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9:30 PM to 10:00 PM
People had begun to move away from the 125th Street and 8th Avenue by around 9:30 PM and start to break store windows. James Hughes, a twenty-four-year-old Black shoe repairer who had arrived in Harlem from Atlanta just over a year earlier, described broken glass and rocks in the street on the block between 126th and 125th Streets at this time. People saying “Let’s break windows” were on the street as he walked south toward his home on 115th Street. The Liggett’s drug store on the northeast corner of 8th Avenue and 125th Street had windows broken as did the Danbury Hat store and a seafood restaurant next to the drug store on 8th Avenue, although there is no evidence of when that damage was done. Hughes asserted that the stores whose windows were being broken around him were those "where no colored were employed." He spent enough time in the area to be equipped to make such an assessment; for seven months he had worked in the Koch department store on 125th Street between 7th Avenue and Lenox Avenue to the east. South of 125th Street, a florist and at least three vacant storefronts on the east side of 8th Avenue would also have windows broken, but there is no evidence that the damage was done at this time.
Hughes followed those on 8th Avenue going to 125th Street. By the time he arrived there were fewer people at the intersection and on 125th Street opposite the Kress store, and the sidewalk in front of the store was again cleared of people. Half a dozen police officers were in front of the store, including Captain Conrad Rothengast, who had arrived an hour earlier, and two detectives from the local precinct, Henry Roge and Raymond Gill. While Hughes was among those at the intersection, a rock thrown from across the street hit Detective Roge in the head, causing deep cuts to his eye and face. Gill, his partner, claimed that as nothing else was being thrown at the store at the time, he had been able to see a man appear from behind parked cars, look around, and throw the rock. Keeping his eyes on that man, Gill chased him through the crowd until he trapped him among the parked cars. The man Gill caught was James Hughes. Frisking him, the detective found five stones in his pockets. Hughes insisted that he had picked them up to defend himself after seeing the damage on 8th Avenue, and he had not thrown the rock that injured Roge. While Gill and officers who had been in front of the Kress store would later convince a jury that Hughes had thrown the rock, the trial judge decided that his target had been the windows of the Kress store, not the detective. That judgment was likely influenced by the assessment of a clergyman, several character witnesses and a physician from the court’s Psychiatric Clinic that such behavior was out of character for Hughes.
Meanwhile, a uniformed patrolman was assisting Roge into the alcove at the entrance of the Kress store, a scene captured by a photographer working for the ACME agency. At 10:00 PM an ambulance from the Joint Disease Hospital arrived to treat the detective’s injuries. He needed two stitches, and would spend ten days on sick leave after the disorder, but the ambulance physician recorded that Roge remained on duty.
While no windows were broken in the Kress store at this time, more shattered glass fell on the blocks of 7th Avenue north of 125th Street. The grocery store on the corner of 127th Street, first damaged at 8:45 PM, had two more windows broken by 10:00 PM. The nearby auto equipment store whose owner and staff had fled at the same time had four additional windows broken during the disorder, some likely around this time. Lazar’s cigar at the other end of the block, next to the corner of 128th Street, had its first window broken around 9:30 PM. As these white-owned businesses suffered repeated attacks, the restaurant next to the cigar, identified as having Black owners by a sign written on the window, remained undamaged.
Attacks on store windows on that block between 127th and 128th Streets spread to the other side of 7th Avenue around this time. There were far fewer white-owned businesses on the eastern side of the street, with around two-thirds having Black owners. When Patrolman Edward Doran arrived on the block at 9:45 PM he found a group in front of Sam Lefkowtiz’s store midway down the block. He allegedly saw Leroy Brown, a twenty-two-year-old Black bootblack, throw a tailor’s dummy through the store’s window, and heard him say to those with him, "Go right along and get the other windows." The unclaimed laundry store in the building to the south of Lefkowitz’s business also had windows broken, likely by this same group. They may also have broken windows in white tailor’s store in the same building; although there is no evidence that it was damaged, the dummy thrown at Lefkowitz’s store was not something that could have been picked up on the street.
The arrest made by Doran was the first evidence of a police presence on this block of 7th Avenue, the result of officers beginning to be deployed beyond 125th Street as the crowds there dispersed. However, their arrival did not stop attacks on businesses. As he took Brown into custody, Doran watched as the group of which the man had been part continued up 7th Avenue and "heard the crash of glass and later observed other windows broken." There were at least two more white-owned businesses in that section of the block, but some of those attacked may have been Black-owned businesses. The Black-owned Williams Drug Store that had its front windows broken was at the northern end of the block, on the south east corner of 128th Street. Only very recently opened, it may not have been widely known that it was a Black-owned business. The owner or his niece, the only staff member, painted “Colored Store, Nix Jack” in each of the two window panes that faced 128th Street. Those windows were not damaged.