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Amid the gathering gloom descending on London in 1939 there remained pockets of glitz and glamour. Few members of that privileged world moved in more sophisticated circles than Charles and Bobby Sweeny, the handsome, Oxford-educated sons of an American financier. They knew everyone who was anyone in London, consorting with royalty and nobility, political and military elite, actors and sports heroes. Their friends ranged from Ambassador Joseph P. Kennedy’s brood to movie stars David Niven and Merle Oberon. It was as if the Sweenys had stepped out of an F. Scott Fitzgerald story.

Long before America entered World War II, the Sweeny brothers used their connections to join the British war effort. Charles, the elder at 30, organized the RAF Eagle Squadron, a legion of American volunteers that would eventually number 244 pilots,with the help of his uncle, Colonel Charles Sweeny. The squadron became a natural home for rambunctious Yanks desperate to fly the hottest machine around, the Supermarine Spitfire. Between the Eagles’ first combat action in July 1941 and September 1942, when the three Eagle squadrons were transferred to the U.S. Army Air Forces’ 4th Fighter Group, the American pilots destroyed at least 73 enemy aircraft.

Younger brother Bobby, who had won the British Amateur golf championship in 1937, was in the States when Britain entered the war, but returned to England and tried to join the RAF. Told he was too old to be a fighter pilot, he first opted to serve as an adjutant in the Eagle Squadron. “Bobby, however, was not the kind of man to play anything but an active role in anything,” his brother noted. “His decision was strengthened by the attitude of some of the pilots, who made it clear that they saw him as a rich and pampered playboy. Bobby was determined to show them—and he did.

“He pointed out to everyone who would listen that the RAF was in no position to refuse the services of an officer who had 50 hours of flying time,” Charles continued. “I have heard him accused of taking advantage of his friendship with influential people to get into the RAF. I can assure you, he used his charm and every other wile short of blackmail on every influential person he could find—and it worked!”

Bobby Sweeny succeeded in getting his wings, but since he could not be considered for Fighter Command, he was posted to Coastal Command’s No. 247 Squadron under Air Marshal John Slessor, flying Consolidated Liberators. Even while preparing for combat, Bobby maintained his posh lifestyle. Rather than living at the pilots’ encampment in Torquay, he stayed in the Imperial Hotel, driving around the countryside in his Bentley and dining regularly with Brig. Gen. Alfred Critchley, an old golfing companion who had been assigned to serve as air commodore in charge of training pilots.

Bobby would eventually fly more than 800 combat missions. Early on, while patrolling off Norway’s coast, he spotted the pocket battleship Lützow. Sweeny’s squadron leader wouldn’t risk a bombing raid at that point, but the Liberators shadowed the cruiser, forcing it to retreat to the Norwegian fjord where it spent most of the war.

Over the Bay of Biscay on May 31, 1943, Sweeny encountered the German submarine U-621 while its crew was searching for survivors from a sub that had gone down nearby. He dropped 12 depth charges on the U-boat in two runs, severely damaging it.As they watched the stick of bombs impact right across the sub’s nose, Sweeny and his crew were certain they had destroyed the vessel. U-621 submerged, and Sweeny reported seeing a mass of oil and debris, including dozens of oranges, come bubbling to the surface. To everyone’s surprise, however, after returning to base they were awarded a probable kill. As it turned out,the severely damaged U-boat managed to limp back to Brest, France, on June 3.

While patrolling that same area on July 28, Sweeny recorded a confirmed kill—though he almost didn’t live to celebrate it. It began when a Liberator piloted by Major Stephen McElroy of the USAAF’s 4th Antisubmarine Squadron located U-404 northwest of Cape Ortegal, on Spain’s northwest tip. A veteran of six cruises, during which it sank 13 merchant ships and a destroyer, U-404 had left St. Nazaire on July 24 bound for the North Atlantic.

