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The tall, red-and-yellow neon sign is hard to miss driving down Kapahulu Avenue in Honolulu, on the Hawaiian island of Oahu. A large arrow points to Hawaii’s long standing icon Leonard’s Bakery, where lines wrap around the front and a mountain of malasadas — 8,500 of them — are sold every day. It’s become a malasada landmark owned and operated by generations of Leonards.
Best eaten hot and fresh, the pillowy-soft Portuguese doughnut is covered with sugar and shaped round without a hole. No one knew back when the bakery opened 70 years ago that malasadas would become so popular.
“The bakers didn’t want to do it,” Crystine Ito, Leonard’s Bakery’s marketing manager, told SFGATE. “They said it was too ethnic, too different, but they didn’t own the bakery.”
Portuguese immigrants brought the malasada to Hawaii at a time when immigrant workers around the world were being contracted to work in the sugarcane fields around the late 1800s, but Leonard’s Bakery was the first bakery to make the sugary dessert widely available.
Leonard Rego was the grandson of Portuguese immigrants from the Azores’ Sao Miguel Island who were sent to Maui to work. Rego moved with his wife, Margaret, to Honolulu and worked as a manager at another bakery before opening his own. In 1952, he opened Leonard’s Bakery and then, needing a bigger space, he moved the bakery to its current location on Kapahulu Avenue in 1957, and brought the neon signs with them.
Selling breads and pastries, the bakery boasted “the finest of bakery products,” using natural ingredients of island eggs and fresh milk, unlike its competitors, who used powdered eggs and milk.
It was Rego’s mom who suggested making malasadas using her own mother’s recipe not long after opening. A Portuguese tradition, she encouraged Rego to make them for Shrove Tuesday, or Fat Tuesday, which falls the day before Ash Wednesday — and is the last day of eating rich foods before fasting for Lent.
“We’re just such a melting pot, and everyone always uses that phrase because we truly are, and I think they accepted a Portuguese dessert in Hawaii and it took off,” Ito says.
Technically, malasadas are from the Azores islands, an archipelago off the coast of Portugal. The confection is made with yeast, eggs, butter and milk, but there can be variations in the recipe. Leonard’s Bakery uses their family recipe. Its secret is in how the dough is made, and it’s still in use today.
The bakers, some of whom have been there for more than 40 years, mix over a thousand pounds of dough daily. From beginning to end, it can take about three hours.
“The process is really long,” Ito says. “They put all the ingredients together and they do the first mix and then they mix it again. They let it sit, they pull it out, they let it rise. They have to cut the dough, they fry the dough.”
Leonard’s also makes pao doce (Portuguese sweet bread), pastries, cookies, cupcakes and pies. In the 1960s, the bakery was the trendy place to go to get custom cakes — decorating as many as 250 cakes on the weekend. It most notably created elaborately designed birthday cakes for celebrity parties, such as the ones for Duke Kahanamoku and Bob Hope.
When Rego’s wife passed away, their son Leonard Rego Jr. became the current owner and decided he wanted to continue the legacy his parents had started. Today, his kids, including another Leonard, have helped with the bakery, too.
Though the family would love to keep Leonard’s Bakery in the family, it has never been a requirement.
“They never actually made their kids come back to work,” Ito says. COVID-19 brought the youngest Leonard back to Hawaii from college. “While he was here, he learned the family business and worked in the bakery. … I think he’s enjoying it.”
The original malasada is still the bakery’s best seller, though some are now sold with a variety of fillings. In the early ’90s, Leonard Jr. thought filling the doughnuts with creams, such as custard, dobash (chocolate) and macadamia nut, would be a nice complement. The custard filling is customers’ favorite.
The bakery has also grown to five Oahu locations. Four of them are food trucks scattered across the island, called Malasadamobiles. In 2005, a franchise location opened at a four-story shopping complex in Yokohama, Japan.
“[Leonard Jr.] just feels like it’s the hard work and his team’s commitment to the bakery that makes them successful,” Ito says. “When you think of Hawaii, a lot of people think of plate lunches and malasadas, so I think he really does like being part of Hawaii’s culture.”
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