Cass Gilbert won the competition to design a new complex a few blocks from the old city hall building (since demolished) on West Main Street.

It is possible that they reflect a renewed interest in Lincoln in the wake of the centenary of his birth or the 50th anniversary of his death, both recent occurrences at the time of the complex's construction.

The five buildings in the complex cover a 4.4-acre (1.8 ha) area of Grand and Field streets on the south edge of downtown Waterbury, just north of the Interstate 84 viaduct.

A large main block faces the street, with two projecting rear wings on the south housing the police and fire departments.

Large fluted composite pilasters divide each bay, set with recessed nine-over-nine double-hung sash and projecting cornice caps in the pavilion and full round-arched windows on the ends.

A rear entry with sidelights topped by teardrops and an elliptical arch with fanlight, all of leaded glass, opens into the east-west central hallway.

[2]: 5 The hallway is sided in Vermont marble with carved panels featuring a fleur de lis pattern at the base, supported on eagle brackets and divided by pilasters with oak and acorn capitals.

[2]: 5–6 The front lobby is also lit from the rear by a six-over-six double-hung sash set with leaded and stained glass, opaque on the bottom but with a cartouche and swag on top.

The first story is, like City Hall's marble, rusticated, with the bays on the inside of the wings and the center pavilion made a series of segmented arches to give them an arcade appearance.

[2]: 12 The second story windows are also sash, set in rectangular openings with sills and cornice caps on consoles topped with rosettes or oval patera.

At its landing is a multilevel stained glass window, with urns, foliate and architectural motifs flanking a central panel with another quotation from Lincoln: "Go forward without fear and with manly heart."

[2]: 14 The former Waterbury National Bank Building, now headquarters for Junior Achievement of Southwestern New England, is located on the southeast corner of Field and Grand.

A stringcourse of header bricks laid vertically creates a springline for the round arches with keystones that enclose the second floor windows.

Another stair, rising from the rear entrance, was designed to be used by those served by the charities housed in the building, and thus climbs to the third floor in short, gentle flights.

The doorway is recessed in a brick arch with marble keystone, carved with an oval chrysanthemum patera, and impost blocks paneled on the outer facings and autographed on the inner ones.

The original light fixtures, molded milk glass globes hanging from brass chains, also remain although some were damaged by plaster falling from the ceiling.

[2]: 19 Gilbert took as his main inspiration for City Hall the house designed in 1772 by Robert Adam for Sir Watkin Williams-Wynn at 20 St. James Square in London.

"I have been studying a number of English examples of the Georgian period", he wrote to a friend, "and find so many in which the material was all brick or stone that I am justified in quoting this one as typical."

He had wanted the facing to be entirely marble as well, but the city insisted on brick and stone, an alternation which Gilbert had felt would be disharmonious given the narrow window spaces.

"...[I]t would seem a presumptuous attempt on the part of private citizens to imitate and share the dignity of city hall", Chase wrote Gilbert.

The architect and the brothers then toured Manhattan looking for other ideas, and left it to Gilbert to come up with his ultimate solution, limestone deployed in a more Renaissance Revival style.

He in turn persuaded the Chases to accept the wrought iron fence out front, using the J.P. Morgan Library in Manhattan as an example of how that element could be successful.

Architects McKim, Mead and White gave the New York, New Haven and Hartford Railroad a significant Second Renaissance Revival building, capped by a 240-foot (73 m) clock tower based on the Torre del Mangia that has since become a symbol of the city.

The three did establish a productive relationship, and Gilbert quickly laid out a park for the small block opposite the train station and designed a fountain for it as well.

Construction began on City Hall in 1912, shortly after the old building had burned,[2]: 25  when the Grand Street site narrowly won in a referendum.

Scrap metal was piled up on the entourage in front of City Hall, and the tower was surrounded with scaffolding so that air wardens could keep watch from it.

Other tenants of the space in those years included the city's Adult Probation Department, Legal Aid, and the local Chamber of Commerce,[2]: 35  which was headquartered in the Power House next door.

[7] By the early 21st century, most city government functions, including the mayor's office and council meetings, had been moved across the street to the Chase Building.

The Fire Department eventually ordered all government bodies out of the building save the City Clerk's office, which could not function without access to the records vault.

Aldermen from the Independent Party who believed the public should decide on a spending program that large succeeded in getting the issue put to a referendum in 2007, which defeated it.