1994 - our first two-timer
In our 5th contest, we had our first two-timer. 1992 winner Norm Rosen won for the second time in three years, giving him 40% of the contest titles (2 out of 5). His performance was even more dominant considering he didn't play the contest in 1990 or 1991. A dynasty was looming. We were facing the Yankees of the Pre-NCAA pool.
But Rosen never won our contest again.
However his feat did stand the test of time. The contest was 23 years old before our next two-time winner. Actually, two years before that (in 2010) we handed out the winning prize to a previous winner, but Biebel, who had won the contest in 2004, really finished second in 2010, only taking the first prize money because the true winner, Crotty, was a non-paying contestant. It wasn't until 2012 that we had a two-timer (other than Rosen) who truly finished first twice, that double-dipper being Harlan, who had previously won in 1993 (coincidentally, the year in between Rosen's conquests).
Somehow the floodgates had opened, because after going 20+ years in which Rosen was our only two-time winner, our 2016 champion M Peloso (who had previously won in 2007) became the 4th such individual (counting Biebel) in seven years.
The third of those four was 2014 winner Baumgarten, though similar to Biebel, Baumgarten's 2015 first prize winnings were courtesy of an actual winner (Tester) who didn't have the sense to pay for his entry. In 2017, Baumgarten became a true two-timer, and our only three-timer, winning the first prize money for the third time in four years.
As a fitting monument to his brilliance, on his historic 2017 entry form Baumgarten misspelled his own name.