John Osbaldiston had a brief moment of fame. Born c.1786, he was the son of Philip Osbaldiston, a baker in the High Street from 1776 at least. John entered the family business. At the age of 21 years (on 13 May 1807) he married Mary Primer, a minor one year his junior, by licence in Holy Rood church. Life changed in c.1809, when he purchased a whole ticket (most purchases were of a fraction of a ticket, down to one-sixteenth) in the state lottery. It netted a first prize of £20,000. Later legend had it that the number (4709) was given him by a young female who had a premonition of the win. John overnight became a gentleman. By 1813 he had acquired land at Botley Grange. In May 1817 he purchased the copyhold of a property at Crowd Hill, on the turnpike between Fair Oak and Winchester, including a newly-built cottage, malthouse, granary, stable, orchard and garden. Most conspicuously, he built shortly after his win the impressive Lottery Hall in Orchard Place, Southampton.
The prize inexorably melted away. The Crowd Hill land was mortgaged for £800 in 1818 and surrendered completely in October 1828. Lottery Hall, heavily mortgaged, was sold at auction in January 1836 for £2,790 - over £4,000 less than he had been offered for it a few years previously. The Hampshire Advertiser reported the former proprietor to be "scarcely above want", owing to "a few speculations, loans of extravagant interest unpaid, and want of a little common sense". He continued to live quietly in Orchard Lane until his death - unreported in local newspapers - in early 1839. His personal estate and effects were valued at less than £100. His wife Mary died on 12 August 1850 in Oxford Street.
The family bakery at 109 High Street was carried on until the mid/late 1840s by, successively, his brother Joseph (who strangely became bankrupt in 1815), his sister Mary, his niece Elizabeth Matilda and his second son John Henry (born October 1814). At the death of Mary in June 1842 the family owned the block 107 to 109 High Street. The business, under John Henry, moved to 11 Orchard Lane in c.1849 and subsequently, in c.1865, to 1 Oxford Street. John Henry Osbaldiston died at St Denys in July 1872.
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