A Democrat serving most of the Near North Side, he represented such affluent constituencies as the Gold Coast and Streeterville as well as such poor areas as Cabrini–Green and Goose Island.

A corrupt and mob-linked yet popular and effective alderman, Crowe kept his affiliation with the machine in a changing climate and was able to maintain and entrench his power within the 42nd ward as the decades wore on.

He received preliminary aviation schooling at Cornell University and more detailed training at Kelly Field in San Antonio, reaching the rank of Second Lieutenant in 1918.

[15] He did run in 1916, winning the Democratic primary against John Prendergast[16] but falling in the general election to Republican candidate Earl J. Walker,[17] who was aided in part by society women who learned oratory for the purpose.

[18] Then, as in 1919, his family history was used against him, although the women also asserted that he had been floor manager for a hotel employees' ball that had turned into a drunken orgy.

At that time he was serving as an Army aviator and had been injured the previous autumn while distributing propaganda for war bonds when his plane crashed and he fell 800 feet (240 m),[5] in large part winning on a sympathy vote[12] and defeating Republican incumbent Robert Hall McCormick (not to be confused with Robert R. McCormick, who had been Republican alderman of the same ward from 1904 to 1906[21]),[22] who was further perceived to have a very poor attendance record at the Council,[23] 8,735 votes to 6,287.

He also proposed to electrify all of the railway terminals in the city to reduce smoke and noise, and supported giving jobs to veterans returning from France.

[25] In his first year as alderman, Crowe was a member of the Judiciary, Streets and Alleys, and Building and City Hall committees of the Council.

[27][21] In the aldermanic election that year the Municipal Voters' League would reverse its position on him, endorsing him as "[having] courage and show[ing] capacity for further good council service".

[28] On May 23, 1922, he was one of seven aldermen to call a special meeting of the Council to consider adding 1,000 patrolmen to the police force, which was ultimately approved.

[31] Despite coming from a greatly anti-Prohibition area, in 1923 he voted against a resolution proposed by fellow Democratic alderman John Coughlin of the 1st ward that New York Governor Al Smith be commended for signing a prohibition enforcement repeal act and that Illinois to do the same.

He claimed that the vote was because he didn't have enough time to consider the resolution, although prominent wet and Cook County Board of Commissioners President Anton Cermak insisted it was because Crowe wasn't allowed to introduce it, and criticized him and 43rd ward alderman Arthur F. Albert for voting against the resolution when their respective U.S. Representative Frederick A. Britten was leading the fight against the Volstead Act in Congress.

[36] Despite such mob links, he endorsed, and his ward voted for, incumbent anti-mob and Prohibition-enforcing mayor William Emmett Dever in the 1927 election.

In particular, the reform-minded Chicago Tribune, whose headquarters were located within the ward, and his old enemy the Municipal Voters' League, despite its 1921 and 1923 reviews, continued to endorse his opponents throughout the decade.

The campaign was active and violent, involving such violence as fistfights and shootings, and Crowe's precinct captain Charles S. Brown would be found dead in September.

[44][45] On June 2, 1929, Crowe was involved in an automobile accident in Lake Forest in which his vehicle was crowded into a ditch and he was thrown through the roof of the car[46] and pinned in the wreckage before being saved by a passerby as it began to catch fire, suffering a concussion and being rendered unconscious for six hours.

[48] The onset of the Great Depression initially spelled problems for Crowe, with seven rivals vying for his seat in 1931, at least two of whom – hoteliers Thomas Daniel Collins and Charles F. Henry – receiving significant support.

"[c][10] By 1960, the composition of the 42nd ward was changing, with an influx of recent immigrants from Mexico, Puerto Rico, and the Philippines, and a third of the voters being African-American.

His good friend and longtime ward committeeman William J. Connors was known as "Old Reliable" due to his obedience to the wishes of the machine.

[55] In 1928 as an alternative to the delayed project of a Downtown airport that would eventually become Meigs Field he proposed an airstrip on the site of then disused Oak Street Beach,[56] which would continue into 1929.

He moved to the Gold Coast sometime in the 1920s, living by 1929 at 65 East Bellevue Place with his mother, brothers Stephen A. and Orpheus E., aunt Frances C. Ryan, a servant, and a lodger.

[63] In 1951 a safe weighing several hundred pounds and containing no cash but miscellaneous insurance policies, warranty deeds, and a $1,000 cashier's check made out to the Chicago Title and Trust company for use in a realty transaction, was stolen from his real-estate office.