The Bet: The Washington Capitals will defeat the Toronto Maple Leafs in the 2017 NHL Playoffs.
Given the absurdity of the bet Tippy has given Jimmy a 2 game cushion.
In other words Washington will have to win by at least 3 games (4-1) for Tip to win.
A 4-2 outcome will mean a push (no one wins).
Anything else and Jimmy gets fatter.
Date: April 13, 2017.
The Bet: The Ottawa Senators will reach the 2nd round of the 2017 NHL Playoffs
Date: April 7, 2017.
Jimmy is going way out on a limb for this one as Ottawa could still face the Washington Capitals in the 1st round (not likely).
Bolstered by Tip's insistence on having this bet and the recent crushing losses Tip has experienced (see bets 22, 24, 25) Jimmy feels both sympathy and confidence in Tip's ineptness.