WI: Long Island Statehood

What is the earliest and most likely time period/reason for Long Island to become a state, either because it was a separate colony prior to independence or post-independence. Do you think it was possible earlier on in the country's history, and if so, how do you think it could have happened?
 
It's going to be hard for New York to agree to let it go.

Perhaps the administrative divisions of British North America are drawn differently following the dissolution of the Dominion of New England, and Long Island becomes a Crown colony along the lines of Rhode Island?
 
Here's an idea: the Revolutionary War ends with loyalists in control of Long Island, but not Manhattan or the mainland. For some reason (maybe Long Island attracts and holds onto a large number of Tory refugees?), the peace maintains this state of affairs, with an international border established along the East River. The US acquires Long Island later and doesn't reattach it to New York.
 
Hmm...I like that idea. Both of them actually.

One idea I had was that Long Island is originally given to Connecticut by the crown as per the original dispute in the mid-late 1600s (The border would roughly correspond with the OTL Nassau County-Queens border). You now have, after independence a metropolitan Connecticut in the north and a largely rural Long Island in the south. Somewhat similar to the enlarged Massachusetts of the period. Perhaps as part of a compromise between North and South during the Antebellum years, Long Island gains statehood in exchange for a slave state gaining statehood.
 
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