Desmond is the president of Cobblepot Amalgamated which has major construction and shipping subsidiaries. He inherited the position after the disappearance of Osmund Cobblepot, his uncle.

The Depression has put Desmond in a desperate position, with pressure to merge his shipping company with the Wayne's and slow down in construction orders both putting on the squeeze. He has become quick to anger and erratic of late because of the pressure. His big hope lies in the imminent opening of Cobblepot Towers, in Old Gotham, a luxury business and residential high rise.

While the towers are being built, Desmond has avoided the ancestral (and frankly decrepit) Cobblepot House in the East End, and lives in a fashionable apartment in Gotham Tower Apartments in the Diamond District.

Declan O'Toole of The Wound Ravens Gang masterminded a scheme to arrange loans to Desmond, using most of the family property as collateral. Desmond expected to use major influx of cash from the opening of Cobblepot Towers to pay off the loans. So, O'Toole destroyed the North Tower of the complex with a bomb. Desmond was emotionally shattered, and despite O'Toole's arrest, Desmond remains in bad condition.

Desmond was “protectively kidnapped” by Team C of the Restoration Project on May 28,1934. The team then killed the escaped Declan O'Toole, in his guise as “The Flaming Death” who had come to kill Cobblepot.