Bug / Dragon
Not only have I been waiting for a Bug / Dragon Pokemon since RBY, but its fantastic offensive STABs and poor defensive typing (with four common weaknesses to Flying, Ice, Dragon and Rock) will, I feel, fulfil this CAP's main objective of Risky Business very well. Bug / Psychic's mediocre STAB combination and multitude of common weaknesses (Fire, Rock, Flying, Dark, and Bug... and an uncommon Ghost weakness to boot) mean that it would be very difficult for it to be rewarding to use effectively.