He probably acquired the hotel as a part of a property purchased from John Anderson in 1836. At that time it was called the Sprig of Shillalah and was licensed to William Bergan. A record survives of an agreement signed in 1838 where the lease for the hotel is signed over to Robert Henderson, with Bergan remaining as the lessee.
When Bergan died late in 1841, Robert advertised in the newspaper for a new lessee (see advertisement above right). A few months later Jeremiah Callaghan transferred the licence of the Dove Inn from its former site in George Street to Robert's Erskine Street site, replacing the Sprig of Shillalah. But Callaghan was then declared insolvent in August 1843. The Courts appointed Henry Smith as the new licensee.
The name Henry Smith rang a bell with me, but it took a while for the penny to drop. Robert and Catherine Henderson had taken in an orphan child named Sarah Murray around the time they moved to Brisbane Water. Sarah was grown up, but still with the family when they moved to Sydney in the early 1840s and Robert was a witness at her marriage in August 1843. Her new husband was the same Henry Smith and they were married in the same month that Henry became the licensee at the hotel! According to Sarah and Henry's descendants, Henry was a shoemaker who had a shop on the corner of Erskine and Sussex Street (probably within the Dove Inn). Henry Smith was virtually a son-in-law to Robert Henderson, having married his foster-daughter.
When the next license is issued for the Dove Inn in May 1844, the licensee is Robert Henderson. It looks to me that Robert tired of unstable tenancies and when Callaghan went bankrupt, he put his son-in-law in as the licensee while he put his affairs in order and took over the license himself when it came up for renewal.
The pattern was repeated when Robert opened a new hotel just down Erskine Street from the Dove Inn. The first licensee of the Clarence Hotel was Henry Smith in 1852. Then Robert's son, Robert jnr took over the license when he turned 21.
Robert retained ownership of both hotels until he died and they were both included in his Will. He sacked his son Robert jnr as licensee when he deserted his wife, installing the deserted wife Hannah as licensee in 1860. It seems significant, to me at least, that Robert left the hotels to his grandchildren (the children of Robert jnr and Hannah), and not to either of his sons. Perhaps he didn't trust his boys after their antics in early adulthood.
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