job.

“I knew it was going to be hard, but I didn’t know it was going to be so much fun,” he said. “The learning curve is almost straight. You’re learning something new every day and that stimulates me.”

Cleveland’s “willingness to say yes to things outside of regular course work” appeared to be the difference-maker in being recognized among the top law students in the country.

“I’ll be the first to admit it has nothing to do with academics,” Cleveland said. “My grades are OK, but certainly not the top of the class. It’s all the extra-curriculars. I jumped on a lot of opportunities.”

Those opportunities included an internship under U.S. Sen. Brian Schatz; serving on the nominating committee for state water commission members for two years; sitting on the appointment committee for law school faculty; and helping to formulate internal rules of practices and procedures for the Aha Moku System.

The magazine’s editors also cited Cleveland’s work in environmental law and sustainable resource management, which included volunteering as a court reporter for Hawaii’s Environmental Court.

Cleveland’s half-sister, Danielle Sears, said she has been following her younger brother’s circuitous path to law school. Sears, who has worked as a deputy public defender on Maui for nearly 13 years, added that she was overjoyed when she heard of his national recognition.

“It’s amazing,” she said. “I was just talking to him and it was one of those things where he didn’t know where his path was, but then there it was and he just shined. He tells me all the time about all the different things he’s doing and I’m very proud of him. His big sister is very proud.”

Cleveland plans to graduate in May, sit for his bar exam in July and start his clerkship in August. If all goes well, he could be a licensed attorney before the end of the year.

The exam, however, is the “elephant in the room,” and the application has been difficult because of how many times Cleveland has moved. He said the application essentially documents your entire life, which has forced him to piece together old memories.

“I had to get back in touch with people in the past, but it’s been kind of nice touching bases with them,” he said. “Pretty much everyone in my life when they find out I’m trying to be a lawyer, they’re surprised. It’s not exactly what they thought I would do. It’s kind of fun now to wave around these articles saying, ‘See I told you I can do it.’ “

Cleveland hopes to join the Office of the Public Defender in Honolulu and gain trial experience before possibly moving into civil work. He said he would like to return to Maui and possibly work alongside his sister, which she has nudged him to do.

“Absolutely we want him” Sears said. “In a second, we would figure it out.”

Although Cleveland has been praised by his peers for his work, he credited the Richardson law school for providing opportunities to “nontraditional students” like himself. He also encouraged anyone who may think they are too old or too busy to chase their dreams — or even go to law school — and used himself as an example.

“If I represent anything, it’s that it’s never too late,” he said.

* Chris Sugidono can be reached at