As an attorney, Coakley took part in numerous badger game extortion schemes and was disbarred in 1922 for deceit, malpractice, and gross misconduct.

[3] He was impeached and removed from office in 1941 for using his position and influence to secure pardons in exchange for financial gain.

In 1892, Coakley left the Herald to attend Boston University Law School and launch his first campaign for public office.

He was unseated in 1896 and moved across the Charles River to Boston, where he worked on the reelection campaign of U.S. Representative John F. Fitzgerald.

[12] In 1914, Coakley was sued by the widower of one of his clients, to recover the full amount of the $15,952 awarded to her in a suit against the Boston Elevated Railway.

[2] In 1913, Elizabeth "Toodles" Ryan, a cigarette girl at an illegal gambling establishment, hired Coakley to represent her in lawsuit against her employer, Henry Mansfield, who she said had reneged on his promise to marry her.

[2][19] Curley announced he would deliver a series a public lectures, including one entitled "Great Lovers in History: From Cleopatra to Toodles.

The incident was now a matter of official court record and made front-page headlines, which started the decline of Fitzgerald's political career.

Coakley got the investigation dropped by having the case transferred to District Attorney Joseph Pelletier, whom he had helped elect.

On December 16, 1918, the council of the Boston Bar Association voted to investigate the conduct of Pelletier, Coakley, and Francis Carroll in connection with a case involving Emerson Motors Company.

[21] Pursuant to that investigation, Michael J. Hayes stole papers from Coakley's office and turned them over to Godfrey Lowell Cabot of the Watch and Ward Society.

On November 18, 1920, a grand jury indicted on Hayes, Cabot, and three other men on charges of conspiracy to steal Coakley's papers and larceny of property.

[22][24] On September 29, 1921, the Boston Bar Association filed disbarment petitions against Coakley, Daniel V. McIssac, and former Middlesex District Attorney William J. Corcoran, along with a recommendation that Pelletier be removed from office, alleging that all four were guilty of deceit, malpractice, and gross misconduct.

The allegations included:[25] On April 17, 1922, Coakley walked out of a hearing and dropped his defense, stating that he felt he could not get an impartial trial.

[27] On April 21, the Massachusetts Supreme Judicial Court found that Coakley was guilty of deceit, malpractice, and gross misconduct.

[33] On November 14, 1934, a jury awarded $77,433.33 to Francis D. Reardon of Emerson & Co. for failure to pay a $50,000 note owed by Coakley and his son-in-law, Charles L. Murdock, to the company's deceased president, Bartholomew Crowley.

[39] He ran a third time in 1933, but dropped out of the race, stating that he feared his "candidacy was likely to result in the election of an enemy of the plain people.

[3] During his tenure on the Council, Coakley acted as a prosecuting officer in many removal proceedings brought by Curley against state officials.

Through his alliance with Governor Curley, Coakley was able to secure 2,000 patronage jobs for men from his district on the Quabbin Reservoir project.

[5] In 1938, Coakley wrote the petition for a pardon of Raymond Patriarca, a young mobster who later became the boss of New England organized crime.

[43] On June 9, 1941, a special House committee found that Coakley had used his position and influence to secure pardons for Patriarca, Maurice Limon, and Frank W. Porter in exchange for financial gain and recommended his impeachment.

The Senate voted 28 to 10 to remove Coakley from office and 23 to 15 to bar him for life from holding a place of "profit or honor or trust" in the Commonwealth.