_83360125_krays2 A Reggie Kray letter
Image via BBC

The letters were written whilst Reggie was in HMP Parkhurst prison, Isle of Wight, under a life sentence for murder. The almost illegible handwritten letters were sent to his friend Maureen Baker and are expected to reach £500 in the saleroom.

The letters will go under the gavel at Wiltshire auctioneers Henry Aldridge and Son tomorrow.

Auctioneer Andrew Aldridge commented: "The letters offer a fascinating snap shot into the mind of one Britain's most notorious gangsters.''

"One sentence in particular is fascinating, 'I never did receive the letters in the guard house, if I had it may have changed the direction of both our lives, but it is no good to look back.''

"This letter represents a real sliding doors or 'what if' moment of history on how his life could have been so different if he had have received the letters he mentioned."

2301036 The Kray Twins
Image via vervesplash.net

The letters have been consigned by a relative of the now deceased Mrs Baker. This is not the first time Kray pieces have hit the saleroom, in 2010 over 160 never-seen-before letters and photographs sold for over £20 000 at auction, whilst in 2012 two paintings by each twin sold for £1 200.