Originally an offshoot of a land development venture, the West End rose to prominence when it merged several independent streetcar companies into a single organization, and over the next decade it was the primary operator of public street transit within the Boston area.

[6] Originally, the West End intended to coordinate operations with the principal companies in order to gain access to the Boston downtown; these efforts were however stymied by the directors of the Metropolitan and the Cambridge, who feared that the new organization represented a threat to their interests.

For their part, proponents argued that the move would put an end to the inefficiencies of having competing railways (which had been held to blame for high levels of congestion and blockades on the streets of Boston), and a general improvement in service would be achieved as a result.

[10] In remarks made to stockholders shortly after the merger, Whitney himself defended consolidation on the grounds that "the blockades occurring on the principal thoroughfares" in Boston had reached the point of requiring a remedy, and that "if [the West End] had not taken hold of this matter the city would surely have done something [instead].

[17][18] One of the largest challenges facing the West End during its history was in dealing with a massive rise in passenger usage, which resulted in ever-increasing levels of congestion on Boston city streets during the 1880s and 1890s.

At first the management of the West End were slow in their efforts to address the issue, but in order to head off potential competition from rival companies they eventually offered several proposals for establishing rapid transit lines to relieve traffic within the city.

In July 1890 the state legislature passed a measure authorizing the company to construct elevated railroads,[20] and three months later Whitney unveiled a plan for a main line running between Roxbury and Charlestown.

[22] Other proposals for the West End, including a highly controversial idea for a rail running through the Boston Common, were similarly never carried out, and ultimately no elevated or dedicated lines were put into place by the company.

In December 1896 the West End signed an agreement with the Transit Commission to lease the tunnel, known as the Tremont Street Subway (now the central part of the Green Line), for a period of twenty years upon completion.

Within a year of Boston Elevated's incorporation, the group behind it realized that they would be unable to raise sufficient capital to develop their proposed railway, and attempted to sell their charter off to a variety of parties, including the West End.

The group, which included Eben Dyer Jordan and William Bancroft and which was financially backed by Kidder, Peabody & Co. and J.P. Morgan, quickly acquired a controlling interest in the Boston Elevated and attempted to do the same with the West End.

Following a highly-publicized proxy fight, the Kidder-Morgan faction managed to gain control of the board at the annual shareholders' meeting in November 1896, and a short time afterwards plans were formed to lease the West End system to the Boston Elevated on a long-term basis.