When the New York, Westchester & Boston Railway opened in 1912, it was one of the engineering wonders of the American railroad world. Built to the highest level of engineering standards and operated with strict punctuality, the "Westchester" was a high-speed, high-capacity electric line designed to develop and serve upper-income communities in one of New York City's most rapidly growing suburban areas. Unbeknownst to most, reigning financial power J. Pierpont Morgan was behind the funding of the line.

Unrecorded millions, paid out for unknown reasons, raised the Westchester's construction total to a breathtaking $2 million a mile, almost $40 million a mile in 2005 dollars. Yet this railroad, designed to carry more than 100,000 people a day efficiently and comfortably, ran through virtually undeveloped territory and duplicated the line of the parent company that built it. Due to woeful financial performances and failure to show a profit, the Westchester trains stopped running within 25 years of their christening.