The IRT’s Dyre Avenue line is the remnant of the New York, Westchester & Boston Railway, the Road of Ease, which ran safe, stylish, and efficient trains on time from 1912 to 1937 – and never made a dime. Incorporated in 1872 to build from the Harlem River north to Connecticut, the Westchester collapsed in the Panic of 1873 and slumbered for a generation as a file in its lawyers’ office. In 1906, the J.P. Morgan interests bought this paper railroad for $11 million. Its franchise – the right to build and operate a railroad – justified the expense to the president of the New York, New Haven & Hartford Railroad, Charles Mellen.

Mellen enjoyed the confidence of Morgan, whose domination of the New Haven had made it a monopoly of southern New England’s transportation. Through construction, stock purchase, or lease, the New Haven controlled nearly every railroad and trolley line in Connecticut, Rhode Island, and southern Massachusetts, and even coastal shipping.

As planned, the Westchester would compete with its parent for commuters. Yet Mellen reasoned this would save the New Haven money. The Interstate Commerce Commission (ICC) compelled the New Haven to operate cheap commuter trains into Grand Central Terminal, which was owned by the rival New York Central. By assessing extortionate terminal charges for each New Haven passenger, the NYC made its competitor lose money on every rider. The Westchester would avoid these charges by terminating at 132nd Street and Willis Avenue, where its riders would transfer to the subway or the Third Avenue El. Fewer New Haven commuters meant smaller losses.

Moreover, in common with the city fathers who planned the convergence of roads, railroads, and subways at the 149th Street Hub, Mellen believed New York’s commercial district would expand ever northward, reaching the South Bronx around 1940. The Westchester would be waiting for it.

Mellen built a four-track heavy-duty electric railroad along a straight, level right-of-way to White Plains and Port Chester. On opening day, May 29, 1912, passengers entered its handsome Spanish Renaissance stations to find, as Roger Arcara wrote, “the culmination of railway development: the most modern and efficient design, the most solid and sturdy construction, the greatest capacity (for its amount of trackage), and the most attractive layout and appearance of any line in the world.”

But as early as 1907, future U.S. Supreme Court Justice Louis Brandeis had charged Mellen’s profits were mere bookkeeping magic. In May 1912, a few days before the Westchester accepted paying passengers, a routine ICC audit found odd transactions between the New Haven and its 336 subsidiaries. The ICC found the New Haven had inflated profits by lending money to subsidiaries, which they used to pay dividends to the New Haven, which was reported as income. Mellen had further cooked the books with hundreds of fictitious asset sales among subsidiaries. One example outlined by George Foster and Peter Weiglin involved the New Haven’s steamships. In 1907, they were sold by one subsidiary, New England Navigation, to another, Consolidated Railway. Consolidated Railway paid for them with stock, worth $20 million because Mellen claimed that was its value. The transaction yielded a paper profit for New England Navigation and an increase in Consolidated Railway’s assets. The same steamboats had since shuttled from Consolidated Railway to New England Steamship to New England Navigation and back as needed. With each such transfer, the books became fictions showing explosive growth in income despite no real increase in value. Mellen resigned in August 1913. The ICC then granted him immunity from prosecution for his testimony, which led to federal indictments for 21 New Haven directors.

Meanwhile, the Westchester operated at a loss, surviving on advances from its parent. Most commuters preferred a one-seat ride to Midtown over changing trains at Willis Avenue. The 1916 zoning laws halted commercial development at 59th Street. And the Westchester carried little freight: a train of coal up to White Plains in the fall and the ashes out in the spring.

In 1935, the New Haven went broke. Its advances stopped. The Westchester, too, filed for bankruptcy. The New Haven’s 1935 annual report reads, “The advances (to the Westchester) amount to $21,460,494.87, but as the prospect of their being repaid is very remote, they have been reduced to a nominal value of $1.00.”

Hopelessly insolvent, the Westchester ran its last train on December 31, 1937. The New York City government restored service between East 174th Street and Dyre Avenue on May 15, 1941, having paid $1.7 million for the trackage, much less than its construction cost. The East 180th Street and Morris Park stations still bear the initials “N.Y.W.B.” and the overpass at Brady and Matthews Avenues bears the railroad’s herald: a caduceus, a staff entwined with coiled snakes, the emblem of Mercury, swift messenger of the gods.