Although there are other towns in the country that lay claim to the origin of the Dick Whittington story, Whittington which can be found 3 miles away from the town of Oswestry on the Shropshire border is a strong contender. The legend locally is connected to Shropshire through the Fitzwarine family and their ownership of Whittington castle. Dick is said to have travelled from his home near Ellesmere to London to seek his fortune.
After his long walk he managed to get employment in the home of Sir Ivo Fitzwarine (cousin to the Fitzwarine family who owned Whittington castle). Perhaps he had his apprenticeship papers to allow him to work for the Mercers company in London or his letter of introduction which enabled him to work for the Fitzwarine family. Whatever his poor start he ended up marrying Alice Fitzwarine the daughter of Sir Ivo his boss.
It is believed that Richard Whittington 1354-1423 was a medieval merchant and a politician.He is also the real life inspiration of the English folk tale of Dick Whittington and his cat. He was four times Lord Mayor of London, a member of parliament and a Sheriff of London. In his lifetime he financed a number of public projects, such as drainage systems in poor areas of medieval London, and a hospital ward for unmarried mothers. He bequeathed his fortune to form the charity of Sir Richard Whittington, which, nearly 600 years later, continues to help people in need. Despite knowing three of the five Kings who reigned during his lifetime, there is no evidence he was knighted.
Whittington died in March 1423. In 1402 (aged 48) he had married Alice, daughter of Sir Ivo Fitzwarin of Wantage in Berkshire but she predeceased him dying in 1411.