CONTROVERSIA Support the projectOptional · no effect on content
Portrait not available

Born in United States · Nationality American — organised crime / Winter Hill Gang / racketeering / drug trafficking

Howie Winter

Organised crime and cartels

Documented profile covering 9 controversies, including “1965–1979: leadership of Winter Hill Gang after Buddy McLean's death” and “1973: mistaken killing of bartender Michael Milano attributed to Winter by John Martorano, but never prosecuted”.

Are you concerned? Right of reply

Profile No. 1993 · Updated on 12 October 2026

9Documented controversies
7Sources
1Formal charge · all time1 followed by a conviction
4Convictions

§ Legal statuses reflect the documented sources as of the date shown; they replace neither court decisions nor the presumption of innocence. Counts are not a rating. Methodology

I. Documented controversies

01

June 2012

2012: further arrest for attempting to extort $35,000 from two men

Conviction

At more than 80 years old, Winter was accused of trying to extort $35,000 from two men. He eventually pleaded guilty to an extortion charge and received a probation sentence.

State of the evidence
Established by a court
Attribution
Directly implicated

Sources · 2

  1. [1]
    The Boston GlobeHowie Winter, former head of Winter Hill Gang, arraigned in Somerville District CourtPressHigh reliability
  2. [2]
    The Boston GlobeFormer Winter Hill Gang leader Howie Winter has diedPressHigh reliability

Last verified: 14 September 2026

Add to this entry

Case · 2 documented stages

1992–1993: indictment followed by substantial federal sentence in cocaine case

Conviction
02

1992–1993

1992–1993: indictment followed by substantial federal sentence in cocaine case

Conviction

Winter was prosecuted and then convicted in the cocaine trafficking case. Press and judicial sources reported a sentence of approximately ten years.

Attribution
Directly implicated

Sources · 2

  1. [1]
    U.S. District Court for the District of Massachusetts / JustiaUnited States v. Winter, 826 F. Supp. 33Court decisionVery high reliability
  2. [2]
    The Boston GlobeFormer Winter Hill Gang leader Howie Winter has diedPressHigh reliability

Last verified: 14 September 2026

Add to this entry

03

1990–1991

1990–1991: involvement in cocaine trafficking documented through several controlled purchases

Conviction

A federal and local investigation documented a cocaine supply relationship and several controlled purchases by agents or informants, with Winter acting as an intermediary or supplier.

Attribution
Directly implicated

Sources · 2

  1. [1]
    U.S. District Court for the District of Massachusetts / JustiaUnited States v. Winter, 826 F. Supp. 33Court decisionVery high reliability
  2. [2]
    U.S. Court of Appeals for the First CircuitUnited States v. Winter, 94 F.3d 640Court decisionVery high reliability

Last verified: 14 September 2026

Add to this entry

04

1965–1979

1965–1979: leadership of Winter Hill Gang after Buddy McLean's death

No legal proceedings

Following Buddy McLean's death, Howard 'Howie' Winter became the principal leader of the Winter Hill Gang, an organised crime network in the Boston area.

State of the evidence
Documented
Attribution
Directly implicated

Sources · 1

  1. [1]
    The Boston GlobeFormer Winter Hill Gang leader Howie Winter has diedPressHigh reliability

Last verified: 14 September 2026

Add to this entry

Case · 2 documented stages

1979: federal conviction for racketeering and sporting corruption, ten years in prison

Conviction
05

August 1979

1979: federal conviction for racketeering and sporting corruption, ten years in prison

Conviction

Following a 46-day trial, Winter was convicted of RICO and sporting corruption offences connected with race fixing. He received a ten-year federal prison sentence.

State of the evidence
Established by a court
Attribution
Directly implicated

Sources · 2

  1. [1]
    U.S. Court of Appeals for the First Circuit / JustiaUnited States v. Winter, 663 F.2d 1120Court decisionVery high reliability
  2. [2]
    U.S. Court of Appeals for the First Circuit / JustiaUnited States v. Winter, 730 F.2d 825Court decisionVery high reliability

Last verified: 14 September 2026

Add to this entry

07

December 1973–November 1975

1973–1975: extensive horse-race fixing scheme

Conviction

Winter and his associates ran a RICO enterprise aimed at fixing horse races, notably by bribing jockeys and then betting on the manipulated results.

Attribution
Directly implicated

Sources · 1

  1. [1]
    U.S. Court of Appeals for the First Circuit / JustiaUnited States v. Winter, 663 F.2d 1120Court decisionVery high reliability

Last verified: 14 September 2026

Add to this entry

06

années 1970–1979

Late 1970s: state sentence of nine to ten years in extortion case involving gambling machines

Conviction

At the time of his federal conviction, Winter was already serving a state sentence of nine to ten years in an extortion case involving, among other matters, gambling machines.

State of the evidence
Documented
Attribution
Directly implicated

Sources · 2

  1. [1]
    U.S. Court of Appeals for the First Circuit / JustiaUnited States v. Winter, 730 F.2d 825Court decisionVery high reliability
  2. [2]
    The Boston GlobeFormer Winter Hill Gang leader Howie Winter has diedPressHigh reliability

Last verified: 14 September 2026

Add to this entry

08

1973

1973: mistaken killing of bartender Michael Milano attributed to Winter by John Martorano, but never prosecuted

Protagonist not prosecuted

Protagonist not prosecuted — these proceedings are not counted in their formal charges or convictions.

At James Bulger's trial, John Martorano testified that he and Winter had fired at the wrong car while seeking a rival, killing young bartender Michael Milano.

Attribution
Directly implicated
Role of the person profiled
Protagonist not prosecuted

Sources · 2

  1. [1]
    The Boston GlobeAt Bulger trial, John Martorano describes 1973 mistaken-identity shootingPressHigh reliability
  2. [2]
    The Boston GlobeFormer Winter Hill Gang leader Howie Winter has diedPressHigh reliability

Last verified: 14 September 2026

Add to this entry

09

années 1960–1970

1960s–1970s: other murders attributed to Winter in gang war accounts, without conviction

No legal proceedings

During trials linked to the Winter Hill Gang, former associates connected Winter with several homicides committed during Boston's gang wars.

State of the evidence
Reported by the press

Sources · 1

  1. [1]
    The Boston GlobeFormer Winter Hill Gang leader Howie Winter has diedPressHigh reliability

Last verified: 14 September 2026

Add to this entry

II. Constellation of documented links

No documented link with another published profile for now.

Two profiles are linked when a documented controversy of one names the other. The link points to that controversy and its sources; it does not indicate a personal relationship.

III. Has something changed?

A new court decision, a missing source, a mistake? Tell us what should be updated: every request is read by the editorial team.

Support the archive

Controversia checks and updates its profiles independently. Support is optional and has no effect on the content of profiles.

Donate

Update request

Howie Winter

Say which controversy is concerned and, if possible, give a source. Between 10 and 2,500 characters.

0 / 2500

To prevent abuse, the approximate location of your connection is recorded with your request.

iPhone and iPad

Install Controversia

  1. Tap Share
  2. then Add to Home Screen

Tap Share, then Add to Home Screen.