Dowd was employed by several law firms in the Washington, D.C. area for his expertise in defending clients accused of white-collar crimes.

During the summers, Dowd worked at Sankaty Head Golf Club on Nantucket Island where he became acquainted with trial attorney Edward Bennett Williams.

[5] Working for the Department of Justice, Dowd was a trial attorney for the tax division and later as a chief of an Organized Crime Strike Force from 1974 to 1978.

[2] His early career at the Department of Justice involved working on the tax evasion case of mobster Meyer Lansky, the prosecution of Small Business Administration bribery cases in Virginia, and internal investigations involving financial corruption by Federal Bureau of Investigation (FBI) officials.

Dowd stated in a 1993 interview on Frontline that the investigation revealed, "Hoover had taken, at taxpayers' expense, goods and services provided by employees of the FBI.

[8]: 263  Dowd questioned Flood's former aide, Steve Elko, who accused Flood on a number of federal contracts in exchange for cash kickbacks and also mentioned Pennsylvanian Congressman Joshua Eilberg's law firm handling the contract negotiations for a federal grant to Hahnemann University Hospital.

[5][6] In April 1979, The Wall Street Journal reporter Jim Drinkhall, wrote an article accusing federal prosecutors Dowd and William M. Kramer of developing and implementing an unethical plan to force a convicted felon, Samuel Ray Calabrese, to cooperate with the government against other organized crime figures.

[11][13] Following his departure at the Department of Justice in 1978, Dowd was hired by the law firm Whitman & Ransom as a partner in their Washington, D.C. office to represent defendants accused of white-collar crimes.

[17][18] Reckmeyer petitioned to vacate his sentence making the accusation that Dowd had requested and knowingly accepted illegally sourced funds as fees for his services.

[24]: 355  In the film, The Informant!, which is based on the lysine price-fixing conspiracy, Dowd was portrayed by stand-up comedian Bob Zany.

[31] Dowd defended hedge fund manager Raj Rajaratnam, founder of the Galleon Group, in his insider trading case.

[36] Dowd recommended to President Trump that attorney Ty Cobb be added to his legal team to manage matters with the special counsel.

[38][39] It was reported Dowd had drafted the tweet that stated Trump had to fire General Flynn after he lied to the vice president and the FBI.

Legal commentators quickly raised the question of whether, in fact, Trump knew Flynn lied to the FBI when he fired him in February 2017.

Dowd emailed the House Intelligence Committee that they would not comply with an October 7 deadline to hand over documents concerning an impeachment inquiry of President Trump.

The two men had previously peddled information to President Trump's attorney, Rudy Giuliani, about Ukrainian corruption involving Joe Biden and Hillary Clinton.

[45] Dowd was the Special Counsel to the Commissioner of Baseball that led to the banning of MLB player and manager Pete Rose for the Cincinnati Reds.

In his role as Special Counsel to the Commissioners, Peter Ueberroth and subsequently A. Bartlett Giamatti, he submitted a 225-page report in May 1989, which detailed Rose's betting on baseball games in the 1980s.

[53] At the request of Baseball Commissioner Fay Vincent, Dowd was assigned to compile a report on New York Yankees owner George Steinbrenner's $40,000 payment to Howard Spira to dig up dirt on outfielder Dave Winfield in 1990.

[55] The suit where Bowman and McCarthy sought $30,000 in damages from Dowd was thrown out in court in early 1991 by District Judge Robert W.