Sudden death of a very witty headteacher

Dr Stephen Winkley
Dr Stephen Winkley
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A popular recently-retired headteacher has died suddenly after a short illness.

Dr Stephen Winkley came out of retirement to take over the reins of the prestigious Rossall School and was so popular he stayed longer than he planned.

Dr Winkley came out of retirement at the age of 63 to take on the headship in 2008.

In the years that followed he was credited with transforming the Lancashire independent school, attracting record numbers of pupils and spearheaded a major investment programme.

He has been described as “a charismatic and strong head who had an undoubted impact on the history of Rossall School, leading it through a time of change and growth with great courage. “

A spokesman said: “He will also be fondly remembered for his approach to life, his insightful wit and occasionally eccentric dress sense - most notably his penchant for red shoes.

“Dr Winkley, with his incredible mind, love of people and great faith in the power of education was a very special man.

“He will be long remembered at Rossall and we shall miss him. Our thoughts and prayers are with his family and close friends at this time.”

Elaine Purves said: “Rossall was shocked and saddened by the news of Dr Winkley’s untimely passing. He will be greatly missed by all. He had a genuine interest in the pupils and their welfare and had an honest, warm personality. Dr Winkley’s witty weekly newsletters still have cult status.

“Throughout his career Dr Winkley was an inspiration to many and a truly gifted headmaster. But perhaps one of his most enduring legacies will be that he helped to turn around the fortunes of Rossall School. The School is now a flourishing beacon thanks largely to Dr Winkley’s transformational work.”

After more than 40 years working in the independent education sector and in 2011 he was presented with a Lifetime Achievement Award.

He started his career at Cranleigh in 1969 and 16 years later became second master at Winchester College, the last holder of the joint office of deputy head and master in college.

Married to Jenny, he had sons Leo and Mungo and his daughters, Imogen, Isabella and Jess. Mungo is a housemaster at Rossall School and head of EFL. His other son is headmaster at St Peter’s School in York.

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