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About me

Boston Criminal Defense lawyer, Brad Bailey, a Massachusetts native white collar, sex, drugs & violent crimes (including homicide) attorney, graduated cum laude from Harvard College in 1980. He received his J.D. in 1983 from the University of Virginia, one of America’s premier (top 10) law schools. He began his legal career working for the New York County (Manhattan) D.A. as an Assistant District Attorney in the Nation’s largest and busiest D.A.’s Office. While there, he prosecuted serious street level felonies, including armed robberies, burglaries, attempted murders, felony weapons charges and felonious assaults. He achieved a conviction rate of 94% and handled thousands of cases during his tenure. From there, he returned home to Massachusetts and joined the Middlesex County D.A.’s Office, where he continued his career as an Assistant District Attorney. A senior Trial Attorney assigned to both the Cambridge and Lowell regions, Brad prosecuted some of the most serious cases in the D.A.’s Office including murders, rapes, attempted murders, armed robberies, child sexual assaults, and cocaine and heroin trafficking. In a mere 22 months, he tried 26 felony cases to verdict in the Superior Court (an Office record at the time). Losing only twice, Brad achieved an overall conviction rate of over 92%. Brad moved on from the Middlesex D.A.’s Office to the prestigious United States Attorney’s Office for the District of Massachusetts, where he served as an Assistant U.S. Attorney in Boston, first with the Organized Crime Strike Force and later with the Drug Task Force (OCDEFT). While in the Strike Force, Brad directly participated in the prosecution of a number of members and factions of the Patriaca Crime Family of La Cosa Nostra (LCN) including reputed Underboss Charles Quintina, Capos Biagio DiGiacomo and Sonny-Boy Rizzo, and Soldiers Spucky Spagnuolo, Vincent “Dee Dee” Giachinni, Pryce Quintana and Freddy Chiampa. He also authored and oversaw numerous court authorized wire-taps. When in the Drug Task Force, Brad prosecuted numerous local, regional, national and international drug conspiracies, principally involving Colombian and Dominican distribution cells and Syrian and Lebanese drug traffickers. Also the co-lead prosecutor in a case involving the then largest marijuana smuggling ring in New England history, Brad never lost a trial as a federal prosecutor and achieved the Office’s highest ranking: “Outstanding Prosecutor.”


Brad went on to serve as Sheriff of Middlesex County for two years from 1995-1996. In that role, he was responsible for the daily care, housing and transportation of close to 2,000 inmates and detainees at correctional facilities in Cambridge, Framingham and Billerica and oversaw a staff of more than 750 county employees. He was also responsible for courthouse security and the service of civil process throughout Middlesex County. While Sheriff, he was honored as one of the 1996 “Ten Outstanding Young Leaders” by the Greater Boston Jaycees.



Brad returned to the private sector in 1998 and has concentrated since then in high-end state and federal criminal defense involving all types of crimes and charges.  He has defended some of the highest profile cases in Massachusetts, as well as throughout the New England Region and elsewhere in the U.S. He routinely defends clients in cases alleging: murder, rape, robbery, home invasion, larceny, theft/embezzlement, white collar offenses, fraud, public corruption, narcotics distribution/trafficking, arson, racketeering, child sexual assault, child pornography, felony assault, DUI, and all other types of federal crimes and charges.



A longtime member of the select CJA panel (approved by the U.S. District Court to represent indigent clients in federal court) as well as a member of the select CPCS murder list (for indigent murder clients), Brad is admitted to practice before the United States Court of Appeals for the 1st Circuit, and also licensed full-time to practice in the District of Massachusetts (federal), the Southern and Eastern Districts of New York (federal), as well as in all state courts, at all levels, in both Massachusetts and New York.  Despite being based in Boston, because of his national reputation, in addition to handling numerous cases in New Hampshire and Connecticut on a pro hac vice basis, Brad has also been admitted pro hac vice in federal or state courts in ME, CA, AZ, MD, WI, VA and NJ and has extensive appellate experience having filed and/or argued cases in the Federal 1st Circuit Court of Appeals, Supreme Judicial Court, and Massachusetts Court of Appeals. He also appears before regulatory agencies including the SEC and the NASD, as well.


A regular guest analyst on local radio and television stations, Brad now provides exclusive television commentary for FOX television’s Boston affiliate regarding cases of local, regional, and national importance.  A repeat Massachusetts Super Lawyer, including this year (2014), Brad has also been recognized as a New England Super Lawyer.  He received top ratings from Martindale Hubbell (“AV”) and AVVO (“Superb”) and was voted a National Top 100 Trial Lawyer.



A former Harvard Football Player, with four adult children, all of whom were accomplished high school athletes, three of whom also participated in varsity sports at the inter-collegiate level, Brad is well-versed in MIAA rules and regulations, as well as governing codes of discipline of high school and collegiate athletics. He remains active in his local community.


Photos and videos

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Practice areas


  1. Sex Crime: 20%
  2. Federal Crime: 20%
  3. Violent Crime: 20%
  4. White Collar Crime: 20%
  5. Criminal Defense: 20%
    13 years



Free consultation (30 minutes)

Payment types:

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Attorney endorsements

10 total 

Are you an attorney? Endorse this lawyer

  • Steven J. Topazio

    I endorse Brad. He is a highly skilled attorney that is well respected in the legal community and an asset to the profession.


    Steven Topazio Criminal defense Attorney
    Relationship: Fellow lawyer in community

  • Michael S. Waddington

    I endorse Richard. He is a highly skilled attorney that is well respected in the legal community.


    Michael Waddington Military law Attorney
    Relationship: Fellow lawyer in community

Contact info

Brad Bailey Law

10 Winthrop Square
4th Floor
Boston, MA, 02110


NYCurrently registered 198407/10/2016
We have not found any instances of professional misconduct for this lawyer.
Avvo contributions
Legal answers
Award nameGrantorDate granted
Super LawyerSuperLawyers2016
Super LawyerSuperLawyers2015
Super LawyerBoston Magazine2014
Super LawyersBoston Magazine2007
New England Super LawyerSuper Lawyers2007
Super LawyersBoston Magazine2006
Super LawyersBoston Magazine2004
Work experience
TitleCompany nameDuration
Managing PartnerBrad Bailey Law, P.C.2014 - Present
Partner, Chief of Criminal DivisionDenner Pellegrino, LLP2004 - Present
Association namePosition nameDuration
Massachusetts Bar AssociationMemberN/A
Legal cases
Case nameOutcome
United States v. David LaFleurNot Guilty
United States v. VaccaroNot Guilty
Commonwealth v. CarlsonGuilty - reduced charge of Manslaughter
See all legal cases 
Publication nameTitleDate
Inside the Minds (Aspatore Books)Handling Sex Crime Cases During a Time of Victim Rights2012
School nameMajorDegreeGraduated
University of Virginia School of LawLawJD - Juris DoctorN/A
Harvard CollegeN/AN/AN/A
Speaking engagements
Conference nameTitleDate
Top Guns: Criminal Law Mavericks Tell AllCriminal Defense2014