He has a long white beard and can often be seen pushing his wife in a wheelchair along the thoroughfare.
He's also a Vietnam veteran, who served two years in the Army and has spent the past 28 years living on the street. Teresa Lyon-Nielsen, his wife, said McClure has post-traumatic stress disorder and the two have struggled to get help to get off the streets.
Since Mayor Kirk Caldwell accepted the President's Challenge to End Veteran Homelessness nearly two years ago, the U.S. Department of Veterans Affairs has assisted in housing 860 veterans on Oahu.
But 237 veterans remain homeless -- either in shelters or on the streets.
The city says there's money to house all the homeless veterans, but apartments are so limited that even some veterans with federal housing vouchers remain unsheltered.
As of last week, there were 71 unsheltered veterans on Oahu. At least eight have federal vouchers that would cover the majority of their rents -- if they could find an affordable rental.
Mike Peacock, co-founder of Hawaii Vet to Vet, said the lack of affordable apartments is one of the reasons more vets aren't housed. Another has to do with access to the VA.
"They don't make it easy," said Peacock, whose organization helps homeless veterans navigate the system.
"They have a gatekeeper mentality where you have to go through one person. If that one person is on vacation, out of the office, off island it stops our veterans from engaging with the community services that are there for them."
The VA acknowledges access can be an issue, but they're working to address the issue.
Since 2010, the number of staff members who can help homeless vets has grown from five to 54. And other steps have also been taken to bridge the gap.
"We have 800 numbers that have been created and used quite extensively. We have outreach teams that go out," said Andy Dahlburg, VA homeless programs manager.
Back on Kapiolani Boulevard, McClure broke down in tears when he talked about his frustration in dealing with the VA. Inside a bag with what few possessions they own are folders filled with papers from the U.S. Department of Veterans Affairs.
"We go out to Tripler two or three times a week and just never make any progress," Lyon-Nielsen said. "It gets so discouraging. You have no telephone contact number. You have to have 50 cents to use the pay phone. And they can't call you back. Leave a message. It's just a vicious circle,"