I’ve sat on this post for several days with concerns about its ramifications if I post it. With a leap of faith, I’ll continue with hopes that everyone that reads it and tries this technique pays attention to my warnings.

I have been buying money orders with my bonus category credit cards for years and scoring big bonuses. I started with an old Delta Amex card when they offered 2 miles for every dollar spent at grocery stores. When the store that allowed me to do it changed their policy, I found another and used my Citiadvantage card for AA miles for 1 mile per dollar.

For the last 4 years I have had a steady stream of Thank You Points coming from my Citi Drivers Edge Options card and AT&T Charter member Universal card with grocery store purchases of money orders. You may try it to, but please: listen to this advice.

1. Don’t be greedy
2. Don’t call attention to your self
3. Don’t call anybody, be it the grocery store, credit card company or even your Aunt Sarah.
4. If you find a Gold Mine, Keep it to Yourself
5. Be Patient
6. Pay Attention

The play is very simple. Walk into a grocery store that sells money orders, pick up just a few things and head to the service counter not the regular register and start the check out process. As the clerk is ringing up your order, ask for a $300 money order and shut up.

One of three things will happen.

a. She/He will ask if you plan on paying with a credit card, say yes and she may tell you we don’t sell money orders with credit cards. You are done. Say: “Ok, just skip the money order”.

b. She/He will get the money order made, process you for checkout and when you hand her the credit card or slide it in the credit card machine, she may tell you they can’t sell money orders with a credit card. Say: “Oh, I’m sorry, skip the money order.” And she will remove it from the order.

c. She/He will process your order and check you out. Take your money order and groceries and leave with a smile. Your $300 money order is worth probably 1500 points in your favorite program as it is a bonus category card you used in the first place paying you 5 points per dollar.

Your next step is to deposit the money order in your bank and use it to payoff your credit card bill when it comes due. Don’t be foolish enough to send the money order directly to your credit card company.

Now come all the questions:

1. Why $300? Because that is the highest amount of the smallest money order offered. Some stores sell money orders that are $500 in size. When you find out, after rinsing and repeating this play, what is the largest denomination Money Order your store sells, you may up your order to a $500 money order. Some stores have a self imposed limit on the size of any order a clerk can take without manger approval. We don’t want a manager involved in our Gold Mine purchase at this point. Go slow, Go easy.

2. Is there a charge for a money order? Yes, usually under $1. Just pay it,. Your points are worth more.

3. Won’t it process as a cash advance? It never has for me and I’ve been doing this for years.

4. Can I do this everyday? Sure, if you want to screw it up for yourself.
Commandment #1 Don’t Be Greedy. I go about once ever week or two and pick up anywhere from $300 to $1000 of money orders to then deposit in my bank account. Here is the math: $1000 per week x 5 points per dollar = 5000 points per week x 18 weeks = 90,000 Thank You Points = a $2700 Business Class ticket.

The reason I lost one of my money order stores this last week was somebody was greedy. They ask for $1700 in money orders and the money order machine spit the transaction back. A supervisor was called in and told the clerk that money orders could not be purchased with credit cards. I had been buying money orders from this store for 4 years and nobody had ever questioned me. It was not a large chain store, and there was no written policy. HINT You’ll have better luck at smaller chain grocery stores.

Now to the other tips: #2, 3 and 4. Don’t call attention to yourself is obvious. If a boss gets involved they may know there is a company policy against paying for money orders with credit cards. It is not illegal, but typically against company policy as the grocery store pays a small service charge for processing the credit card. #3 Don’t call anybody is really the same as #2, but needs to be reemphasized. You are not breaking the law, just staying under the radar. #4 is fairly obvious but if 10 people per day are going into the same store for money orders it will be shut down quickly.

#5 and #6 Be patient and pay attention. Get to know the lay of the land so to speak. I have one clerk in the south that covers the service counter at lunch time. She appears to be a kind of big wig, but not the big cheese and she recognizes me now and all is well. Some clerks work in some stores while other clerks won’t. Which leads to Pay attention. Will it work with every clerk, on every shift or just a few? Pay attention. Weekend help may not know all the company policies.

Ease the amount of your money order purchases up until you hit the limit. If you listen and observe, over time, you’ll hear somebody say what the max money order is or what the maximum purchase is.

Most of the time, you will get shot down the first time in the store, but not always. I walked into a grocery store in Palms Springs CA to buy cigarettes for a friend while we were on a mistake rate at the LaQuinta Resort and Spa. Bam $1000 of money orders topped off our three nights in the Presidential Suite for $25 per night.

And lastly, I’m not the only one doing this. A friend in a larger Midwestern city has hit upon an acceptable variation that is allowing him to amass large numbers of points in his favorite program. He pays a few dollars more than me, per purchase, but he never gets turned down.

The successes change. Stores change policy, you run into a clerk that then tells the entire staff they can’t sell money orders. And you continue to stay under the radar and move on to the next store. Good Luck and let me hear your success stories. Of course, I won’t want to know the store name. That is your secret.

Sometimes you win. Sometimes you lose. Ah, but when you win

I Snagged a Ticket to London

For $251 all in from O’Hare to London and back was too hard to pass up. It will all be elite qualifying miles for me next year on my way to 100K again. I get 6 hours in Heathrow and plenty of time to sleep and write both ways.

Remember the play is multi city and click through once you see the price to see if you won the ticket lottery. ORD-IAD, IAD-LHR, LHR-ORD.

I have no idea how long this one will last, but there is scattered availability through March of 2009.