Bill was born in Chelmsford on 4th December 1910, the second of three children of Hale Westrop Bolingbroke and Alice Grace Bolingbroke (nee Bellamy), His father had been born in Chelmsford in 1880; his mother in Gorleston, Suffolk in 1882. The couple had married in Great Yarmouth, Norfolk on 18th April 1906.

Bill’s siblings were Barbara Grace Bolingbroke (1907-1990) and Margaret Ann Sally Bolingbroke (1816-1991).

In 1911 the census recorded four month-old Bill living with his parents, elder sister, a servant, and two visitors at The Hutch, in what is now Old Court Road, Chelmsford. At the time Bill’s father was a draper, connected with his brother Stanley in the family business Bolingbroke and Sons (later to develop into Bolingbroke and Wenley).

Bill was educated at King Edward VI’s Grammar School in Chelmsford from 1926 to 1930 and pursued a career as an automobile engineer, Her learned to fly and on 28th May 1935 he gained his pilot licence.

On 6th November 1935 Bill was granted a short service commission as Acting Pilot

The funeral of Mr. Bolingbroke took place on Wednesday. The service at All Saints' Church, Springfield, was attended by a large and representative gathering of sympathisers. The Rector, the Rev. R. C. Collwvn Hargreaves, officiated, and the choirboys were in attendance. Mr. F. Harnack was at the organ."

On 6th November 1936 Bill was confirmed in the rank of Pilot Officer. On 20th November 1937 he was promoted to Flying Officer and on 20th November 1938 he was promoted to Acting Flight Lieutenant.

In April 1939 Bill was awarded the Distinguished Flying Cross for gallant and distinguished service in Palestine. A Chelmsford newspaper reported:

"CHELMSFORD OFFICER HONOURED. GALLANTRY IN PALESTINE.

Flying-Officer (Acting-Flight Lieutenant) Hale Winter Bolingbroke, son of the late Mr. Hale W. Bolingbroke, and of Mrs. Bolingbroke, of The Hutch, Springfield, Chelmsford, has been awarded the Distinguished Flying Cross for gallant conduct while on active service in Palestine.

The announcement of the award is contained in the 'London Gazette" as follows: "Flying-Officer (Acting-Flight Lieutenant) H. W. Bolingbroke, on March 11th, answered call foi air assistance at Zemal. Although his aircraft was subjected to heavy rifle fire from dense coverage, he continued to attack the armed rebels with outstanding courage and determination. The difficulties in taking action in a deep wadi necessitated exceptional flying and daring. "This officer has been in action against the enemy on numerous occasions, and has shown conspicuous gallantry and devotion to duty.'

The Mayor and Mayoress of Chelmsford (Cllr. and Mrs. J. T. Bellamy) have sent Flying-Officer Bolingbroke a cable of congratulation on behalf of the Borough."

After the outbreak of war later in 1939 Bill remained in the Middle East.

On 16th June 1940, when aged 29, Bill was killed in a flying accident in Egypt while serving with 33 Squadron. He had no known grave and is commemorated on the Alamein Memorial in Egypt.

A Chelmsford newspaper reported:

"FLYING-OFFICER S DEATH.

News has been received of the death while flying on active service in June of Flight- Lieutenant Hale Winter (Bill) Bolingbroke, D.F.C., only son of the late Mr. Hale W. Bolingbroke, and of Mrs. Bolingbroke, of The Hutch, Springfield, Chelmsford.

Flight- Lieutenant Bolingbroke, who was 29, and an old boy of Chelmsford Grammar School and King Edward's School, King's Lynn, had been with the R.A.F. for about five years, showing outstanding promise during his training, and spending much of his commissioned career abroad.

In April, 1939, as a Flying-Officer (Acting-Flight-Lieutenant) he was awarded the Distinguished Flying Cross for gallant conduct while on active service in Palestine. The announcement of the award in the London Gazette" was as follows: 'Flying-Officer (Acting-Flight-Lieutenant) H. W. Bolingbroke on March 11th answered a call for air assistance at Zemal. Although his aircraft was subjected to heavy rifle fire from dense coverage, he continued to attack the armed rebels with outstanding courage and determination. The difficulties in taking action in a deep wadi necessitated exceptional flying and daring. This officer has been in action against the enemy on numerous occasions, and has shown conspicuous gallantry and devotion to duty."

A cable of congratulation on behalf ot the Borough of Chelmsford was sent to Flight-Lieutenant Bolingbroke on that occasion. Much sympathy is felt for the bereaved mother and two sisters. The late Mr. Haie Bolingbroke, father the deceased officer, was well known and highly esteemed Chelmsford, being a partner (with his brother, Aid. S. L. Bolingbroke) in the firm of Messrs. Bolingbroke and Sons, Ltd.. High Street, Chelmsford.

Flight-Lieutenant Bolingbroke was engaged to Miss Barbara Diver, daughter of Mrs. Diver, of Walton-on-the- Naze, and of the late Mr. C. Diver, formerly manager of Lloyds Bank at Chelmstord."

Bill left an estate of £2,372 6s. and 6d, with probate granted to his mother. She was to die two years later. Bill is commemorated by the Springfield War Memorial at All Saints' Church.

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Hale Winter ‘Bill’ Bolingbroke was born and raised in Chelmsford and educated at the town's grammar school between 1926 and 1930. Rather than join his famiily's well-known drapery store he followed a career as an automobile engineer. He gained his pilot's licemce in May 1935 and soon afterwards joined the Royal AIr Force as a pilot. He was awarded the D.F.C. in April 1939 for distinguished service in Palestine. Afther the outbreak of war he remained in the Middle East and was killed in a flying accident in Egypt in June 1940. At the time he was engaged to marry. His home was in New Court Road.

Officer on probation with the Royal Air Force, with the service number 37442.

Bill’s father died on 1st August 1936 leaving an estate of more than £6,500. A Chelmsford newspaper reported:

"DEATH OF MR. HALE W. BOLINGBROKE WELL-KNOWN CHELMSFORDIAN

We regret to record the death, which occurred at his residence, The Hutch, Springfield, Chelmsford, on Saturday morning, of Mr. Hale Westrop Bolingbroke, one of Chelmsford's best known tradesmen.

Mr. Bolingbroke, who was 56, had been ill about three weeks, suffering from brain pressure. He was son of the late Mr. G. J. Bolingbroke who died only last year, and with his brother, Mr. Stanley L. Bolmgbroke (who is a member of Chelmsford Town Council), carried on the business of Messrs. Bohngbroke and Sons, Ltd., High Street, Chelmsford, ladies' outfitters drapers, etc.

Mr. Hale Bolingbroke was a most capable business man, greatly esteemed by circle friends. At one time Mr. Hale Bolingbroke was an active worker at All Saints' Church, Springfield, and attended the church's recent fete at Springfield Place.

As a young man he was a smart member of the old Loyal Suffolk Hussars (who preceded the Essex Yeomanry). During the Great War he served in the Artists' Rifles and became a Sergeant-Major at Gidea Park. He was also for a time a member of the Chelmsford Volunteers, and a prominent supporter of the Old Volunteers' Association, regularly attending the annual reunion. He served as President of the Association last year. Much sympathy is felt for the widow, one son, and two daughters.