One of the earliest references to a permanent crossing is found in an 1864 article from The Brooklyn Daily Times, reporting on the local Board of Aldermen's provision of $4,000 (equivalent to $77,923 in 2023) for the construction of a moveable bridge.

[13] After a request for proposal process which specified an iron bridge with either a stone or wooden substructure, a construction contract was awarded in July of the following year.

[16] The project's completion was formally accepted by county Supervisors on July 30, 1890[17] at a final cost of around $70,000 (equivalent to $2,373,778 in 2023), including the bridge's rebuilt approaches.

[20] Installed some time later, electrical machinery which could open and close the span in around "half a minute" was far more advanced than most of Brooklyn's other man-operated moveable bridges.

A significant controversy developed just eight years after its opening when local businessmen, represented by Congressman Charles G. Bennett, secured federal funding for dredging Newtown Creek to the tune of $275,000 (equivalent to $9,325,556 in 2023).

The agency, which would soon gain federal authority over all domestic waterway navigability with Congress' passage of the Rivers and Harbors Act of 1899, notified the City of its position in a letter:[22] "Whereas the Secretary of War has good reason to believe that the bridge over the East Branch of Newtown Creek, as Grand Street, Brooklyn, is an unreasonable obstruction to the free navigation of the said Newtown Creek, on account of the location of its piers and abutments and the narrowness of the draw opening, it is proposed to require the following changes to be made in the said bridge by April 1, 1900 to wit: The reconstruction of the bridge, with a width of forty feet, so as to make the west abutment not more than five feet beyond the harbor line, with a clear width of draw opening of not less than seventy-five feet, measured on the line of the bridge, and with the west abutment as far north and the east abutment as far south as the limits of the width of Grand Street will permit.

On April 21, 1899, the New York City Board of Estimate under Mayor Robert Anderson Van Wyck authorized bonds worth $200,000 (equivalent to $6,782,222 in 2023) for construction of the third Grand Street Bridge.

[25] According to a campaign ad, the measure was one of several concurrent public works in Brooklyn (including the Williamsburg Bridge) totaling over $14,904,000 (equivalent to $545,844,096 in 2023) worth of investment.

In a stroke of irony, it opened on December 26, 1902, the very same day that its predecessor re-opened to the public, just downstream, in a second life as a temporary crossing supporting construction of the Vernon Avenue Bridge.

[35] While Newtown Creek (and the new bridge) saw heavy use by maritime traffic through the early and middle decades of the 20th century, a greater trend toward highway and rail transportation in the postwar era also correlated to fewer drawbridge openings as time progressed.

Due to minimal usage, the Coast Guard amended federal regulations in 2000 to require a full 2 hours of advance notice for any Newtown Creek drawbridge openings.

In the spring of 1894, a large fight broke out between county law enforcement and workers of the Brooklyn City Railroad when a construction permit dispute turned violent.

According to a front-page report in The Standard Union newspaper, the railroad long-intended to install electrified trolley wires on the second Grand Street Bridge, but had failed to obtain permission from municipal engineers of Kings and Queens counties.