The building, described as fireproof, was destroyed by a massive fire on January 9, 1912.–Wikipedia

File:Equitable Life Assurance Building 1870.jpg

First skyscraper because it’s the first building to come equipped with passenger elevators.  I can’t find any evidence for it yet, but I would wager Jake Schiff , and his Kuhn Loeb & Company, financed Japan in its war against Russia from this building.  What is for sure is that Schiff had offices in the giant shadow-casting monster that replaced it, New York’s first twin tower,

one where Schiff partly bankrolled the Bolshevik Revolution.  Larry “Pull It!” Silverstein owns the property today.