Middling: The Advanced Strategy That Made My November

Most bettors think you have to pick a side. You're either on the favorite or the underdog. But there's a strategy where you can win both sides of a bet—or at minimum, guarantee a small loss while giving yourself a shot at a big win.

It's called middling, and it made my November extremely profitable.

Here's how it works:

On Monday, the Patriots open as 7-point favorites against the Jets. I think the Patriots will win comfortably, so I bet them -7.

By Friday, the line has moved to Patriots -10. Maybe an injury report came out, maybe sharp money hit the Jets' side. Either way, the line is now three points higher than when I bet.

I now have a decision: I can bet on Jets +10.

If I do, here's my possible outcomes: - Patriots win by 1-6: I lose my Patriots -7 bet, win my Jets +10 bet - Patriots win by 11+: I win my Patriots -7 bet, lose my Jets +10 bet - Patriots win by exactly 7, 8, 9, or 10: I win BOTH bets

That middle zone—7, 8, 9, 10—is worth swinging at. If it hits, I profit on both sides. If it doesn't, I only lose the vig (the difference between the two bets).

My November middle that hit:

Eagles opened -3 against the Cowboys. I bet Eagles -3.

By Sunday, the line was Eagles -6.5. Cowboys starting left tackle and top receiver were both ruled out.

I bet Cowboys +6.5.

Final score: Eagles 27, Cowboys 21. Eagles won by 6. Right in the middle. Both bets cashed.

The keys to successful middling:

You need significant line movement. A line moving from -3 to -3.5 isn't enough—there's no realistic middle. You want at least 2.5-3 points of movement, preferably crossing key numbers.

You need your original bet to be good on its own. Don't force a middle by making a bad initial bet. The middle is a bonus opportunity, not the primary strategy.

Track the cost. If both bets are at -110 and the middle doesn't hit, you're losing about 5% of your total stake. Make sure the middle zone is likely enough to justify that cost.

Middling isn't an everyday strategy. You need the right circumstances. But when they appear, it's one of the few ways to win both sides of a sporting event. And there's nothing quite like watching a game knowing any score in a wide range is a win for you.