First off, you couldn’t have made two bets, one on Hillary Clinton to lose and the other on Donald Trump to win. Sports betting, as it's conducted in casinos, isn't like stock investing (with long and short positions) or craps (with do and don't bets). Your bet on Donald Trump to win was also, per force, a bet on Hillary Clinton to lose.
So let’s just look at bets on Donald Trump. Trump was the underdog throughout the long campaign. If you’d bet $1,000 on him to win the election when he first announced his candidacy, you’d have collected a cool $150,000 (the line at that time was 150-1). Could you have retired on that? Maybe — in Ecuador or the Philippines.
Now, right after the Democratic National Convention with the big bump in the polls for Clinton, Trump was a +650 dog. If you’d bet $1,000 on him then, you’d have won $6,500. That might buy you four months of retirement — in, ironically perhaps, Arkansas (which has the lowest cost of living in the U.S.).
On your $1,000 Trump bet at +275, with a return of $2,750 reported in the LVA November issue, you could maybe go for a couple months (using every coupon you could find) in Las Vegas.
Overseas and offshore sports books reportedly lost big on the Trump victory. The biggest hit was taken by Irish bookmaker Paddy Power, which says it lost $4.5 million (in part because it actually paid out $1 million on Clinton wagers prior to the election as a publicity stunt). Ah, if you'd only been on the winning side of that $4.5 million, you could’ve retired handsomely in your home town.
