@DBActive
No professional bookmaker would ever take a bet of $10 and give odds of several hundred $1000s to 1. The downside is too great for no upside.
Actually, the downside for the bookmaker is if everyone bets for the winner.
Outside of sports betting and point spreads, that's what odds are for, to attract enough people to bet on the expected loser.
You aren't really betting against the bookmaker, but against the other bettors. The bookmaker makes his money by skimming a little off the top. He manipulates the odds he offers so that no matter who wins, more money was lost by the bettors in aggregate than was won.
If enough people were betting the other way, a bookmaker might give you those kinds of long odds. In the event that your bet did pay out, there would be more than enough people who lost money betting on the other teams to off set the cost of the payout to you.
The problem is to get those kinds of odds, you need a seriously unexpected upset and you just aren't going to get that every season.
In a do-over situation with 40 years of future knowledge, there isn't likely to be more than 1 or 2 upsets (even across all sports) that could get you odds that long.
ETA: Remember, the house always wins. If the bookmaker sets the odds (or point spread) correctly, the bookmaker comes out ahead no matter who wins the game.
There are two catastrophic situations for a bookmaker. Everyone bets on one side and that side wins. The bookmaker sets the odds/point spread wrong and too many people bet on the long odds and the upset happens.
One person betting long odds is not going to hurt the bookmaker's bottom line unless the initial bet is large.