WORCESTER Crown Court heard how Steven Smith targeted Mr Bennett.
Smith pretended he was interested in buying a car belonging to Mr Bennett's son, which was parked on the driveway of the pensioner's home in Meadow Road.
On his second visit in a month to the house, Smith wrote down a fake phone number for himself and grabbed the victim's wallet containing £120 and photographs of his wife who had died 14 years earlier, said Tim Sapwell, prosecuting.
The pictures were never seen again and, according to Mr Bennett's daughter Deborah Pullen, the theft badly affected him.
Smith, aged 26, of Suffield Close, Leigh Sinton, pleaded guilty to theft and was jailed for 18 months.
His record of 32 previous offences included 19 thefts, eight frauds, burglary, deception and handling stolen goods.
Judge John Cavell said he had posed as a genuine car buyer to steal "highly sentimental pictures which were lost forever".
He told Smith: "You acted through greed to get money and gave no thought at all about the affect your conduct would have on your victim.
"I accept that what happened afterwards was never intended, but can well understand why the victim's family say there was a connection."
Smith first approached Mr Bennett - who lived alone and needed a walking frame to move around his home - on June 27 last year, said Mr Sapwell.
He was invited in but left a phone number which was not able to be contacted.
Exactly a month later he called again, putting his parents' phone number on a piece of paper, but deliberately changing one of the digits in a bid to escape detection. When Mr Bennett's back was turned, Smith took his wallet off a sideboard.
Mr Bennett, who had worked at Kays and had other jobs all over the world, noticed it missing 20 minutes after he left. He died on November 12.
Detectives traced Smith because he left a fingerprint on the phone number paper.
Adam Western, defending, said Smith was ashamed of the mean offence which was carried out to feed his heroin habit.
He added: "Mrs Pullen speaks powerfully of the effect on her late father. The very serious effect that it had on him could not be reasonably anticipated by the defendant."
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