Chester Kaita was originally from Lahaina, Maui.
As a young man, he joined the US Army where he worked as a welder. At the end of his career with the Army he married his wife, Ruiko, and moved to Kailua on the island of Oahu.
Although Chester was a lifelong fisherman, his lure making career began in the 1960's after he suffered a heart attack, and found lure making as a relaxing hobby to occupy his time while he recuperated. He initially learned the craft through his neighbor, Sonny Rapoza. After a few months of helping Sonny with polishing and learning to pour resin from him, he began to make his own lures.
Lure making became a full scale family activity for the Kaita's. According to his son, David, who began making lures along side his father at the age of 12, Chester's wife Ruiko would pour nearly every single lure, and leave the work of cracking the molds, and then shaping and polishing the lures to perfection on a lathe to Chester and David.
Given that Chester was a very active fisherman prior to his heart attack, he began giving his lures away to friends including members of the Haleiwa Boat Club, of which he was a member, as well as captains of the charter fleet at Kewalo basin including Cornelius Choy, captain of the famed Coreene C.
He was also close friends and fishing partners with Deal Crooker, who was the principal of Punahou school at the time. Deal owned the Boston Whaler "Betty C 2" and would take his boat over to Kona each year to fish the HIBT tournament. It was through Deal that Chester was introduced to Peter Fithian who ran the HIBT, which is how Kaita lures made their way into the Kona fishing scene.
In Kona, Kaita lures gained popularity quickly and were introduced to the legendary Kona fishermen of the day, including Henry Chee. Henry began running some of the lures he received from Chester and found them to be extremely productive. So much so, that he sent a number of his original Chee lures over to Chester to have him replicate them and add Kaita inserts to the original Chee lure shapes.
Henry Chee caught his first grander on a scoop that Chester made for him which is featured in the pictures below.
Chester's most well known lures are large old school scoops made for slow trolling behind sampans, which were the boats that dominated the Hawaii fishery in the 60's and 70's. His most sought after lures are those with shell slab inserts, salt and pepper inserts and "countertop" material that looks like crushed shells.
Many of Chester's original lures were unlabeled, but after a number of impressive catches, he gained notoriety and formed an alliance with local distributor Izuo Brothers. At this point, he began adding the "Trolure" label to his creations and Izuo Brothers proceeded to market them on a broader scale.
(Source: David Kaita)