Frank Costello left the mob leadership in 1957. Bumpy wasn't released from prison until 1963. They could not have worked together.
When Bumpy is being chauffeured home from prison, there is a title that says Harlem New York 1963 and an aerial shot from behind his car that shows the entire street. Coming the opposite direction is a Peterbilt 389 dump truck. This model wasn't manufactured until 2006. There is also a modern school bus behind it and a row of present day cars parked on the street.