I won a trip to the Bahama's in the early 80's (through work)!...2K
Worst prize was 1,000 dollars. Best prize was a 10 day trip to Paris, all paid for.
I walked out with a 7 day stay all inclusive trip to aruba + airfaire (8K ish value) had to pay the taxes on it. 500 bucks if I remember correctly.
Buddy walked out with 10K-ish of golf stuff and I thought his wife was going to fucking kill him(pure luck)