Jerry takes to murder like a pro. Sure, he vomits a little the first time, but a few more rounds of watching guys get whacked, and he’s ready to jump in, guns ablaze. Quite literally, in some cases. And this gets Jerry into trouble.

Jerry never quite cottons onto the rules, or to the code. He wants to make an impression, he wants to shake things up. So he tries something different. Needles instead of guns. Public executions (amid a crowd of tourists in Florida, of all places). You might say Jerry’s a bit of an artist when it comes to making hits… Or you might say he’s a bit of a berserker*.And that doesn’t work so well.

What’s to be done, though? How can Jerry be a good little contract killer, carry out his job like every other guy, and still be the slightly nutty guy he is? He’s got to obey the rules—there are reasons for the rules—but like can’t always be by the rules, and life can’t always reform.

Does part of the answer stand in life outside of the job? Maybe. I would venture to argue that, yes, it does. And Jerry doesn’t quite know how to separate the two. Life and the job become a murky mixture, and he’s stuck in that gray area that nearly leads him down a very bad (call it, at the very least, rather unsettling) path. Furthermore? I’d argue that this very problem runs through each play in Working It Out. Characters who can’t hold a life outside of work become lost, can’t find those other ways of expressing themselves (and so lose the once so nearly held talent to, say, create stories or work up a comedy act).

So Jerry’s life is maybe not quite in order.

Added to which is the fact that, historically, the mob has spent the last twenty plus years moving to behind-the-scenes work. As their stranglehold on the Windy City (and elsewhere, but we’ll stick with the Jerry and Tom setting for now) was shaken, members of the Mafia learned to keep murders and other, ah, uncouth activities very hush-hush; if they couldn’t pull strings or talk their way out, they needed to learn how not to be caught. Busting in and shooting up a joint was out; a quiet execution and a body dumped by the roadside or thrown into a mixture of concrete were in.

And think about it. One man with mob connections takes to public execution, he gives the entire mob a bad name. Gives a target, and gives cops an angle for investigation. So the kind of tricks Jerry pulls? Very bad for the Mafia. And, thus, very bad for Jerry.

-Kristi