We contrast two approaches to optimizing the Common Lisp typecase macro expansion. The first approach is based on heuristics intended to estimate run time performance of certain type checks involving Common Lisp type specifiers. The technique may, depending on code size, exhaustively search the space of permutations of the type checks, intent on finding the optimal order. With the second technique, we represent a typecase form as a type specifier, encapsulating the side-effecting non-Boolean parts so as to appear compatible with the Common Lisp type algebra operators. The encapsulated expressions are specially handled so that the Common Lisp type algebra functions preserve them, and we can unwrap them after a process of Boolean reduction into efficient Common Lisp code, maintaining the appropriate side effects but eliminating unnecessary type checks. Both approaches allow us to identify unreachable code, test for exhaustiveness of the clauses and eliminate type checks which are calculated to be redundant.