OK, so this situation came up tonight, and I THINK we played it correctly (or "interpreted" it right, there really was no playing...)
Villain is Wager Master. The following condition cards were out in the first turn (played in this order.):
The New Deal
Who Are You Fighting? (Not really relevant to the play, but the fact that it was here also means that if we played this right, it was the luckiest setup draw of all time)
Wageling
Losing to the Odds
Heroes are a mix of even and odd HP to start.
Unless I'm mistaken, the resolution of this goes:
New Deal deals 3 damage to any hero with an even starting HP (now all heroes are on odd HP totals)
Wageling deals 1 damage to all heroes (now all heroes are on even HP totals that are less than max)
Heroes now meet the win condition on Losing to the Odds.
And thus did we win the game before the first hero turn. Was this correct, and just the luckiest draw ever? Or did we mess something up?
That sounds about right for Wager Master actually. There was one game where we played with three heros that started with an even HP, two wagelings and Losing to the Odds, and as a result, won the first turn