It's Always Sunny In Philadelphia: 10 Best Characters Who Appeared After Season One
6. The Lawyer
Another example of someone whose interaction with the gang ended up ruining his life.
The Lawyer (we never know his name) has been an antagonist of sorts to the gang since he appeared in season three. Often aggravated by their presence and ridiculous problems, the Lawyer eventually develops a deep hatred for the gang and routinely gets one up on them.
In season five, he actively represented a family against Frank Reynolds and the gang and also threatened to kill Charlie who foolishly challenged him to a duel. Later on, with Charlie's business Kitten Mittens taking off, the Lawyer rigs a contract that the gang signed which hands him all royalties and leaves them with nothing. (Apart from Mac, who had a mouthful of paper.)
When Dennis got divorced from Maureen (more on her later), the Lawyer represented her pro-bono due to his hatred for Dennis. Smart and witty, the Lawyer always won the battles and the war with the gang until episode eleven. In a court room based episode, the Lawyer is attacked by Royal McPoyle, a vicious bird that attacks his eye. In the chaos of the courtroom, the Judge throws out the case, leaving the Lawyer blinded and defeated by Charlie in the end.