The Twilight Zone - Of Late I Think Of Cliffordville

William Feathersmith is a hard-nosed - and hard-hearted - businessman who is now quite wealthy but bored. It's clear that what he enjoys is the chase and the acquisition of wealth. He also likes breaking men in the process. While leaving the office one day, he finds himself on the wrong floor and in the office of Devlin Travel, run by the devilishly attractive Ms. Devlin. In return for his amassed fortune, she offers to send him back in time to his hometown of Cliffordville in 1910 where he can start over and get the pleasure of building his empire all over again. He accepts and once back to the days of his youth begins wheeling and dealing. Nothing quite goes as planned however.