From 1911, Cass Gilbert’s sketches of his father (top) and himself (bottom):

From the Woolworth Building lobby as completed in late 1912, the grotesque* of Gilbert holding a model of his building:

Given that the grotesque is wearing glasses but not a laurel wreath, a sketch much like the one on the lower right was used as the basis for that grotesque’s head. The grotesques were designed by a caricature artist named Tom Johnson, but I can easily see Gilbert wanting to have his hand in for the representation of himself.
The grotesques are all supposed to be related to the building’s design and construction. The two most famous are Gilbert and one of F. W. Woolworth holding stacks of nickels and dimes, but Gunvald Aus, the structural engineer for the building, is also there. I can say that’s far more public recognition than engineers usually get.
Obviously, there was no need for any of this. The exterior of the building has various animals, both real and fictional, as grotesques, and certainly that theme could have been continued in the lobby without in any way disturbing the gothic-architecture design. Someone, or more likely more than one person, thought this would be good fun, and 120 years later the joke still amuses people. The downside of trying to building a high-quality building is that even your off-hand jokes have to be of high quality or they will drag the whole thing down. I’ve never come across anyone who thought that the grotesques make Woolworth less serious as a work of architecture, but lousy-looking art in the lobby would certainly have had that effect.
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* The figures at Woolworth are grotesques rather than gargoyles as they serve no function.

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