First off, I'm not a gambling man. My father was gambling addicted when I was a kid, so I've made it a point not to gamble regularly. I don't gamble every week, every month, or even every year, but it's still fun, as a fan sometimes, to believe in your team and put your money where your mouth is.
First of my two "wackiest" Giants bets came in 1980 when I lived in Norwalk, CT. I bet my next door neighbor $10 the Giants would have a better record than the Jets for the decade of the 1980s. At the time the record was still 1-0 Jets when it came to super bowls and the Giants were coming off the worst decade in franchise history, so the bet, to my neighbor at least, seemed like a reach. But by 1980 the Giants had Simms, Young and Perkins. I figured they were on the right track. Won that bet but lived in CA by the end of the decade, lost track of my neighbor and never collected.
Second bet was on the 2008 super bowl. Bet a big Pats fan $1 Giants would win outright. Got 5-1 odds and the victory.
I bet them that, Eli would win another Super Bowl and the Yankees would win another World Series before Brady and the Patriots would win another championship. Even money.
Of course things got interesting after the Yankees won in 2009. Prior to Super Bowl XLVI, I called to remind them of the bet we had made years earlier and they, to their credit, acknowledged that the bet was on.
Arrogance humbled! I was paid $500.
When they end up beating the Packers, my $1200 payout from the Flamingo Hilton turns out to be $240.
Half way through the 2007 & 2011 seasons, you'd have had a very hard time convincing anyone that the Giants would get it together and win the Superbowl again.
Never say never unless you're an Eagles fan.