I normally don't bump threads this old, but I was doing some Sale research for a personal project of mine earlier and learned that the lady in the upper right is likely named Maureen McGovern. According to several recollections, she left with the cash jackpot ($54,000) on 5/27/83 and was supposedly the first person to do so. The commercial below aired the 29th, so the clip featured likely aired the following day.
I'll try to find something a bit more conclusive on newspapers.com regarding that.
5/29/83 was a Sunday, so I think the clip featured was the introduction of the cash jackpot unless NBC spoiled the outcome of the following day's episode. I think we can pin down the beginning of the cash jackpot era as 5/23/83, and the order of the first four cash jackpot winners were:
Maureen McGovern 5/27/83
Richard Heft 7/13/83
Barbara Phillips 8/9/83
Fran Wolfe 9/1/83? (Assuming she won a $66,000 cash jackpot)
And back to the photo of the nine contestants, I don't think that's Ray Winston, and I don't think he participated in the 1983 tournament of champions. I'll explain.
In the lawsuit that Mr. Winston filed against NBC for nonpayment, the dates Mr. Winston taped his episodes were November 11 & 13th, 1983. NBC was airing the tournament of champions at the time and started airing those episodes in October.
The history of $ale of the Century is one of the more intriguing aspects of game show fandom because we are trying to piece it together with the little bits of info that comes out every few years.