Charles "Chuck" Pennington is Daniel's father, and April's boss in the first film. He had trouble dealing with his son, who had a problem with stealing, and was unaware that Daniel had joined the Foot Clan.
Charles was blackmailed by Chief Sterns that if he could get April to back off on the mysterious crimes caused by the Foot, then his son would not get into trouble. He told April to not "push anymore buttons", but of course April was persistent. He later received an angry phone call from Sterns yelling "Pennington, I thought we had a deal!"
Later, Pennington called April to tell her that she was fired. However, her house was attacked and burned by the Foot Clan. (Though, Casey heard the answering machine and eventually told April.)
When April came back to New York, Pennington told her of the consequences and that he wanted her back. April, after easily getting her own corner office and receiving higher pay, sarcastically and rudely told him he was "a tough negotiator." Pennington appeared to brush off the comment, more focused on his reunion with Danny.