In January 1969, a dramatic incident occurred when three Penn Central locomotives derailed and blocked the northbound lane of the Southeast Expressway in South Boston. The locomotives, part of a freight train, were traveling on a bridge over the highway when the tracks gave way due to poor maintenance and the bridges deterioration. The engines fell onto the highway, disrupting traffic and causing a major scene. The Penn Central Railroad, which had formed only a year earlier from the merger of the Pennsylvania Railroad and New York Central, was already struggling financially and operationally, and the derailment highlighted the infrastructure issues plaguing the company. The incident underscored broader challenges in the rail industry at the time, contributing to Penn Centrals eventual bankruptcy in 1970.

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