Their chief of marketing, Claire Harris, who is also Dwight's fiancée, comes up with an idea to announce a contest seeking the biggest loser in the country.

He is running a not overly successful business of renting out boats during summer time and is, by his own description, lazy and completely unmotivated.

Tad comes to New York City to collect his prize, determined to use the money toward a fire engine needed by the small town.

Tad is charmed by Claire during a night out in the city and falls in love with her, all the while expounding his own philosophies on relaxation, enjoying life, and the unimportance of money.

After a while, Tad shyly admits to Claire that he is in love, but he doesn't dare tell her she is the subject of his affection, inventing a girl from his hometown named "Hazel".

The next day, after dodging Claire's many phone calls, Tad uses a special relaxation technique on Frank to help him pass the necessary physical, then proceeds to Dwight's office to vent his anger.