His arrest taking place shortly after midnight, he successfully escaped custody twice before finally being returned in the prison attached to the Yorkville Court at the end of the day.
It was during one of these escapes that he visited the office of District Attorney Charles S. Whitman in which he claimed he was not being given a "square deal" by police and asked for protection.
On June 17, 1914, Madden was arrested for complicity in the mugging of a Mrs. Artha Ingram, a collector for the Phips Model Tenements, near her office at East 31st Street.
Madden was able to escape the room by opening up the window slightly, shinnying up a water pipe and sliding over the top of the sash and the points of the spikes.
It was at that moment that Morris W. Reedy, an officer for the Department of Corrections and captain of its steamship the Josephine Whitney, had spotted Madden leaving the building.
On September 10, he and Ryan were handcuffed together and marched with ten other prisoners from The Tombs and across the Bridge of Sighs to the nearby Criminal Courts Building.
However, authorities believed Madden had slipped away down one of the two unguarded stairways while the prisoners were marched through the second floor of the Criminal Courts Building.