The What is it? Game

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That was a lucky guess; it was the first thing that sprang to mind when you said about it being a Schneider Trophy aircraft.



The clue is "You gotta know when to hold 'em, know when to fold 'em, know when to walk away, know when to run..."
 
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I am lost on the Kenny Rogers clue

Viking, the RAAF display team is called the Roulettes and the Kenny Rogers song I quoted from was the Gambler - thought that might not have been all that obvious in hindsight!
 

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