The two Teen contestants who have been the most aggressive: Tyler Allard and Leonard Cooper.
In his quarterfinal of the 2003 Teem Tournament, Tyler went for a $10,000 Daily Double bet late in Double Jeopardy, and hit it, cementing a spot in the semis.
Then, on the final clue of Double Jeopardy of Game 2 of the final, Tyler did it again, betting $10,000. Not being completely aware of the situation, though, it was a situtaion where a larger bet would have been better. Tyler ended up $199 short of having a lock tournament. Then, instead of betting just the $200 he needed to in Final, he instead elected to bet 100 times that much – a shocking $20,000, which handed John Zhang the tournament when he missed Final Jeopardy.
2013 Teen Tournament winner Leonard Cooper (as opposed to 2011 Teen Tournament winner Raynell Cooper—how many Jeopardy fans have confused those two players?) made one of the bolder Day 2 moves in tournament history when he bet $18,000 of his $18,200 late on Day 2 of that year’s final. It worked out for him, as he had a massive (but not insurmountable) lead going into final. Leonard thought it was insurmountable, as evidenced by his “Who is some guy in Normandy But I just won $75,000!” response. Fortunately, for him, Nilai Sarda missed Final Jeopardy, otherwise Leonard would have had some significant egg on his face!