The Brooklyn man pleaded guilty to a violation after spending a night in jail, but he later appealed. Courts have upheld his arrest so far.
His lawyer, Nancy E. Little, said Wednesday there was no legal justification for arresting Jones for simply standing on the street.
"You need something more," she said. "You need to be being verbally abusive, or really blocking lots of people, or lying down on the sidewalk."
But assistant Manhattan district attorney Paula Rose-Stark said the disorderly conduct arrest was warranted, noting that Jones' behavior stood out "amid the inevitable hustle and bustle of Times Square."
Prosecutors' arguments drew several questions Wednesday from judges — including Chief Judge Judith Kaye, who wondered aloud how bustling Times Square was when Jones was arrested around 2 a.m.