2. Tiffany Diamond Heist – 727 5th Ave

Diamonds are certainly a thief’s best friend, as this famed jewelry store–which the New York Times called “only slightly more vulnerable than the nation’s gold reserves at Fort Knox–has had more than a dozen robberies through the years. In one incident, according to the Timesa man shot a hole in a glass window and tried to fish out a diamond/ruby necklace with a wire. In September 1994, two armed men dodged the alarms and guards in an “very, very professional job” that was, at the time, the costliest robbery in the company’s 157-year history. They made off with $1.25 million (later calculated to be an even greater $1.9 million) in jewelry (over 300 items) and even covered all tracks by taking the security tapes. While no one was injured, the robbers left four guards bound and made it in and out of the store in a little over an hour. Because they seemed to be so familiar with the security checkpoints and layout, the police suspected the robbery to be an inside job.

A week later, police arrested six men, including two Tiffany employees. Most of the jewelry was recovered, but while the job was “very, very professional,” the aftermath wasn’t. One of the robbers reportedly tried to sell a diamond bracelet worth $6,000 for just $300 on the street, while another tried to sell pieces in Times Square.

Police success in catching these robbers didn’t deter future jewel thieves. Just this year, there have already been two reported thefts at Tiffany’s. In June, a man walked out of Tiffany’s with $100,000 in jewelry. Earlier this month, another, more “professional” job was revealed as former Tiffany Vice President of Development Ingrid Lederhaas-Okun allegedly stole and resold $1.3 million in jewelry throughout her tenure.