June 02, 2015

Consider Sal DiMasi, Dianne Wilkerson, or go back to the MBM Scandal of the Seventies. All amateur operations, really. For real corruption, you have to read about Bostonian Dan Coakley, in the new book by Patrick S. Halley: Dapper Dan: America’s Most Corrupt Politician.

Quite a few Bostonians know the story of how James Michael Curley forced Mayor John “Honey Fitz” Fitzgerald out of the Boston mayor’s race in 1913, but fewer know that it was Coakley who helped engineer the mayor’s exit. Fitzgerald and Coakley had been at loggerheads but in hopes of currying favor with Attorney Coakley the mayor had sent him a potential legal client. The client’s name was Elizabeth Ryan, but to the mesmerized patrons of the roadside inn and illegal gambling parlor where she plied her trade, she was known as Toodles. It didn’t take Coakley long to extract from her that her professional duties extended beyond hostessing and that one of her  most ardent visitors was none other than the very married and very Irish Catholic John Fitzgerald. Despite Fitzgerald’s efforts to win him over, Coakley remained bitter at him over past political battles. Coakley quickly betrayed Fitz’s secret to a pol with more potential to aid Coakley: James Michael Curley. The conspirators had a letter delivered to the home the mayor shared with his wife and daughter, Rose Fitzgerald. The women were waiting for him when he returned home; it did not go well. Fitzgerald had to confront the fact that things would likely not improve when Curley announced a series of three public lectures, including one entitled “Great Lovers in History: from Cleopatra to Toodles.” Fitzgerald dropped out soon afterwards. 

As an attorney, Coakley’s services were sought by many a miscreant, especially those whose problems were related to political corruption. This was fitting, since Coakley had frequently been the one to get them into a mess in the first place. He had two very successful trial techniques. His first, and favorite, was to bribe the district attorney. On occasion he would have to try a case against some incorruptible type and he was forced to his second approach: bribe the jury. Coakley was eventually disbarred, a misfortune that gnawed at him for years. Part of his plan to regain his law license involved a return to elective office, so he won a seat on the Governor’s Council – the body that has the power to confirm or decline the governor’s judicial appointments!

Among Coakley’s other achievements, he got three different district attorney’s disbarred or impeached for selling get out of jail cards. With Curley’s assistance, Coakley blackmailed Hollywood moguls out of what would be millions in today’s money over a visit to a Woburn brothel. He represented the infamous investment fraud Charles Ponzi, inventor of the Ponzi scheme – Ponzi wound up broke and in jail, the investors lost their money, and Coakley got rich. He arranged a pardon for notorious mobster Raymond Patriarca – a move that finally led to Coakley being impeached from the Council.

That’s just a sampling. Dapper Dan really was America’s most corrupt politician; and he was Boston’s own.

Patrick S. Halley, Dan Coakley

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