Donnie Burchett sat on Summer Street in Downtown Crossing Monday afternoon, behind a cardboard sign asking for money.
Burchette, a wheelcheer bound former U.S. Marine, is one of hundreds of veterans in the city who are in need of housing.
"I don't feel like I deserve more than any other person who served," he said.
Last week, he and his buddy, another veteran who goes by "Staff Sgt. Kevin," got a taste of what it will be like this winter if they can't get housing.
"It was so cold last week (Burchett) could barely move his arms to wheel the chair so I had to push him. I don't mind - we're together until the end - but I mean, it was cold," he said.
With winter fast approaching, their story likely resonates with the roughly 6,650 men women and children in the city who are homeless.
While that number has gone down by 2.4 percent since 2010, the numbers have crept up a little in the past decade - in 2002 there were 6,210.
"The recession certainly has had an impact, but there is also an issue of poverty and high housing costs. The shelter population has grown because there is not enough affordable housing," said Director of Boston's Emergency Shelter Commission Jim Greene.
"As weather gets colder we certainly see that already crowded shelters fill up and are over capacity."
It's not an unfamiliar sight in certain pockets of Boston to see people panhandling, tugging their belongings with them, or sleeping on public property, but one place that is no stranger to people seeking refuge is the MBTA.
"We do have a number of homeless individuals who will go to our stations during inclement weather and often attempt to have conversations with them to try to encourage them to go to shelters," said MBTA Superintendent-in-Chief Joseph O'Connor.
Often times people seeking shelter will go to T stations because they are warm and dry, and there is hope of getting something to eat or drink.
"There is an attraction to South station because there are a number of businesses there for people to get coffee and have access to restrooms," he said.
There have been occasions when the MBTA has allowed homeless people to spend the night in South Station, however in those situations extra transit officers are assigned to the station at the request of the city to makes sure that "people are safe."
But in coming months, as the inevitable freezing temperatures and snow descends on the Hub, Greene said Bostonians should keep their eyes peeled for anyone in need of a hand.
"In the case of extreme weather, the best thing people can do if they see someone out in the elements is to call 911."