Charles Street Jail

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In nearly a century and a half of continuous use, Boston’s Charles Street Jail was a bustling crossroads where the famous and infamous rubbed elbows. Everyone from Whitey Bulger to a captured German U-boat captain to a future mayor of Boston–to name just a few–served time there. When it opened in 1851, the Charles Street Jail was hailed as a model for the humanitarian treatment of prisoners. Over time, though, as the jail grew increasingly outmoded, its name became virtually synonymous with corruption, misery, and overcrowding. In a landmark legal case in 1973, the courts ordered the jail closed, finding its conditions so bad they violated inmates’ constitutional rights. After sitting vacant and deteriorating for many years, the magnificent, historic granite structure recently gained a new lease on life when it was renovated and transformed into a luxury hotel. Today, the building welcomes guests of a sort the old clientele could scarcely have imagined.