Evan Schuman's StorefrontBacktalk

One of the very best times for a retail thief to strike is when technology is brand-new, because employees don’t yet know what to expect and therefore can’t recognize unusual activity. That’s the hole an 18-year-old Macy’s associate tried to use when his New York store had just started the chain’s new Search-and-Send program, which allows one store to access the inventory from another store and have items shipped directly to the customer.

Indeed, the associate might have gotten away with it, had he not gotten too greedy and obvious. How obvious? He purchased the chain’s most expensive Movado watch—a $2,995 Swiss timepiece with a tungsten carbide bracelet—but not before he “processed an unauthorized markdown” to make the price $2.95. Think a better-than 99.9 percent discount would trigger a flag? The good news for Macy’s loss prevention: It did indeed trigger a flag. The bad news: Nothing in the system stopped the associate, who had worked for Macy’s less than five months at the time, from processing it and having the product shipped.

Based on a review of court and police records, the fraud’s particulars provide a rare look into the mechanics of early-adopter-fraud. (Given the age of the associate, the New York court is considering entering him into a youthful offender program, which would seal all of the criminal records. Because there is little benefit to our readership to have this incident crop up every time someone Googles this guy’s name, StorefrontBacktalk is withholding it.)

The incident began at 6:20 PM on January 26, 2011, in the Dewitt, N.Y., Macy’s in the Shoppingtown Mall. The associate manually marked down the watch, paid for it with his personal Visa card and then used Macy’s Search-and-Send (a.k.a. an E-Send) to have UPS ship it to his home, using his real last name and a different first name.

As a nice touch, he included something to make it look like a gift. According to a statement the associate made to Macy’s loss prevention, “I signed for my purchase on the electronic pad and completed my purchase with a giftcard message stating ‘Sorry for your loss.'” (Note: In Dewitt, N.Y., is it traditional to accompany sympathy cards with a $3,000 watch? On the other hand, maybe the word was intended to taunt loss prevention. Then again, most LP people are not inclined to appreciate clever wordplay from a suspect.)