Toby Esser, group chief executive, Cooper Gay

Guerrilla warfare...

I was held up at gunpoint in Colombia in 1990 by guerrillas in a case of mistaken identity. They eventually released me when they realised their mistake but until then I had a loaded machine gun mounted on the back of a truck pointing at my head.

Tennis ace...

I play a lot of sport particularly tennis which I take very seriously. Last year I competed in and eventually won the Arch Re tournament at Queens.

Suits you, sir...

I do love clothes and have 30 suits, most of them handmade, one for each day of the month. Each has a flamboyant lining however I do not wear them in rotation!

Fairytale of New York...

I began my career at Cooper Gay at the age of 19 and at the age of 24 spent some time in New York setting up a reinsurance intermediary.

High praise...

In 2007 I got an entry into the Sunday Times entrepreneur of the year where I was highly commended.

Toby Esser is group chief executive of Lloyd's broker Cooper Gay.

The 2025 Insurance Times Awards took place on the evening of Wednesday 3rd December in the iconic Great Room of London’s Grosvenor House.

Hosted by comedian and actor Tom Allen, 34 Gold, 23 Silver and 22 Bronze awards were handed out across an amazing 34 categories recognising brilliance and innovation right across the breadth of UK general insurance.
Many congratulations to all the worthy winners and as always, huge thanks to our sponsors for their support and our judges for their expertise.

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