[2] He was a descendant of John Keep,[3] and emigrant from the Kingdom of England who arrived in the Massachusetts Bay Colony in 1660[4] and was killed in 1676 during King Philip's War.

His family was left impoverished and lost their home, so his mother turned herself and her children over to the county poorhouse.

The county loaned children out as workers to local businessmen and farmers, if the employer provided a wage or some other means of improvement to the child.

Keep was sent to work for Joseph Grammon, a local farmer who promised to send the boy to public school.

[3] He then invested in notes issued by the state, which were trading at a discount due to the economic recession.

He then began traveling around upstate New York, where he would approach people carrying Canadian banknotes.

[7] He also made bold trades in undervalued railroads, earning hundreds of thousands of dollars.

The firm was one of Wall Street's leading brokerage houses, Lockwood was a longtime ally of Cornelius Vanderbilt.

Together, the two men manipulated the stock of the Michigan Southern and Northern Indiana Railroad in the 1850s, buying large quantities whenever they forced the price down.

Beginning in 1865, Cornelius Vanderbilt began to wage a long and bitter war for control of the Central.

The Central was governed by a clique of men known as the "Albany Regency", and controlled most of the rail traffic outside of New York City.

The contract also required the Central to pay the Hudson River Railroad $100,000 a year ($1,948,085 in 2023 dollars) for keeping extra rolling stock on hand in the summer to handle the increased traffic moving north.

Steamboats could not move the Central's cargoes because the Hudson River was frozen due to a harsh winter.

In an attempt to make money off the situation, Keep borrowed a significant number of shares to sell short.

This forced Keep to pay his lenders out of his own pocket, hurting him financially, and allowed the Vanderbilt group to gain control of the Central.

[20] Keep partnered with investor Rufus Hatch,[23] and won control of the Chicago and North Western Railway in 1867.

[16][26] Marvin Hughett, a veteran manager of the company, convinced him to finance a massive expansion of the railroad's system.

[29] Keep married Emma Woodruff, daughter of a prominent Watertown hotel owner and real estate developer,[7] in 1847.

It also owns and maintains the Ives Hill Retirement Community as well as Keep House, a place for out-of-town families to stay while their loved ones are receiving medical care at the local hospital.