Designed by Henry Kreis, the obverse depicts the showman P. T. Barnum, who was one of Bridgeport's most famous residents, was mayor of the city, helped develop it, and is buried there.

He endowed the (now defunct) Barnum Museum of Natural History at Tufts University in Massachusetts, but as numismatic writer Arlie Slabaugh Jr. put it, "his greatest monument is the circus.

The growing market for such pieces led to many commemorative coin proposals in Congress, to mark anniversaries and benefit (it was hoped) worthy causes, including some of purely local significance.

[7] A bill for a Bridgeport Centennial half dollar was introduced into the United States Senate by Augustine Lonergan of Connecticut on March 10, 1936.

Other issues had been entirely bought up by single dealers, and some low-mintage varieties of commemorative coins were selling at high prices.

[15] On April 28, Schuyler Merritt of Connecticut brought the bill to the House floor, asking that it be passed with the recommended amendment, and it was, without any discussion or dissent.

On May 4, Adams moved that the Senate agree to the House amendment, which it did;[17] the bill became law, authorizing not fewer than 25,000 half dollars, with the signature of President Franklin D. Roosevelt on May 15, 1936.

[3] On June 10, 1936, Bridgeport mayor Jasper McLevy wrote to Director of the United States Mint Nellie Tayloe Ross, informing her that Henry Kreis, designer of the Connecticut Tercentenary half dollar, had been hired to sculpt the Bridgeport coin, and enclosing sketches of the proposed design.

[19] The commission was charged by a 1921 executive order by President Warren G. Harding with rendering advisory opinions on public artworks, including coins.

[21] The models were converted to coin-sized hubs by the Medallic Art Company of New York in time for coinage to begin in September.

[22] The obverse of the Bridgeport half dollar depicts the bust of P. T. Barnum, a subject that has absorbed much of the commentary on the coin's design.

[24] Dealer B. Max Mehl, in his 1937 work on commemoratives, suggested purchasers of the coin were "suckers", and wrote, "we think that Barnum's likeness, in view of his famous remark, is certainly most appropriate".

David Bowers describes Kreis's eagle as modernistic and noted its resemblance to the one the sculptor had created for the Connecticut half dollar.

[28] He described the piece as having "P. T. Barnum in large, thoughtful profile and a thrusting eagle of conceptual, metallic style", and praised the lettering, finding the placement of the patriotic mottos on the reverse done "not inartistically".

[28] Vermeule suggested that Kreis was unable to find a suitable Bridgeport-related theme for the reverse, and instead turned "to a new interpretation of elements, such as the eagle, used in the coins of the regular issue.

A coin honoring P. T. Barnum could have featured a lion, an elephant, or a performing bear on the reverse, but this product of the civic enterprise of Bridgeport gains great merit for showing an exciting new form of the national bird".

[28] In September 1936, a total of 25,015 Bridgeport half dollars were struck at the Philadelphia Mint with 15 pieces reserved for inspection and testing the following year by the annual Assay Commission.

[31][32] Several thousand pieces remained unsold, and transferred by the centennial organizers to the Bridgeport Community Chest, which sold them wholesale to coin dealers at a slight advance on face value.