In 1836, Mr. Drew entered the banking business in Wall Street, and in 1840 established the widely-known firm of Drew, Robinson & Co.  This house engaged largely in the financial operations of the day, and became known as one of the most uniformly successful in its dealings of any in the city.  Mr. Drew remained at the head of it for thirteen years, but in 1855 withdrew to make room for his son-in-law, Mr. Kelley.  This gentleman died soon after his connection with the firm, and Mr. Drew resumed his old place.

Having succeeded so well in all his ventures, Mr. Drew now determined to enter another field.  Railroad stocks were very profitable, and might be made to yield him an immense return for his investments, and he decided to invest a considerable part of his fortune in them.  In 1855, he endorsed the acceptances of the Erie Railroad Company for five hundred thousand dollars.  This was the first decided evidence the public had received of his immense wealth, and in 1857 another was given by his endorsement of a fresh lot of Erie acceptances amounting to a million and a half of dollars.  This last indorsement was made in the midst of the great financial panic of 1857, and occasioned no little comment.  Men could admire, though they could not understand, the sublime confidence which enabled Mr. Drew to risk a million and a half of dollars in the midst of such a terrible crisis.  Some one asked him if he could sleep quietly at night with such large interests at stake.  “Sir,” he replied, calmly, “I have never lost a night’s rest on account of business in my life.”

In 1857, Mr. Drew was elected a director of the Erie Railroad Company, a position he held until recently.  He was subsequently elected treasurer of the company, and is one of the principal holders of Erie stock.  He is also one of the principal creditors of the company.  The recent proceedings in the New York courts to prevent the Erie Road from issuing the new stock necessary to complete its broad-gauge connections with the West, are too fresh in the mind of the reader to need a recital of them here.  It was proposed to issue ten millions of dollars worth of new stock, and Mr. Drew was to guarantee the bonds.  After a tedious and costly suit, in which the New York Central Road endeavored to prevent the issue of the stock, in the hope of keeping the Erie Road from forming through connections with the West, the New York Legislature legalized the new issue, and a compromise was effected between Mr. Drew, in behalf of the Erie Road, and Commodore Vanderbilt, who represented the New York Central.

Mr. Drew still continues his operations in Wall Street, where he is known as one of the boldest and most extensive, as well as one of the most successful, of all the operators in railroad stocks.  Though losing heavily at times, he has nevertheless been one of fortune’s favorites.  His efforts have not been confined to the Erie Road.  He owns stock in other roads, and, together with Commodore Vanderbilt, took up the floating debt of over half a million of dollars which weighed down the Harlem Road, and placed it in its present prosperous condition.