• Howie Winter's history in the Boston underworld


    Howie Winter's arrest at the age of 83 is an unexpected twist in the life of a gangster many thought had given up the hard way of the streets for an anonymous existence in a quiet subdivision in Millbury.

    Seeing Howie Winter in Somerville District Court on Friday, it is hard to imagine the young man who eventually led the notorious Winter Hill Gang.

    Headquartered in the infamous Marshal Street Garage on Somerville's Winter Hill, the gang's members included the likes of now familiar mobsters James "Whitey" Bulger, Stephen "The Rifleman" Flemmi, and John Martorano.

    Howie Winter took over Winter Hill when its leader, Buddy Mclean, was murdered near the end of the Irish gang wars.

    The Winter Hill Gang made most of its money plying the trade of most mobs. Their operations included truck hijackings, extortions, and rackets. However, it was a horse race fixing scandal that ended Howie Winter's reign.

    Winter, along with the rest of the gang, was indicted in the late 1970's for a horse race fixing scheme, but two names were pulled off the indictment at the last minute: Bulger and Flemmi. The men were FBI informants, and in this matter, they become unindicted co-conspirators.

    Winter went to jail, while Bulger and Flemmi consolidated power and their grip on the Boston underworld for years.

    Howie Winter has been out of trouble since 2002. Now, at the age of 83, if he's convicted on new extortion charges he could be put away for good.

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