Have you ever won money?

I’m not a big gambler. Like, at all. In 2015, I went to the NHL Awards in Las Vegas and didn’t gamble a single dime.

While on a bachelor party in Niagara, however, I did go to the casino with the guys and decided to gamble a tiny bit just because I was there. I played a little bit of craps on the first night and wouldn’t you know it, I won $100, and that’s what I left with that night.

It was a great feeling. I walked in expecting nothing, just happy to be there, and walked out with money. The next night we went back. We returned to the craps tables and hey – why don’t I put down some of that money I won? I could double it! And if I lose it – who cares? This isn’t even my money. I’m playing with house money here.

Within two rolls my $100 in winnings were gone.

It was a bizarre feeling. What’s the big deal? I still broke even, didn’t I? I went into the weekend expecting to win nothing and now, here I am, having won nothing.

Except I did win something. I won $100. Then I lost it.

Which brings me to the Maple Leafs.

A lot of people, myself included, have been suggesting the Leafs are simply playing with house money in their series against the Washington Capitals. After all, they’re a rookie-laden team that finished 30th overall a year ago and barely snuck in to the playoffs this year to take on the President’s Trophy-winning Washington Capitals. You might have picked the Leafs to win the series because you’re a great fan, and that’s awesome, but very few people seriously picked the Leafs to beat the Capitals in this series.

Many fans, myself included, decided to view this series as a can’t-lose proposition.

There was a bit of a narrative I often read late in the season when the Leafs’ playoff spot was still in doubt. Many asked, “Hey – at the beginning of the season, did you expect the Leafs to even be here? Can you really be mad if the Leafs don’t make the playoffs?”

Oh, you bet I can.

My thought was that even though I didn’t expect the Leafs to be in a playoff spot at the beginning of the season, they had been sitting in a playoff spot for most of the second half of the season. You could look at them as a young, scrappy team falling just short or you could look at it as they had a playoff spot, lost the playoff spot, and failed to make the playoffs.

So now here we are. The Leafs are up 2-1 in the series. Right now it’s easy to say “Even if they lose this series, they still gave them hell, am I right?”

You’re right, but for the Leafs to lose this series they either have to lose three straight or three out of the next four.

There is definitely more pressure on the Capitals who are clearly in a win-now type of season but the Leafs aren’t simply playing with house money anymore. You play the regular season to make the playoffs and you play the Stanley Cup Playoffs to win the Stanley Cup.

The Leafs’ season so far, regardless of the final outcome, has been a victory any way that you slice it. Now that they have experienced this success however, now that they’re playing with house money, wouldn’t it be better to see them find a way to win big?

If you beat the Capitals… I’m sure I don’t even need to say it.

Big money!