You'd think that once Michael Westen had managed to get out from under the guys who burned him, life would get easier. Then this Miami detective showed up to give him a hard time. But that's not the worst of it.

Michael's gal pal Fiona (Gabrielle Anwar) is an enterprising young woman: she always seems to have quite a bit of money, and the connections to pull off some lucrative jobs.  For several episodes now, she's been trying to convince Michael that he could give up on his ungrateful spy life and settle down to make some real bucks in the private sector.

As the episode starts off, she's got one of these little gigs set up, a simple "gimme" collecting money from a guy named Randall, introduced as a "charming sleazebag." If they're successful at retrieving the stolen $20K, they'll get five of it. Michael starts getting excited about using his share to help get his spy life up and running again-- Fi says "I'd rather you spent it on drugs."

The job goes bad, however, when the determined Detective Paxson (Moon Bloodgood) shows at the scene, and worse, leaves Michael a police "babysitter." This chaperone follows Michael for several days, until he finds a clever way to get rid of him:  Michael tracks down Paxson at a stakeout, cop in tow, and she's forced to send the cop away to avoid blowing her own eight-month investigation.

Michael assures her they're on the same side. She challenges him to prove it.
This opens the door for Michael to help catch the big-time criminal Paxson's been hunting, a guy named Matheson (Erik Palladino) (the character's name a tribute to several-time series director and guest star Tim Matheson).

To gain entry to Matheson's clique, Michael sets his sights on dissatisfied "middle manager" Tommy (NYPD Blue's Nick Turturro).  He buddies up to him, at the dog track, echoing Tommy's own accent and attire, and convinces Tommy his little crew is hungry and wants Tommy to lead them to greatness.

Of course, the reason Tommy is in middle management is because he's NOT that great, and our team ends up having to walk him through HIS planned ripoff of a drycleaner, making him feel all along like the ideas are his very own. This effort produces some very funny moments.

Other funny sequences include the IRS audit of Sam Axe(Bruce Campbell) by a humorless young man named Stacey (A Boy Named Sue, anyone?) who turns out to be a shadowy figure from Sam's past, and the brief appearance of Sharon Gless as Michael's mother Madeline, who sighs, "I'd appreciate it if the only time you stopped by wasn't to lose your police tail."

In the end, Michael meets the detective's challenge, and she calls off her dogs--for now. Michael realizes he's free again, and as he and Fiona have dinner to celebrate, they blurt out that this is the moment each has been waiting for. But oh so clearly, it's for different reasons. The battle for Michael's soul between Fiona's style of freedom and his old life is square on the line--and her tears are the clue which side is winning.