This Day in History: Raymond Wilkins's Bravery in the Sky

On this day in 1944, a hero receives a Medal of Honor. Raymond “Wilkie” Wilkins once aced the written entry exam for West Point, but then he failed the physical requirements for that academy because his teeth were slightly crooked!

Undeterred, he enlisted and began his Army career as a private. From there, he was soon learning to fly at the Air Corps Technical School.

“He wanted to be Army; Army with a capital A,” a Portsmouth Star reporter wrote in 1945. “That is the core of the story of the flier who was known throughout the Southwest Pacific as ‘Wilkie’ Wilkins.”

As a B-25 pilot, Wilkins proved himself early and often during World War II. By October 1943, he was a squadron commander with dozens of combat missions and more than 250 combat flying hours under his belt. He’d earned a Silver Star, four Distinguished Flying Crosses, and two Air Medals.

He had a reputation for being gutsy and was thus assigned many of the tougher missions.

His Medal mission would be one of these. American forces were then trying to take out the Japanese at Rabaul, on New Britain Island. Bombings had been ongoing for weeks, but the Japanese unfortunately received more reinforcements during the final week of October.

Nine squadrons of B-25s, including Wilkins’s, were dispatched for an attack on November 2.

His bomber was hit almost immediately that day, but perhaps that was unsurprising: His plan of attack had put his own aircraft in the riskiest position. The hit left his right wing damaged and his control of the B-25 compromised.

No one would have blamed him if he’d tried to limp back to base. Naturally, he wasn’t going to do any such thing. He had bombs aboard, and he intended to find his targets.

“He strafed a group of small harbor vessels,” his Medal citation describes, “and then, at low level, attacked an enemy destroyer. His 1,000 pound bomb struck squarely amidships, causing the vessel to explode.”

Antiaircraft fire from this last ship hit Wilkins’s bomber, this time damaging his left vertical stabilizer. Naturally, the plucky pilot was undeterred and simply kept going, attacking and destroying an enemy transport with his last bomb.

Finally, Wilkins signaled his squadron to withdraw, yet he could see that a cruiser was directly in his men’s path.

“Unhesitatingly,” his Medal citation notes, “to neutralize the cruiser’s guns and attract its fire, he went in for a strafing run. His damaged stabilizer was completely shot off. To avoid swerving into his wing planes he had to turn so as to expose the belly and full wing surfaces of his plane to the enemy fire; it caught and crumpled his left wing.”

At this point, Wilkins lost all control over his plane. He crashed into the sea, yet his sacrifice meant that every other remaining plane in his squadron made it safely home.

Reportedly, his men were seen openly weeping when they learned that their commander hadn’t survived his plunge into the ocean. “He was only twenty-six,” Captain R.W. Baldwin said. “A good many years younger than me. But he seemed older in a lot of ways. He seemed almost like a father—even to me.”

Wilkins was posthumously awarded the Medal of Honor about a year later.

“His ability as a combat pilot set the criterion that all of us strive to attain, but none ever equal,” his successor as squadron commander said, “and his personal character was an example for every officer . . . . No other man that I have ever known came so close to achieving the standard set by ancient chivalry—that of being ‘without fear and without reproach.’”

Yet another member of the Greatest Generation, giving all that he had to give.

Rest in peace, Sir.

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Primary Sources:

• Bill Yenne, MacArthur’s Air Force: American Airpower over the Pacific and the Far East, 1941–51 (2019)

• Biography and People: Wilkins, Raymond Harrell (NCPedia)

• John L. Frisbee, Raid on Rabaul (Air Force Mag., Nov. 1987) (p. 112) (available HERE)

• Margaret Russell, Many Carolina Alumni Given Awards for Bravery in War (Herald-Sun; Apr. 24, 1944) (p. 8)

• Medal of Honor citation (Raymond Harrell Wilkins; WWII)

• Medal of Honor Posthumously Awarded to Portsmouth Pilot (Virginian-Pilot; Apr. 7, 1944) (p. 3)

• Sid Moody, An Affirmation of Survival: Class of ’38—a portrait of America (Houston Chronicle; June 11, 1978) (p. 4, Sec. 2)

• Top Medal is Given 83 Since Pearl Harbor (The Times; Apr. 19, 1944) (p. 3)

• Wilkens—Maj Raymond Harrel Wilkens (Air Force Historical Support Division)

• Will Oursler, Heroic Life of Late Major Raymond Wilkins Told in National Magazine Article (Portsmouth Star; July 8, 1945) (p. A-3)