There are two Harlequin HitMan's. They pose as the same character. Sheila and Herb (last name unknown) are old friends of Robbie Baldwin's (Speedball) parents; Justin Baldwin and Madelyn Naylor.
There are two Harlequin Hit Man's. They pose as the same character. Sheila and Herb Hollister are old friends of Robbie Baldwin's (Speedball) parents; Justin Baldwin and Madelyn Naylor.
At one point, Herb and Sheila left Springdale, working as hitmen, while posing as one person.
As The Harlequin Hit Man, they were hired by Nathan Boder back in Springdale. The Hit Man followed a chain of blackmailers who would have been able to incriminate Boder. The Hit Man would force each one to give the name of someone else who knew something. In the meantime, as Herb and Sheila, they rekindled their friendships with Justin Baldwin and Maddie Naylor.
Events led to Boder setting up a meeting with Justin Baldwin (the D.A. of Springdale) to tell him everything. The Hit Man showed up at the meeting and knocked out Baldwin when he arrived. Speedball showed up in time to save is father. Speedball knocked out the Hit Man, only to be attacked by another Hit Man. After Speedball defeated both, he left the scene and allowed his father to unmask both The Hit Men to reveal they were his friends Sheila and Herb. Both were taken to jail.
One of the Hit Men was later broken out of prison (it was never specified wether it was Herb or Sheila) alongside seven other of Speedball's earliest foes by Clyde, a man who planned to go by the name Rebound once he was able to give himself Speedball's powers. Clyde was a self proclaimed "Criminal Genuis". They planned to capture Niels the Cat who had been given the same powers as Speedball during the accident that transformed Robbie Baldwin into Speedball. It was through Niels that Clyde planned on gaining his powers. Speedball defeated eight of his foes with very little trouble.