At the end of the movie The Man Who Shot Liberty Valance a reporter says, “when the legend become fact, print the legend.” While that might make great theater, it is an issue for historians. How do you separate legend from fact? Can they be separated? Most historians look for empirical evidence but this kind of “proof” is not always available. Even this type of “evidence” is not always accurate leaving historians to depend a good deal on circumstantial or the preponderance evidence to draw their conclusions.

Staten Island, like any other region, has its own share of legends and folklore. Some are easy to dismiss others are not. One of the most enduring stories surrounds how Staten Island became part of New York instead of New Jersey.

Mayors and even scholars have repeated the story of a boat race with Staten Island going to the winner. Even the venerable New York Times published stories on March 8, 1903 and again on September 18, 1921 recounting the tail of how a British Captain named Billopp saved Staten Island for New York. While a great story is it true? Leng and Davis had this to say about the legend, “We have found no contemporary record to prove the statement; nor, on the other hand, any other sufficient explanation of the favors so bountifully bestowed upon him.” OK, there is no “empirical evidence” so let us take a look at what evidence there is.

In actuality, the border between New York and New Jersey has been disputed for hundreds of years. The latest dispute was settled by the U.S. Supreme Court in 1998.

When the Dutch sailed into New York harbor, Staten Island was inhabited by the Lenape Indians, a New Jersey based tribe of the Delaware Indians. In 1630, the Dutch West India Company gave a patent or land grant to Michael Pauw for land on the western side of the Hudson River, from Hoboken south including Staten Island. Around the same time Pauw also secured a deed from the Indians for Staten Island.

In 1664, the English sail into New York harbor and took control of New Amsterdam for Great Britain without firing a shot. The King of England, Charles II, gave a patent to his brother James, the Duke of York for land in the new colony – New York.

The Hudson River would be the border between the two British Provinces (New York and New Jersey), however that did not settle the various land claims on the islands that populated the harbor such as Liberty Island, Ellis Island and Staten Island. Multiple Indian treaties and conflicting land grants created during the political struggle with the Dutch only added to the confusion particularly since historically Staten Island belong to the Dutch equivalent of New Jersey.

Why was the Duke of York so eager to settle this dispute? While Staten Island was rich in natural resources, it may very well have been an effort to control the access to New York’s harbor. If two different provinces controlled the narrows (New Jersey via Staten Island and New York via Brooklyn), is may well lead to disputes and competing taxes/tariffs on goods entering and leaving the port of New York.

To settle the dispute, the Duke decreed that any island in the harbor that could be circumnavigated in 24 hours would belong to New York. The Duke of York contracted Christopher Billopp with the task of circumnavigating Staten Island. As the story goes, Billopp embarked in his ship, the Bentley, and successfully completed the trip in about 23 hours in 1675. One year later, the Duke bestowed upon Billopp a large land grant that would eventually reach 1,600 acres. The grants are documented unfortunately there is no reason stated in the records why such a large grant was given to Billopp.

However, how does one explain why a relatively undistinguished sea captain was given the second largest land grant on record, second only to Governor Dongan’s (5,100 acres); this at the same time that properties on Staten Island ranged from 8-275 acres.

In absence empirical evidence, one can only draw conclusions based on circumstantial evidence: 1. Geographical location of Staten Island. If you draw a line south through the Hudson River, Staten Island lies to the West and historically it belonged to “New Jersey,” 2. The potential economic benefit for controlling both sides of the harbor, and 3. The unusual size of a land grant to an otherwise obscure and undistinguished sea captain, second in size only to that of the royal Governor the year following the alleged “race”.

In 1923, a New Jersey scholar by the name of James C. Connolly, presented a paper before the New Jersey Historical Society entitled How New York Acquired Staten Island. Much of the following information comes from his nine-page report.

I believe the story is true. You can draw your own conclusion.