Yesterday, he challenged the monster waves at Waimea Bay and paid for it with his life.
"He died doing what he loved best," Jesse Lovett said, referring to his 28-year-old roommate, who was pronounced dead at Wahiawa Hospital after being pulled unconscious from waters near Waimea Bay about 11:30 a.m.
"The ocean was Todd's life," Lovett added.
Chesser was surfing waves 20 to 25 feet at "Alligator Rock," located between Waimea Bay and Chun's Reef.
Despite the closure of North Shores beaches yesterday due to high surf, lifeguards had a busy day.
From 9:30 a.m. to 1 p.m., jet-ski rescue operators Terrance Ahue and Abe Lerner had 18 calls for assistance on the North Shore, city Water Safety Division Lt. Mark Cunningham said.
At Makaha, jet-ski operators Melvin Puu and Jason Patterson had eight assists in 15-foot surf, Cunningham added.
A high-surf advisory remained in effect this morning for the north and west shores of all islands.
Surf in the 10- to 15-foot range is expected on Oahu's North Shore with 5- to 10-foot surf on western shores.
"It reached its peak (yesterday) but the surf is still large and dangerous," National Weather Service lead forecaster Tim Craig said.
Chesser's death yesterday shocked the surfing community.
Ron and Corrin Hill of Haleiwa considered Chesser a member of their family.
"I'm still having a hard time believing he's gone," Ron Hill said. "We called him Cheese, he always had a smile for you.
"He was such a gutsy surfer but a very caring person who always remembered to send a postcard to my wife when he was away," Hill added. "We're going to miss him very much."
Ronald "Junior" Hill and Chesser have been surfing buddies since they were 8 years old.
"He was one of the lucky guys who got paid to surf big, perfect waves whenever he wanted to," Junior Hill said. "He didn't have to do it in contests or on tour. He surfed for the love of it."
Chesser especially loved the big waves. "He waited for days like this," Junior Hill added.
"I remember a story Todd once told me about the spot he was surfing (yesterday).
"He was with Keoni Watson and said he caught the biggest wave of his life there that day," he said.
"Todd used to say surfing big waves was the best drug in the world, a natural high."
Chesser and two friends - Aaron Lambert and Cody Graham - surfed "Alligator Rock" yesterday to get away from the crowds gathering to watch the high surf at Waimea Bay.
"I heard Coby was the last one to see Todd," Junior Hill said.
"They were paddling out and a big wave was coming in. Todd stood on his board and dived in" to avoid the wave.
"When they saw he was in trouble, they went to him and tried to resuscitate him and paddle in," Hill added. "But they got caught by another set and that's when they lost him."
Lerner, one of Chesser's friends from childhood, responded to the call for assistance.
"The lifeguards saw his broken board and found Todd tangled up in the rocks," Junior Hill said.
Chesser, a Kalani High graduate, wrote articles for surfing magazines about the North Shore.
"He was getting pretty good at it and a lot of people agree that the last one he wrote, titled 'Tragic Kingdom,' was his best," Lovett said.