On the morning of September 11, 2001, John Perillo looked out of his office window at 1 Whitehall Street in Manhattan and saw a plane flying at a dangerously low altitude. Almost instantly, his building began to shake. Seven blocks away, the plane had struck the World Trade Center.

It would be hours before Perillo and other New Yorkers were able to grasp the gravity of the situation. A terrorist attack on American soil stunned the world and created a widening panic and confusion before a kind of resolve set in. For Perillo, the vice president of operations at Topps Trading Card Company, and Topps CEO Arthur Shorin, it would become a time to memorialize the events of that day in the medium they understood best. Which is how Osama bin Laden came to have his own trading card.

Bill Pugliano, Getty Images

Although they were best known for sports cards, Garbage Pail Kids, and other entertainment properties, Topps had already recorded a significant history with real-world events. In 1950, they found success with a line of Korean War cards. More than a decade later, they memorialized the Civil War. A set reflecting on the life of John F. Kennedy following his assassination was released in 1964. In 1991, a line of cards depicting Operation: Desert Storm received endorsements from Colin Powell and General Norman Schwarzkopf.

Within a week of the attack on the World Trade Center, Topps executives decided to pursue another—and substantially more controversial—line based on current events. Titled Enduring Freedom, the line featured 70 cards of figures like President George W. Bush, National Security Advisor Condoleezza Rice, New York City Mayor Rudy Giuliani, New York Governor George Pataki, and bin Laden. There would be cards of military vehicles and weapons; on the back were biographies of political figures and descriptions of the hardware. The goal, Shorin told the press, was to give kids information about the rising conflict in a format with which they were already familiar.

"Kids need to get information on their own terms," he said. "This is their medium."

While the plan came together quickly, the company largely avoided depictions that might upset children or their parents. One card featured a smoke-filled view of the transformed Manhattan skyline, but no pictures of the destruction or rubble were considered. In a departure from conventional card sets, no "chase" cards—or rare inserts that prompt consumers to buy more packs—would be involved. There was some internal debate about including bin Laden, but the company ultimately decided that kids might want the opportunity to defile his image by ripping it up. It's the only black and white card to appear in the set.

"We wouldn't be surprised if they tear, stomp all over it, and dump it in the garbage," Shorin said.

Bill Pugliano, Getty Images

Enduring Freedom was released in October 2001, which marked a rapid turnaround time for the card industry. (Sets typically take months to come together.) Hobby shops and larger retail outlets like Walmart accepted shipments of the 7-card product, which sold for $2 per pack, but not everyone was comfortable monetizing the tragedy. Stores in Chicago refused to carry the line, citing concern over appearing insensitive. (An unrelated 2002 card set by Chestnut Publications eulogizing victims of the 9/11 attacks, which was created with their families' permission, drew related headlines and accompanying criticism.)

In interviews, Shorin argued that the cards and their explanation of America's military would be comforting to children: Topps had consulted with child psychologists to make sure the content was age-appropriate. Though they were reticent to publicize it, the company was also donating a portion of proceeds to relief efforts. They even shipped 1 million cards to troops stationed overseas.

Ultimately, the notion of potentially trivializing the War on Terror never caught on. Topps never released a planned second wave that would feature high-tech military hardware, a likely result of the cards selling only modestly. As one store owner pointed out, it wasn't that the cards were offensive—it's just that kids were too preoccupied with Pokemon to bother.