What I Am Reading: "Dapper Dan: America's Most Corrupt Politician" by Patrick S. Halley
I didn’t have high hopes for this book. Judging a book by its cover isn’t the same as judging it by its publisher, and this book appears to be self-published, and is definitely print-to-order. There is no index or table of contents, and paragraphs throughout the book are separated by line breaks, except for the random occasions when they are not. There are also a handful of typographic and spelling errors, and occasional lack of clarity in dating events. I found this self-publication origin slightly surprising because the author is a former advance man for Hillary Clinton and has had a career in Massachusetts politics and government, thus presumably has a pedigree and connections. I found the origin even more surprised as I got into it, because the book’s content is in fact quite good.
The book is about Daniel H. Coakley, a political figure in Massachusetts from the 1890s to the 1940s. His main biographic items are that he was the first elected official to be impeached in Massachusetts in over a century, and that he was at an earlier point the lawyer to the legendarily flamboyant and corrupt Mayor of Boston James M. Curley. From these two data points, I had expected that it was the case of some corrupt machine flunky being given the business, but in fact Coakley was a major mover-and-shaker during his half-century in politics.
Coakley, born in 1865, got his start as a labor agitator in Cambridge’s streetcar business, then transitioned into sports journalism. By the early 1890s, he transitioned into politics with a run for a seat in a multi-member State Representative district in Cambridge. He and his brother Timothy, who ran several times for State Senate across the river in Boston, built up their own small machine between them, and their clever maneuvering and dogged campaigning was good enough to send Dan to the House twice, though Timothy was never successful in reaching the Senate.
After being bounced from the House in 1896, Dan worked at a new legal career, reading law under his brother. He served as defense counsel to many local politicians accused of various corruption offenses, trading on his political connections and never afraid to facilitate money changing hands if it won the case. His insider status was threatened by his brother’s quixotic crusades against the Democratic establishment; but this dynamic provided their big break when Tim managed the campaign of a no-hope independent candidate for Suffolk County District Attorney in 1905 who actually won. Suddenly, the Coakley law firm had connections on the prosecutorial side of things.
Tim was out of the way before too long, dead of tuberculosis; and the District Attorney, John B. Moran, was as well, dying in his second term in 1909. However, Dan had used his pull to raise up Joseph Pelletier, who was elected in 1909. This was the start of Coakley’s big racket. Through the use of blackmail, set-ups, and selective prosecution, Pelletier dismissed the (sometimes fraudulent) charges of marks who had, under Pelletier’s stern advice, retained Coakley as their attorney. In return, Pelletier made a portion of the enormous fees that Coakley charged for this service. Coakley became a very rich man and a pillar of the Boston Irish elite, his nickname “Dapper Dan” coming from his sartorial splendor.
He managed to keep this arrangement going for over a decade, even spreading his tendrils into Middlesex County through their own clean-cut and WASPish Republican DA. During this time, Coakley was one of Boston’s big movers and shakers, helping bring down Mayor John “Honey Fitz” Fitzgerald, JFK’s grandfather. The mayor, for some reason sent Coakley, with whom he was at odds, the business of the young underground casino waitress he was seeing, Elizabeth “Toodles” Ryan- perhaps as a peace offering. The Toodles affair is famous in Boston and Kennedy lore; but Toodles doesn’t appear to have any images online, an injustice that I have rectified below. Anyway, Coakley put word of the affair before the right individuals, and the result was that rising politician James Michael Curley was elected Mayor for the first time after blackmailing Honey Fitz out of the race. Though Curley scrapped with Coakley at first over the latter’s service on the board of the Parks Department (and his patronage from this, which Curley wanted to take over), they made up enough for Curley to retain Coakley as his attorney during an investigation by the city’s Finance Commission, which Coakley quashed through having it referred to the compliant Pelletier.
Elizabeth “Toodles” Ryan, the cigarette girl at the center of the secret scandal that let Curley blackmail Honey Fitz (picture from The Marion Star. Marion, Ohio. June 30th, 1915. p.3). “She was twenty three years old and the very picture of feminine beauty. A former model with long blonde hair, sparking blue eyes and a figure that would stop traffic, she … exuded a sexual magnetism that served her well in her job as a hostess at a roadside inn where her duties included including customers to leave the dining room and join her upstairs in the illegal casino.” (Dapper Dan, p. 105).
Bribes were paid, juries were fixed, and the high life was lived until trouble arrived in 1920. Coakley made an enemy in the form of Godfrey Lowell Cabot, the richest man in Boston and the head of an anti-profanity society. Cabot pushed the Boston Bar Association to investigate Coakley, though Coakley outmaneuvered him when Cabot overreached and had Coakley’s office illegally bugged. Coakley did not get Cabot for this, but the bugging did put Cabot’s group onto Pelletier’s trail. While Coakley was busy defending the eponymous creator of the Ponzi scheme that year (arranging things so that he faced lesser federal charges), the Attorney General and the Bar Association investigated Coakley, Pelletier, and Nathan A. Tufts, the above-mentioned Middlesex County DA. Coakley’s history of extortion and malfeasance came to light in the trials that took place through 1921, and he was disbarred in 1922. Neither he nor Pelletier offered anything in their own defense, hoping for unreceived mercy from the court.
