Circling the walls of the Speaker's Office are images of former Speakers dating back to the adoption of the Massachusetts Constitution in 1780. The earliest, Caleb Davis, a wealthy merchant and revolutionary war patriot, hangs on the wall opposite the fireplace, at the upper left. Prints and photographs are clockwise around the room—seventy-four at present.
The display was first installed in 1899 and is updated after each administration. Images of the earliest Speakers were reproduced from a variety of sources including extant paintings, prints, and line drawings until photographs could be obtained directly from each sitter. There is a similar display of former Senate Presidents in that office.