On his first attack, McElroy’s depth charges failed to release. When the U-boat resurfaced, he dropped eight depth charges onto its diving point, but then flak damage to the B-24’s radio and an engine forced him to turn back. After the sub surfaced again, another Liberator from the same squadron, flown by 1st Lt. Arthur J. Hammar, target edit. But he too was forced to break off his attack due to flak damage.

Then Sweeny, flying with RAF No. 224Squadron, headed for U-404. At 1,000 yards his gunners began firing, and the sub’s crew responded. Sweeny ignored the barrage to drop his bombs on target and finish off the U-boat, even as a shell smashed into his right wing, damaging its outer engine. As he pulled up, the bomber was shaking. He was forced to run the three undamaged engines at full power, but whenever he tried to gain altitude, the Liberator threatened to stall.

Sweeny ordered everything not nailed down tossed out of the bomber. He gradually managed to gain altitude, but he knew the Liberator was an easy target. His options were limited: He could divert to Spain,where the crew and plane would be interned; he could contact the British light cruiser Glasgow patrolling nearby, and hope its crew would fish him and his men out of the water if they went down; or he could try to limp back to RAF St. Eval, 400 miles distant. But with the remaining engines running at maximum power, they were unlikely to have enough fuel to cover the distance. And they would have to fly along the French coast, well within range of German fighters.

Deciding to head for St. Eval, Sweeny ducked into the clouds for cover, though he had to fight to maintain altitude. Charles later wrote of his brother’s ordeal, “Every time they started to lose height, they found something else to throw overboard, until even the life-rafts were gone.”

Over the Brest Peninsula they broke out of the clouds and Sweeny spotted a Ju-88C just 50 yards away—close enough that he could discern the surprised look on the German pilot’s face. The American maneuvered back into the clouds before the Junkers could pull up and open fire. Sweeny realized he couldn’t risk flying in the open; he would have to cloud-hop toward base,using up precious fuel.

As his crippled Liberator neared St.Eval, the clouds that had sheltered Sweeny became his adversary: He was having trouble finding his way home. The base dispatched a pair of Spitfires to lead him in, but to no avail. The Liberator finally landed at St. Mawgan, three miles from St.Eval, as it had a longer runway. Bobby’s commanding officer, Arthur Clouston,who had been monitoring the situation from 800 miles offshore, told Charles, “I thought he would never make it.” Two months later the Associated Press reported that the “golfer who won the 1937 British Amateur Championship…prodded his crippled plane on the 400-mile trip home on three engines, seldom flying more than a few hundred feet over the water. His ship was defenseless against enemy fighters as everything movable, including guns, had been thrown overboard to lighten the load.” Clouston recommended Bobby for a Distinguished Service Order, but the station commander rejected it. Instead he was awarded the Distinguished Flying Cross, which King George VI presented to him at Buckingham Palace.

After the war, Bobby Sweeny went to work at his father’s London firm and resumed his golf career. He again reached the finals of the British Amateur in 1946, but lost. He also courted Woolworth heiress Barbara Hutton—losing her to Cary Grant. In 1949, at age 37, he married 18-year-old New Yorker Joanne Connelly. Their marriage would end in a messy public divorce after the birth of two daughters. Bobby’s next big disappointment came in 1954, when he lost on the final hole of the U.S. Amateur to the then-unknown 24-year-old Arnold Palmer, who called Sweeny “the finest striker of the ball I’d ever seen.”

The Sweenys maintained their friendship with the Kennedy clan over the years of wintering in Palm Beach. In 1963, when a vacationing President Kennedy was riding in a motorcade, he spotted the Sweeny brothers playing the 16th hole at the Everglades Club. Ordering his car to stop, JFK jumped out—followed by two Secret Service men—and walked out onto the course to greet his old friends.

Bobby Sweeny died of cancer in October 1983 at age 72. His elder brother Charles, who documented Bobby’s wartime experiences in his autobiography, outlived him by a decade.

Originally published in the March 2015 issue of Aviation History. To subscribe, click here.