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Operation Toy Drop Continued in NCO’s Honor after His Death

Staff Sgt. Sharilyn Wells
Staff Sgt. Felix R. Fimbres
U.S. Army Civil Affairs and Psychological Operations Command

December 17, 2015

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Members of the U.S. Army Parachute Team, the Black Knights, the U.S. Army Special Operations Command Parachute Team

The first Operation Toy Drop, organized in 1998 by Sgt. 1st Class Randy Oler, collected 550 toys for local children in need. This year, more than 4,300 paratroopers participated and donated more than 6,000 toys. The operation, run by the U.S. Army Civil Affairs and Psychological Operations Command (Airborne,) has become the largest joint airborne operation in the Army.

Contrary to what the name implies, paratroopers do not actually jump with the toys. Soldiers donate new, unwrapped toys for children in need, then are entered into a lottery. Those chosen are awarded the opportunity to earn foreign jump wings from allied jump masters who have traveled to Fort Bragg from around the world.

Operation Toy Drop combines the efforts of Army, Air Force and civilian service organizations in a truly unique event. Since its first year, the operation has expanded to include aircraft support from Pope Air Force Base’s 43rd Airlift Wing and welcomed the participation of Soldiers from Fort Bragg’s XVIII Airborne Corps, 82nd Airborne Division and Special Operations Command.

U.S. Army paratroopers descend on Sicily Drop Zone from a C-130 aircraft during an airborne operation for the 18th Annual Randy Oler Memorial Operation Toy Drop

“It’s a win-win situation,” said Harris Luther, Prime Knight manager for Pope Field at Fort Bragg, North Carolina. “You got the Army guys who don’t get to get foreign jump wings very often, jump with foreign jumpmasters and oh, by the way, help kids by donating a toy. Then the aircrews, when they come in, get (the opportunity) to land in the dirt and fly certain routes, all the while getting guys out the door — which is all training. There’s no losing process here at all, none.”

Who was Sgt. 1st Class Randy Oler?

Oler, a Tennessee native, joined the Army in 1979 as an infantryman. He spent time in Ranger and Special Forces battalions throughout his career, and deployed in support of operations Desert Storm, Provide Comfort and Joint Endeavor. In 1995, he joined U.S. Army Civil Affairs and Psychological Operations Command (Airborne) to become a civil affairs specialist.

“He loved to drink his Mountain Dew and had to have his cigarette with it. You had to get to know him, and when you got to know him — once you learned to know him — you loved him,” said Luther, who met Oler while coaching youth sports. “(He was) just a true American and a very caring person. He truly cared about people. You just can’t say enough good things about him.”

Sgt. 1st Class Randy Oler is the founder Operation Toy Drop, an event in which paratroopers donate a toy to help children around the Fort Bragg community. (U.S. Army illustration by Sgt. Felix Fimbres)

Oler’s close friends describe him as a man’s man, a true American; a gentle giant who loved kids. When he approached four of his close friends with a crazy idea that involved an airborne operation, foreign jumpmasters, toys, children, and lots of fun, they all jumped on board.

The first toy drop in 1998 was small – only a few hundred jumpers exited the aircraft and a matching amount of toys were collected. But Oler had planted the seed, and over the years, his operation grew.

“I thought that the idea, the concept that he (Oler) came up with, was an awesome idea,” said Willie Wellbrook, loadmaster and retired Air Force master sergeant. “Not only for the fact that the jumpers get something out of it but also the big thing was the kids – it’s all about the kids. And I was more than happy to jump on that bandwagon.”

By April of 2004, Oler had been promoted to Sgt. 1st Class and was finishing up an assignment at the U.S. Army John F. Kennedy Special Warfare Center and School. With relocation orders in hand, Oler warned his friends that he might not be there to fulfill his duties for the operation, but he would do as much as he could.

Sgt. 1st Class Randy Oler is the founder Operation Toy Drop, an event in which paratroopers donate a toy to help children around the Fort Bragg community. (U.S. Army illustration by Sgt. Felix Fimbres)

That same month, he suffered a heart attack while performing jumpmaster duties aboard a C-130 aircraft. At 43 years old, Oler was pronounced dead at Womack Army Medical Center at Fort Bragg. After Oler’s death, the operation was dedicated to him in his memory.

“Losing Randy was real hard, because I was here the night Randy passed away on the aircraft,” explained Wellbrook. “I got the call that we had an in-flight emergency. I just didn’t realize at the time who it was – until the next day. Losing Randy was tough, because Randy was the heart and soul of this operation.”

Close friends couldn’t see continuing Operation Toy Drop without Oler; that year’s event was in jeopardy. Oler had been able to do all the coordinating in his head and didn’t write anything down. But by August, Oler’s friends decided he would have wanted them to continue to help children around the community.

“The next couple of years were pretty rough,” said Scott Murray, Oler’s friend and a former Soldier in the XVIII Airborne Corps. “We just didn’t have the heart.”

Wellbrook agreed.

“I don’t think you’ll ever meet another person like Randy,” Wellbrook said. “Randy left a legacy. … It’s blown into a huge operation, and I think Toy Drop will be here as long as kids are in need.”