Who was Randy Oler?

Story by Staff Sgt. Sharilyn Wells
and Staff Sgt. Felix R. Fimbres
November 2010

Randy Oler is name that has been coupled with Operation Toy drop for years, but not many know why. Like Iron Mike, you may think he was part myth, part legend. For those that knew him he was both and yet more. To his friends he was a Giant, a Saint, but more importantly a Friend. His herculean efforts forged a Fort Bragg tradition, a tradition of giving, friendship, and camaraderie.

Oler, a Tennessee native, joined the Army in 1979 as an infantryman, spending time in Ranger and Special Forces battalions throughout his career, and had deployed in support of Operations Desert Storm, Provide Comfort and Joint Endeavor.  In 1995, he joined USACAPOC(A) 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 Harris Luther, Prime Knight manager for Pope Air Force Base and who met Oler while coaching youth sports.  “(He was) just a true American and very caring person. He truly cared about people. You just can’t say enough good things about him.”

His close friends describe him as a man’s man, a true American; a gentle giant who’s only weakness was children.  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.

“When Randy asked you to do something you’d be honored because, one, you weren’t sure if it was legal, two, you’re not sure if you were going to get away with it, and three, it was going to be fun,” joked Caldwell, who was then a staff sergeant for USACAPOC(A) at the time. “So we figured, okay, the air operation is legal and we figured with enough buds around here we could get it done, and it sounded fun. It was, but we didn’t think we’d ever see another one.”

Operation Toy Drop was born in December of 1998. The first toy drop was small, only a few hundred jumpers exited the aircraft and a matching amount of toys had had been collected.  But Randy 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.” Over the years thousands of paratroopers from Fort Bragg have joined the bandwagon. So far Operation Toy drop has collected more than 35,000 toy donations. Last year, the event drew more than 2,000 paratroopers, 2,900 toys, and 24 allied jumpmasters.

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 may not be there to fulfill his duties for the operation, but he was still able to prepare as long as he could.

On April 20th, 2004, Sgt. 1st Class Randall R. Oler 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. 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 past 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 on Operation Toy Drop without Oler; that year’s event was in jeopardy. Oler was able to do all the coordinating in his head and didn’t write anything down. But by August, Oler’s friends looked at each other and decided that Oler would have wanted them to continue on to help children around the community.

“He would have been kicking us in the butt if we had decided not to do it because he wasn’t here. We would have wasted all the years he put into it,” said Caldwell. “So, we revitalized ourselves and got started.”

“The next couple of years were pretty rough, not because of the loss of Randy, but because it was like a horse leading us to the barn. We knew where we wanted to go, but we just didn’t have the heart,” agreed Scott Murray, friend and former Soldier in the XVIII Airborne Corps. “This year, something happened with us originals; we’re called the originals, the old timers, or the fuddy duddy’s — whatever you want to call us. But we’ve been here since the beginning and I think Randy would love it because he would be right here with us.”

“We have said that if Randy could see us now, he’d be laughing that (the operation) has gone from ‘hey bubby, can you help me get 200 people on a jump to maybe having 2,000 people jumping for the first day alone and possibly having 4,000 to 5,000 toy donations,” laughed Caldwell.

Randy’s Toy Drop has become the largest joint airborne operation in the Army, spearheaded by the Army Reserve’s USACAPOC(A) with the help of Pope AFB’s 43rd and 440th Airlift Wings, and the participation of Soldiers from Fort Bragg's XVIII Airborne Corps, 82nd Airborne Division and Special Operations Command. Since its inception, Operation Toy drop has collected more than 35,000 toy donations.

“I don’t think you’ll ever meet another person like Randy,” Wellbrook reflected. “Randy left a legacy and I think his legacy is what he said on the back of that pickup truck with (friend), Scott Murray. It’s was what he could do for local kids and he hit the ground running. It’s blown into a huge operation and I think Toy Drop will be here as long as kids are in need.”

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