It’s Not So Easy – Gambling With An Edge

I’ve been playing video poker promotions for almost 30 years, and before that exploited blackjack promotions for about five years. I’ve absorbed a lot of “how to do things” over the years that are now second nature to me. When a new promotion comes along, I have enough experience, usually, to get the most out of it.

Recently, though, in another gambling game where they were giving away money, I was really out of my element.

In mid-September, Captain Jack Andrews and Rufus Peabody came on our podcast to promote their new website,  This site contains a lot of information useful to a wide variety of sports bettors. Right now it’s free to download and use. Someday they’ll start charging to use it, but right now they want bettors to come in, poke around, and see if it’s useful to them.

One of the things Captain Jack mentioned was that Arizona had just opened up sports betting, and through the end of September several sports books were giving away free money. “There are no free lunches,” Captain Jack said on the air, “but this is about as close as it gets.”

There were a variety of free bets — two for $5,000 and three for $1,000 — at various books. I didn’t know what a free bet was, but I learned. Doing away with the house vig for a moment, the way a $1,000 free bet works is as follows: Let’s say I’ve chosen the Kansas City Chiefs – Baltimore Ravens bet in week two, where the Chiefs are favored by 3.5 points. To me this was a no-brainer bet. The Chiefs were one of the favorites for the Super Bowl. The Ravens had a lot of injuries and had lost the previous week to the relatively lightly-regarded Las Vegas Raiders. 

If I bet the $1,000 on the Chiefs and they cover, I get $2,000 back. The $1,000 I bet and the $1,000 I win. If Baltimore wins, or loses by 3 points or less, I get a $1,000 free bet in the future. On this free bet, I just keep the winnings and I don’t get the original bet back. 

So, a buddy and I decided to do this in a way that minimized variance. The first week we bet, we’d both take the Chiefs on $7,000 worth of bets. That could be Caesars $5,000, BetMGM $1,000, and FanDuel $1,000. We’d also both take the Ravens for $6,000 worth of bets. In this example, it would be DraftKings for $5,000 and WynnBet for $1,000. If the Chiefs covered, we’d have $14,000 (minus the house vig) which would cover the $13,000 we put up, plus $6,000 of free bets. On the free bets the following week, we could bet the free bets on opposite sides. We’d end up with $6,000 in profit (minus the vig), split two ways.

I’m well-aware that betting these on even-money bets (actually -110 on both sides) is not the optimal way to bet them. If this is of interest to you, there’s an article about it on you should check out. But this was our first time. We wanted to get our feet wet as safely as we could.

Not bad for two drives into Arizona. We both live in Vegas, the border (Boulder Dam) is 30 miles away, and we wouldn’t have to drive too far over the border to find a place with Internet reception. We’d drive over there before noon on Sunday and get our bets down easily before the 5:15 p.m. kickoff time. Piece of cake!

Oh, what we didn’t know!

I thought I could fund the sites by using my credit card. My card could easily handle $13,000 worth of charges, I figured. Well, no it couldn’t. I had never used my card for cash advances, and each card is limited to 10% or 20% of your available credit (depending on the card.) Yes, I could apply for a higher balance, but the decision makers aren’t there on Sundays.

Next choice was online banking. I have some accounts set up, but I’ve never used them. I still take checks to the branch office to deposit them. I wasn’t sure of my online banking login ID or the password. I had my cellphone with me, but not my laptop. Bonnie wasn’t at home so I couldn’t call to ask for her to look some stuff up.

Another problem was that one of the sites couldn’t verify that I was in Arizona. Some setting on my iPhone. My friend took my phone, fiddled with it, and this became fixed somehow. I don’t know what he did.

Still another problem was that one of the sites wanted to verify my address. They wanted me to send a photo of my Driver License (no problem) and a copy of a utility bill, bank statement, or one of a few other things addressed to me within the past 60 days at the address I was using to sign up. All such bills were back at the house, some 50 miles away.

In addition, there was no one address I could use. I use a post office box for all my mail, but in Nevada, they require you to put your home address on your Driver License. Fortunately, I was successfully able to explain this away and my name and address were accepted. My friend didn’t have this problem. He used his home address, and the sports book can find enough references to him there that they didn’t need the proof.

I drove back home, figured out my online banking login info, picked up a bank statement, and headed back to Arizona. I got some of the bets down, but not all of them. And this time, I wasn’t with my friend, who had been able to get most of his bets down. He’d need to put more funds into his online banking account so he’d get the rest of his bets down the following week. I ran into more problems that I wasn’t able to solve before the kickoff. So, we were unbalanced, but still had a significant edge so we should be fine. I passed numerous Nevada casinos with sports book and could have balanced my bets, but it was too late for that. The Sunday night game had already started.

It turned out Baltimore won the game outright. Mostly we were still fine, but we still had to go down and make our free bets. We coordinated who was going to bet on what and went down separately the next week. 

I got one bet down, couldn’t figure out where Caesars kept the free bet, and couldn’t get my Arizona location verified at the third place. So, I came home, waited for my friend to get off work, and together we went down there again.  My two trips had now turned into four! 

Yes, we ended up making money. Several thousand dollars apiece, in fact. But it was an unpleasant struggle. I think of myself as an experienced gambler in a variety of games, but here I was clearly a fish out of water. While this would all have been an easy walk-in-the-park for experienced bettors (but who wouldn’t have been eligible for all of these signup bonuses), for a newcomer there were a significant number of ways things could go wrong.

We’ll probably go to other states to try this. Several states have big enough initial signup bonuses to make it worthwhile to fly to an airport in the middle of another state, make the bets while at the airport, and then fly home or fly to another state that has such deals. We’ll probably run into another bunch of problems, but at the same time we now know more about what to expect. 

And free money is free money.