After being caught in 1957 as he attended a national Mafia meeting that was raided by State Police in Apalachin, New York, Montana's criminal ties became known and the popular public figure was reduced to a "former gang boss."

Born in Montedoro, Sicily on July 1, 1893, Giovanni Montana came to Buffalo at the age of thirteen in June 1907 and quickly began to show his entrepreneurial business talents.

With his brothers Salvatore, Angelo, Peter and Joseph, the 17-year-old John Charles Montana first pushed a popcorn cart through Buffalo's Little Italy at a time when Italians lived in a high density area on the Lower West Side and downtown.

On the Council, he was the Chairman of the Housing and Slum Clearance Committee, which gave his Mafia associates a direct influence over where people lived and what reconstruction efforts would be made.

Many major changes came to the Queen City during his time as a political leader, and John Montana made sure that his hidden partnerships never came to light while still placing people in positions to reap the benefits of the construction and transportation boom.

During his term on the Council, Montana witnessed many changes in Buffalo, including the aforementioned opening of the NY Central Terminal, the Peace Bridge, the airport, and the New City Hall building.

To come along to Chicago to mingle with the nation's top Mafiosi, he invited his close friend and advisor John Montana, the #3 man in Buffalo's Mafia behind Stefano Magaddino and his brother Antonio.

Bonanno, who was Stefano Magaddino's younger cousin, went to the national summit by train from New York with a contingent of men including Lucky Luciano and Salvatore Maranzano.

In September 1932, The Association of Taxicab Owners and Operators of Buffalo, NY, asked the Common Council to combat the new taxi companies and make fares standard across the board.

With over three hundred drivers in the union, Business Agent Joe Gerrity of Teamsters Local 153 had a meeting in the back of a saloon and his riders decided to go on strike with a vote of 184-9.

Montana was chosen as an alternate delegate from New York and mingled with top politicians as they endorsed Alf M. Landon and Frank Knox to run against FDR and his Vice President.

From the 41st District of the House, made up heavily of the Italian West Side, Republican Party leaders handpicked J. Francis Harter, an Amherst Attorney, as their candidate.

When many people opposed because Harter lived outside the 41st District – outside of the City of Buffalo all together – John Montana used it as his blessing to create a splinter in the Erie County Republican Party and lead a dissident faction that supported his candidacy as a representative to the U.S. House.

"In these turbulent times when other nations are depriving their citizens of a voice of the affairs of government, it should be the duty of political leaders in America to show the way in affirming faith in Democracy."

While these were all important rules in the State's history, nearly 25 years later authorities would have to release mob boss Stefano Magaddino after he was implicated in over 1,000 hours of recorded footage that was thrown out of trial because a judge never approved the wiretaps before they were installed.

But while they needed lower echelon racketeers and brutal hoods to carry out the day-to-day activities of the Mafia, John Montana had a high place in society to ensure policies and opportunities for the Family.

When prohibition was ended in the early 1930s, Montana moved in and legally purchased breweries to supply the now-legal alcohol industry still dominated by the Mafia and their distribution connections in German, Polish, Irish, and African American neighborhoods in the region.

While still catering to the German market that the Dotterwyck Beverage Company allegedly made illegal alcohol for during prohibition, Montana's Empire State Brewery sold Old Dominion Ale and Old Munich Beer.

As secretary-treasurer of the company, Charles Montana, John's nephew, signed the papers to fold the business and he held a powerful position within Magaddino's Mafia Family.

Montana's business success would bring tremendous legit revenue and resources into the Mafia's sphere of influence, and they would also provide secure outlets to turn illegal cash into legal income through money laundering.

Whenever there was a dispute in zoning, Montana's decisions would carry a lot of weight – and his associates had a direct line into an important and overly managed sector of Buffalo's city government.

With pleas to the mayor for help, the Independent Taxicab Association of Buffalo, NY claimed that Montana was given unfair contracts during World War II to operate exclusively across the city – violating the fair monopoly laws of the day.

Van Dyke Taxi and Transfer was the only company allowed to move travelers to the Buffalo Central Terminal on the East Side and was able to drive all over and purchase gas when rations forces others out of business; police were even aggressively ticketing or impounding any other taxicabs nearby.

The president of the independent cab association, Thomas Caverly, created a publicity battle against Montana through the newspapers: "I fail to see why the City of Buffalo should be paying the salaries of its police department to assist the New York Central and to protect their contract with the Van Dyke Taxi and Transfer Company."

Toastmaster, attorney Michael Catalano (later to be elected as a Supreme Court Justice of the State of NY) had good words to say about Montana as did Albert S. Scialfo, head of the Italian-American Societies that sponsored the event.

Magaddino, however, lobbied to have the meeting held in Upstate New York, at the home of his old Castellammarese soldier-turned-boss of a smaller Northern Pennsylvania Mafia Family Joe Barbara.

John Montana in a nicely attired suit was also picked up by New York State Police straddling a barbed-wire fence – the first time in his illustrious career he was ever publicly linked to the Mafia.

Senator Bobby Kennedy, the President's brother, asked about Montana's association to Paul Palmieri, an important Castellammarese gangster from Niagara Falls who moved to New Jersey.

On November 29, 1960, however, the United States Court of Appeals for the Second Circuit decided that none of the attendees really committed a crime by meeting, and they were all freed from jail or bail, including the 66-year-old Montana who now lived at 340 Starin Avenue in North Buffalo.

His power in the Mafia dwindled quickly after being caught on a barbed-wire fence – he even asked to be demoted in his later years as he didn't want the responsibility or police heat that's generally attributed to mob bosses.