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But Southern Cross Jewellers owner Michael Lee disputed the claim, and said he bought the watch from Mr McCaw legally and fairly.
Mr Lee had serviced Mr McCaw's Rolex a few times in the last decade, and had held it at his Princes St shop for the last two years to repair.
On December 2, Mr McCaw (83) went to the shop to see if his watch was fixed and was told it needed parts from England.
Mr Lee offered to buy the watch instead.
''I asked him [Mr McCaw] if he wanted to sell it and was prepared to pay $200 or $300 for it, but he said I could have it for $100. He was quite clear and happy with the sale at the time,'' Mr Lee said.
''I would have been happy to repair it and sell it back to him,'' Mr Lee said.
There was no receipt or record of the transaction.
Mr McCaw left the shop with $100, but a few hours later, when he told his daughter Caroline McCaw about the sale, he realised he had made a mistake.
The McCaws immediately contacted Mr Lee in an attempt to get the watch back.
Ms McCaw telephoned the jeweller that afternoon and asked for the sale to be voided.
She explained her father did not intend to sell the watch, that the gold alone was worth more than $100, and it was a family treasure with sentimental value.
She offered to buy back the watch, but she said Mr Lee refused.
The next day, Ms McCaw accompanied her father to the shop.
She said Mr Lee would not discuss the matter and asked them to leave the premises.
Mr McCaw handed Mr Lee a written letter, explaining his concerns and his intention to involve the police, which he subsequently did by lodging a claim of theft.
''Your purchase was illegal and void. I believe that I have been swindled, and require the return of the watch immediately,'' his letter stated.
Mr Lee said he dismantled the watch and sent it to England the morning after he bought it from Mr McCaw, and therefore, he did not have it to sell back.
Mr McCaw was not sure what his legal rights were in respect of the sale.
The Consumer Guarantees Act covered the buyers of products, and the Fair Trading Act related to the promotion and sale of goods, but it was unclear if either piece of legislation protected his sale of the watch and subsequent change of mind.
He had not heard from police since making a claim.
Mr McCaw said regardless of the legality of the transaction, he remained annoyed about the matter and worried something similar could happen to other elderly people.
''He [Mr Lee] took advantage of my confusion, and it annoys me because I've been in business all my life but I'm retired and I'm getting on a bit now. If I was younger and in full flight I would never have accepted that $100.''
His daughter said the incident amounted to elder abuse and her perception of Dunedin being ''an honest place'' was tainted.
''Ultimately, we've accepted the watch is now gone, but we don't want this to happen to other people. In this case, I've been here to help Dad, but in other cases elderly people might not have that support,'' she said.
Ms McCaw was helping her father explore his legal rights in relation to the case, and cited Lord Denning's unjust enrichment and inequality of bargaining power doctrines as possible means for protection.
Mr McCaw had worn the Rolex for more than 50 years after it was given to him in 1958, when he finished working as an accountant for a large British firm in Kuala Lumpur.
He said the watch had been valued at between $2000 and $10,000.
Mr Lee told the Otago Daily Times he had done nothing wrong, the sale was legitimate and fair, and it was unfortunate the McCaws were upset.
He said the Rolex was worth a few hundred dollars at best, and if repaired, would be worth no more than $1500.
Mr Lee said he did not use receipts because he had Mr McCaw's details.