Harry was a sleazy attorney who first sued Sydney Andrews while representing Hilda Morris. His loyalties were only to his client and not to the truth. In fact, he encouraged Hilda to do more things that would get her more money out of the lawsuit.
Later, after winning the case, he approached Sydney and told her he could help her win a lot of money as well. He schemed with her to have her fall at the D&D offices so that she would sue and win a ton of money from them.
After she fell and attained actual injuries, Harry kept hanging around and informing her of what to do next. However, she started to grow close with Craig Field, the head of D&D, which did not sit well with Harry because she started having doubts. He went to Sydney and blackmailed her if she didn't follow through the plan, he would tell the judge that Sydney was conspiring all along.
Later, after Sydney confessed the whole scam to Craig, Craig broke into Harry's office and stole all of Sydney's files. He then physically threatened Harry into agreeing to a small but suitable settlement for Sydney and the case was finished.