James Keenan

WWII bomber pilot James H. Keenan’s high school yearbook envisioned a future in flight. “Jimmie is interested in aviation they tell us. Well, good luck to you old boy, but don’t forget your friends when you cross the Pacific by aeroplane.” Jimmie crossed not only the Pacific but also the Atlantic, Bay of Bengal, and Mediterranean as a pilot and flight leader during the war.

WINCHESTER – Six months after Pearl Harbor, the war in the Pacific was not going well for the Allies. Although a change in the tide of war was around the corner with the Battle of Midway, in May 1942 morale needed a boost.

The Allies had suffered many disastrous defeats. Winchester knew this well, for it hit home. The town lost LCDR Hugh Black, LCDR Lawrence McPeake, and RM Edmund Dunn when their ships were sunk, and it heard that Pvt. Anthony Duquette was taken a prisoner of war when the remaining U.S. troops on Corregidor in the Philippines surrendered to the Japanese.

Then, 75 years ago, came good news. The US Air Force had essentially taken out an enemy air base in Burma, and Winchester had its first aviation hero.

 Overnight on May 5-6, as a report from New Delhi printed in the Boston Globe stated, flights of U.S. bombers in India which were “striking to prevent Japan’s military consolidation of Burma for sustained offensive action against either India or China” had crossed the Bay of Bengal and attacked the Mingaladon airdrome in Burma.

A communique from Gen. Douglas MacArthur’s headquarters reported that enemy planes were all but wiped out in the attacks. This communique also named one of the lead pilots – Winchester’s James H. Keenan, WHS Class of 1929.

“Winchester has had its tragic news from the war,” The Winchester Star reported on May 8, 1942, “and now it has a chance to rejoice in the feat of its Jimmy Keenan, who as First Lieut. James H. Keenan led one of the two flights of the United States Army bombers that destroyed 40 Japanese planes and badly damaged 25 others in a big raid on Mingaladon Airdrome just north of Rangoon in Burma early Wednesday. Big fires were started that were visible 70 miles away.”

A year later, the town learned that Keenan was awarded the Air Medal for his efforts in Burma.

“For having flown heavy bombardment missions totaling more than 100 hours from March 6, 1942 to July 30, 1942, Capt. Keenan’s constant and untiring effort as the senior member of the combat team flying from bases in India has contributed much to the success of the many missions in which he has participated.”

Burma was only part of Keenan’s war. After he returned home on leave in October, 1943, the Star passed on a few personal anecdotes.


“Jimmy Keenan has been in the Army Air Forces for nearly four years. He has been decorated by Gen. Henry H. Arnold, Air Forces Commanding General and has flown from Bangor, Me., to Bangalore, India, and Bangkok, Siam. Among other exploits he is credited with flying a B-24 on one of the longest raids on record, a round trip of 2,850 miles in 16 ½ hours from an Indian base to strike at Bangkok.

“He and his crew had trouble opening their bomb bays on their longest flight and in working on them all forgot about a cluster of incendiary bombs they were carrying. When the big 500 pound bombs finally ripped open the bays, the incendiaries also went through the torn doors and exploded.

“Fortunately the plane cleared the flames or there might have been a different story to tell. Fortunately also was Capt. Keenan that he did not quite fall through an open bay while chopping away the doors that were cutting down the plane’s speed on its 1,400 mile return flight.

“Another thrilling experience Jimmy had was near the Andaman Islands where he expected to find two Jap tankers. Flying in at night at 2,500 feet, he found instead the whole Jap invasion fleet for Ceylon. His ship managed somehow to dodge the concentrated Nipponese fire, getting away with the loss of a left wheel and right flap.

“Jimmy’s adventures include a crash landing in Venezuela 80 miles from a telephone, flying British subjects out of Burma (he had as many as 55 women and children in his plane at one trip), bombing over the Mediterranean at Crete, Navarino Bay, Greece; and Tobruk; smashing Jap targets in India and meeting the famous Jimmy Doolittle after his epic Jap raid. His gyro stuck while he was flying low in clouds over Egypt and when he leveled out according to his instruments he went into a tight spiral, which he was lucky to pull out of. As he tried to land he burned out a brake and almost ground-looped.

“Taking off again, the plane ran out of oxygen at 32,000 feet. All he could do before passing out was put the plane in a dive and hope he’d come to in time to do something about it.

“He regained consciousness at 18,000 feet with the plane diving 330 miles per hour for Tobruk. ‘And of course,’ he added, ‘people were shooting at us!’”

After 17 months of warfare, Keenan returned to the US in late 1943 to assist in the heavy bombardment training program.

The making of a flyer

Born in New Jersey in 1912, Keenan spent his childhood in Cambridge, but his family moved to a home on Highland Avenue during his high school years.

“Jimmie is interested in aviation they tell us,” his yearbook stated. When interviewed by the Boston Globe, his mother said that ”Jimmie was always mechanically inclined” and that he and a friend in high school built a plane, with a motor taken from a motorcycle, “and it actually flew two or three times.” That adventure ended with a crash, but no one was seriously hurt.

For 10 years after graduation Keenan worked as a painter and carpenter and assisted his father in the insurance business, and he studied at MIT, all the while maintaining his interest in aviation. In 1939, he joined the Army Air Corps and received his wings at the Kelly Field Flying School in Texas in 1940. Before the country entered the war, he was given assignments at bases in Long Beach, Cal., and Bangor.

Married movie star

Before the war broke out, Keenan made the news, locally and nationally, when he married actress Anne Nagel.

Nagel, born Ann Marie Dolan in Malden in 1915, began appearing in movies in 1932. After being widowed in 1937, she was all set in July 1941 to go to the Dutch East Indies to marry a Navy man, but as the Globe put it, “Uncle Sam decreed: No women allowed.”

Having given up her contract with Universal Pictures, Nagel went east, touring in “The Hollywood Sweater Girl Revue,” which played in Boston, Providence, and New York. According to the Globe, a backstage romance with Keenan began in Boston (a later story said he met her at her home in Melrose) and continued in New York.

The day after the show closed in New York, Nagel went back to Boston and married Keenan on Dec. 4, 1941. A Municipal Court clerk performed the surprise ceremony, which required that the waiting period be waived and included only the bride, groom and two witnesses.

Following the ceremony, Nagel rejoined her vaudeville show. Keenan left for Langley Field in Virginia. Pearl Harbor followed three days after the wedding. Thus, while Nagel returned to show biz, Keenan went to war.

After the war Keenan moved to California. The marriage fell apart, and divorce proceedings began in 1951, to become final in 1957. During the 1950s, Keenan – then Lt. Col. Keenan – returned to active duty with the Air Force in Korea.

Keenan married again three times, his fourth wife being Harriet Lee (Pilkington) Wood, the widow of another Winchester veteran. After his death in 1993 in Florida, he was laid to rest in his wife’s family plot at Wildwood Cemetery.

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