Robert Dreghorn was one of the richest men in Glasgow at the end of the 18th century. He owned an estate at Ruchill, had a yearly income of 8,000 pounds, a fortune at the time, and an impressive mansion, one of the finest in the city. Despite his great wealth, he was a bit of a miser and it required a Court of Session ruling to enforce him to contribute to the Glasgow poor rates.

His greatest claim to fame, however, was his 'superlative ugliness', which resulted in him being known as Bob Dragon, the 'ugliest man in Glasgow', The following description of him is given: 'he was tall and lean, with a head of enormous dimensions and the strangest and most repulsive aspect. His nose lay almost flat against the side of his face, he was blind in one eye and squinted with the other and his skin was dreadfully ploughed and furrowed by smallpox, some of the marks being as large as coins'. He served a the Boogie Man for Glasgow mothers when they wanted to quieten their children: 'Bob Dragon will get you'.

Despite his 'ugly visage', he was one of the great dandies of Glasgow and was almost modishly dressed in a long black coat with a powdered wig and pigtail tied with a black bow. He always carred a walking cane which seems to have been mainly used to chastise children who would follow him. His main source of amusement was to 'perambulate the streets, particularly the Trongate and Argyll Street, and follow every handsome female that took his fancy in the course of his strolls'. This was a source of great amusement to the people of Glasgow. Bob Dragon always kept at a respectful distance from the ladies who were the subject of his pursuit and most of them took his interest good humouredly, or as a compliment to their superior beauty.

It was suggested that his behaviour was due to an 'eccentric mania'. However, sadly, he killed himself in 1806. After his death his house had the reputation of being haunted and remained deserted for many years.