Joseph Dainty almost certainly never lived on Park Lot 33, but his rights to the property held it in abeyance for nearly four years. The records surrounding the ownership of Park Lot 33 tell us all we know of the mysterious Mr. Dainty.
The first step in land ownership in Upper Canada was to request it with a petition—and Joseph Dainty petitioned twice.
Joseph’s first petition, addressed to Lt.-Gov. John Graves Simcoe, was written on July 10, 1793. It explains that Joseph was a “native of Great Britain” and requests a Town Lot at Toronto and a 200-acre farm lot close by. Note that he called the place Toronto—just five weeks later it would be officially renamed with the very British moniker “Town of York”. Joseph’s request for land was granted three days later on July 13. There is no indication of where Joseph was when he wrote this first petition, but given the timing of the petition and its quick approval at Navy Hall, Newark (now Niagara on the Lake) is the most likely place.
However, by August 9, 1793, when he signed a second petition, Joseph Dainty was at “York”. Did he perhaps arrive with Lt.-Gov. Simcoe’s party on July 30 on the Mississauga, or a few days later on August 4 on the supply ship Onondaga? Was he part of the advance party of Queen’s Rangers? None of the records I’ve found show any military rank or connection with the Queen’s Rangers—so I think that option is unlikely.
Why did he go to York? Was Joseph simply seeking opportunities, or was he invited along because of some special skill or connection to Simcoe or his senior officers? Joseph Dainty’s second petition and the date of its acceptance lend some credence to the theory that he was invited to York.
On August 9, 1793, Joseph petitioned for Park Lot 33 and the irregularly shaped piece of property directly south of it on the lakeshore—the “broken front”. The petition gave no particular reason why Joseph felt he deserved the parcel, other than he was willing to improve it “immediately.” Had he been given some indication that his request might be favourably received?
The petition was read at the Executive Council meeting in York on September 2, 1793, and Joseph was granted Park Lot 33, but not the broken front. September 2 was just one day of a marathon session that saw the granting of most of the prime lots in and around the new Town of York. (Twenty-four Park Lots were granted on September 4 alone.)
The fact that Joseph Dainty’s name was included in this important group of early grantees says something about his status—we’re just not sure what.
Was Joseph present in York so that Deputy Surveyor Aitkin could inform him and locate his lot “immediately” as ordered by the Executive Council?  The records are silent about Joseph’s whereabouts until 1796.
In April 1796, Lt.-Gov. Simcoe commissioned a committee of the Executive Council to report on the state of settlement in and around the Town of York. The “York Report” as the result came to be known was presented in April and May of 1796. The York Report listed Joseph Dainty as the grantee of Lot 33 in the First Concession of York Township—and “Dead”.
Seven months later, Lieutenant Colonel David Shank, already a Park Lot owner, petitioned for Park Lot 33 as part of the “military lands” he had been promised. His petition, dated January 26, 1797, acknowledged that the lot had been “formerly granted to Mr. Dainty deceased”.
But there was a snag. The deputy surveyor reported that Joseph Dainty had “improved upon” his lot. Peter Russell, Administrator of Upper Canada in Simcoe’s absence, asked Surveyor General D.W. Smith to investigate further.
Smith reported back on March 10, 1797, that the improvements were not on Park Lot 33, but on the broken front, where an un-named blacksmith “formerly belonging to the Indian Department” had built a shop prior to the 1793 grant to Joseph Dainty. The blacksmith had lost his job with the Indian Department and “sold his pretensions” to Mr. Hahman also a blacksmith.
D.W. Smith goes on to say that Joseph Dainty had become sick soon after he was granted Park Lot 33. He died at “Fitzgeralds on the East side of Niagara River”. This information was obtained by Deputy Surveyor General William Chewett from Mr. Heron “who professed to know Mr. Dainty very well.”
Smith’s report satisfied Peter Russell and the Council, and Park Lot 33—without the contentious broken front—was granted to David Shank on March 14, 1797.
 Upper Canada Land Petition: Toronto, 1793, Joseph Dainty, Petition 1 (Library and Archives Canada/ Executive Council of the Province of Upper Canada fonds/ Vol. 149/ Bundle D 1/ Microfilm C-1742)
 On August 24, 1793, after receiving word of the Duke of York’s success at Famars, Simcoe ordered a Royal Salute and named the settlement York.
 Upper Canada Land Book A, 1792–1796, p 117 (Library and Archives Canada or Archives of Ontario microfilm C-100)
 Fryer, Mary Beacock and Christopher Dracott. John Graves Simcoe 1752–1806: A Biography. Toronto: Dundurn Press, 1998, p 163.
 Upper Canada Land Petition: Toronto, 1793, Joseph Dainty, Petition 16 (Library and Archives Canada/ Executive Council of the Province of Upper Canada fonds/ Vol. 149/ Bundle D 16/ Microfilm C-1742)
 Upper Canada Land Book C, 1797–1802, p 327 (Library and Archives Canada and Archives of Ontario microfilm C-101)
 ibid. p 329
 Upper Canada Land Book B, 1796–1797, p 205 (Library and Archives Canada and Archives of Ontario microfilm C-101)
 ibid. p 206
 Report book, Crown Land Dept, 1795–1799, p 88 (Archives of Ontario RG 1 A-II-1 vol 1, now known as RG 1-12-1-2, microfilm MS 3696)
 Probably John Henry Kahman who appears on inhabitants lists in York from 1797 to 1808 (Mosser, Christine. York, Upper Canada Minutes of Town Meetings and Lists of Inhabitants 1793–1723. Toronto: Metropolitan Toronto Library Board, 1984)
 Probably Samuel Heron, who acted as an agent in a land transaction for John Henry Kahman in 1797, and whose Niagara connections may have provided information about Joseph Dainty’s demise (Crown Land Department correspondence, Archives of Ontario RG 1 A-I-6 box 2, now known as RG 1-1-2-4, microfilm MS 7522)
 Upper Canada Land Book B, 1796–1797, p 250 (Library and Archives Canada and Archives of Ontario microfilm C-101)