It is a question many ask themselves and others. It is a question you may have asked when working away at your job or travelling on that packed bus or tube train. But what would you really do if you won millions on the lottery, horseracing, on the slots, or at a casino? 

Common answers include: 

• Give to charity; 
• Buy a new home; 
• Buy a new car; 
• Travel;
• Help my family;
• Buy new clothes;
• Buy expensive jewellery.

Mrs Herbert Will Look After His Cash 

History is full of those winners who either spent all their winnings, did something wonderful with them, or disappeared into anonymity. Here are just a few of those stories that made the news over the last century. 

In 1949, a man from Bristol won £73,000 on the pools. A British Movietone news reel shows pools winner Mr. and Mrs. Herbert getting advice from Mr. Emilio Scala, who had won £300,00 on the Irish sweepstakes. 

His advice was:

• Do not let it worry you 
• Give your children a good education 
• Above all, keep your head 

When asked what he was going to do, Mr. Herbert said, “I don’t know, it is a bit of a shock. I haven’t had time.” 

Mrs Herbert interjected quickly and said: “I can tell you what he is going to do. I have looked after him and his money for 17 years and I think I can look after his £73,000 for him.”  

A Shakespearean Tale of Deceit and Death 

Mrs Herbert no doubt honoured her promise to look after Mr Herbert’s cash. It was not the case for Abraham Shakespeare, a $30 million winner in the USA.

Abraham Lee Shakespeare won a $30 million lottery jackpot in Florida, receiving $17 million in 2006. In 2009, his family declared him missing, and in January 2010, his body was found buried under a concrete slab in the backyard of an acquaintance. 

Dorice "Dee Dee" Moore was convicted of his murder and is now serving life in prison. Moore claimed that he was killed by drug dealers and then said her son had killed him.

The Common Thread is to Spend, Spend, Spend

In 1961, Keith Nicholson won the pools. Britain would be unrecognisable to Gen Z.

The average wage was no more than £20 to £30 a week. A win of £155,000 would have been equivalent to £ £4,323,939.41 in today’s money. The cost of an average house was £2,006, compared to £211,000 today. 

In black and white TV footage (that’s sans colour for our younger readers), Keith and his wife Viv were shown in and outside their humble home in Castleford, West Yorkshire, with their three children at the time. They looked as one would expect, happy but shocked.   

The world-famous journalist Alan Whicker interviewed 25-year-old Viv in 1966.

Whicker was brilliant television viewing. He visited the pools checking centre in Liverpool and told the story of how the hundreds of ladies who checked for winners each week received £10 a week wages. 

When he pointed this out, a manager said that the girls were not jealous if they discovered a winner, just happy.   

Pools Winner Struggled with Depression and Alcohol Issues 

When Alan Whicker interviewed Viv Nicholson, she looked incredibly miserable, but she was brutally honest about how money had changed her life. Her husband had died in a motoring accident in 1965 and left her with a huge tax bill. She was eventually declared bankrupt. 

Keith and Viviene Nicholson Celebrate Their £152,000 Pools Win in 1961. (Image: Mirrorpix / Alamy)

Viv struggled with depression and alcohol issues and moved to Malta. She was deported from there following a fight with a police officer. 

Viv married a further three times and tragedy followed her. She told the BBC in 2011 that she had ‘no regrets’ over her spend spend spend philosophy.  

When asked what she would do with the winnings, Nicholson famously said: "Spend, spend, spend."

Viv, a former factory worker, did not disappoint, spending the cash in three years. She bought luxury cars, jewelry, and a ranch style home. Viv’s spending spree became the title for a musical about the pools her life. She died in hospital in 2011 with her sons at her side.  

UK’s Biggest Winner Blew £100,00 a Week 

Colin Weir from Scotland managed to spend most of his £50 million lottery winnings he won in 2011 over eight years until his eventual death in 2019 from sepsis, aged 72.  

Weir spent his money on:

• A football Club 
• A fleet of cars 
• Racehorses 
• A luxury home 
• Divorcing his wife 
• Jewellery 

Weir can be likened to the modern-day Viv Nicholson. Despite what anyone says prior to winning a huge jackpot, some things never change and we all like to spend, spend, spend.