Hi Dylan, 'Tipper' - 2 words, one meaning slack (with a letter removed) and one meaning to have dealings ( an old term usually heard as eg I have no ..... with these people) making a rather american sounding tipper.
Optimist - religious anagram of cheats - 1 letter + odd letters of following word.
Meanwhile, can anyone enlighten me on what Boss in Chicago has to do with the apparent answer? Thanks.