The disbarment was a source of great anguish for the rest of Coakley’s life, and he maintained the long-term goal of being re-instated to the Massachusetts bar. In the meantime, however, he turned to politics. Pelletier did as well, but took ill and died during a campaign for Mayor in 1924, the year before the election. Mayor Curley’s mocking criticism of Pelletier turned Coakley against him. Curley couldn’t run again in 1925, but Coakley ran against his handpicked and unprepossessing candidate, fire commissioner Theodore Glynn. Coakley achieved a distant but respectable fourth place with 11% of the vote as Glynn lost 23% to 35% for the winner, Malcolm Nichols. When Curley returned in 1929, Coakley again took to the campaign trail, regularly renting radio time to criticize, mock, and bait Curley at great length. This did not slow his momentum, and Curley steamrolled Coakley and his other opposition.
The two had their final clash by proxy in 1930, when they were supporting different candidates for the Democratic nomination for Governor. Curley wanted to run himself in 1932, and thus put up the increasingly frail Honey Fitz as a placeholder who would lose to the Republican and keep the Democratic nomination open. He continued to push for Fitzgerald even after the latter dropped out of the race, afraid perhaps of Coakley’s voluminous broadcasted criticism and deep pockets. Coakley, meanwhile, supported Joseph B. Ely of Westfield, formerly the District Attorney from the Western District of the state. Though Curley’s farcical campaign for a candidate who had dropped out wasn’t making any headway against Ely’s argument that he could pick up Republican votes in Western Mass, Curley kept the pressure on. On election eve, he was early for a radio broadcast, and he became so incensed at the speech of Coakley’s pro-Ely speaker in the slot before him that he stormed into the recording booth and tried to assault the man. Coakley’s son Gael tried to hold him off, and received a Mayoral knee to his groin for his troubles.
Despite this showing, Coakley’s candidate was victorious in the primary and, despite the Republican invocation of Coakley’s name as a campaign-trail boogeyman, in the general. Coakley spent the first term as just an advisor, but soon wanted to get back into the game more directly. He ran for the only safely Democratic seat on the Governor’s Council in 1932 (located in South Boston), and won handily. The Council was more powerful in those days, and in addition to judicial and parole board appointments, controlled some aspects of state spending. Despite his return to respectability, he was unable to convince the Bar Association to re-instate him, and Coakley, approaching his late 60s, suffered ill health from the stress of this critical final argument of his failed redemption.
Ely was replaced by none other than James M. Curley as Governor in 1934, and he and Coakley buried the hatchet to their mutual benefit. The elections had upped the Democratic membership to three, and Curley promptly offered lifetime patronage posts to two of its Republicans, allowing him to appoint two Democrats to the vacancies and claim the majority. Curley and Coakley cooperated on patronage (including that of the “woodpeckers” clearing the Quabbin Reservoir land) and Coakley soon got into his last bit of trouble, steering and accepting bribes in return for pardons, with the Council’s control of the pardon board.
This continued for a few terms, through Curley’s tenure and that of his Democratic successor, Charles F. Hurley. Every candidate for statewide office took Coakley’s name in vain, though they were careful to do so quietly lest they incur his wrath. In the end, the pardon that attracted the attention that brought Coakley down was of a surprisingly familiar name: Raymond L. S. Patriarca, who went on to be a famous Providence mob boss. In this era, though he was part of a larger organized crime network, Patriarca was still just a burglar, arrested and sentenced in 1938 but then pardoned by Hurley in his lame-duck period, at Coakley’s special arrangement. The uproar over this led to an investigation by the Pardon and Parole Commission, and eventually by the legislature. In the new term, Coakley was the subject of a scathing report (such a bombshell that they released an interim report half-way through their investigation), and a legislative inquiry that recommended his impeachment in early 1941, the first such since the 1820s.
Coakley was sanguine about his 144-74 impeachment in the House, and kept his powder dry for the Senate trial (not that he had a choice, since he was barred from the House floor). His attorneys pulled out all their saccharine stops, though Coakley was baited occasionally into the “high-octane histrionics” that made up his courtroom persona and his Governor’s Council meetings, both delightfully excerpted. The impeachment managers focused on three of the main parole cases, including Patriarca’s, and in the end Coakley was found guilty on nine of fourteen counts. The Senate voted 28 to 10 to remove him from office, and 23 to 15 to bar him from seeking office in the future. At that point, the book swiftly wraps up, noting that Coakley never served a day in jail, and died in 1952. He mostly spent his remaining time in his Buzzard’s Bay mansion or suing people over slights for the opportunity to represent himself in court as his own attorney, having never gotten over his disbarment. He entertained the idea of running for Senate in 1942 (and OurCampaigns says he was actually on the ballot), and also drafted an autobiography named “The Sparkling Past” that never saw the light of day, much to the relief of many contemporary politicos (but to the historian’s detriment).
The proximate cause for reading this book was for information on Roland D. Sawyer, a State Representative from Ware who was a main figure in Coakley’s impeachment (and also played a role during his long tenure in the Quabbin Reservoir creation, a different story entirely). Sawyer is one of my prospective writing topics; “obscure but important” is my watchword and that applies to both him and Coakley. I am trying to ramp up in general my reading of anything available on New England politics in the years between the wars, not an extensive list. To that end, this book convinced me to pursue more raucous scandal through a James M. Curley biography, a topic I had shied away from in the past as too Boston-centric.
As noted, I was skeptical of the book’s origins, but I found the content to be highly enjoyable and readable. I think that the book is handicapped by its non-commercial publication. Halley clearly did a lot of research, and the myriad of newspaper articles are cited in the back of the book. I think that the subtitle of “America’s Most Corrupt Politician” is an over-sell, but the strong Massachusetts angle makes this recommended #MApoli reading from me.