[citation needed] Depew attended Peekskill Military Academy for 12 years before matriculating at Yale College in 1852.

[3]: 165  At Yale, he was a classmate of two future United States Supreme Court Justices, David Josiah Brewer and Henry Billings Brown.

After graduating from Yale, Depew apprenticed in the office of Edward Wells in Peekskill and read law with William Nelson.

He was admitted to the New York state bar in March 1858 and opened an office in Peekskill, where he practiced until 1861.

Having earned recognition for his work with subsidiary companies, Depew became general counsel and director of the entire "Vanderbilt System" in 1876.

He joined the executive board of the New York Central & Hudson River Railroad in 1882 and became its second vice president.

As a young student and lawyer, Depew stumped the state of New York for John C. Frémont in 1856 and for Abraham Lincoln in 1860.

[10] On October 7, 1897, Depew inaugurated the New York pneumatic tube mail, declaring: "This is the age of speed.

He made presidential nominating speeches for Benjamin Harrison in 1892 and Governor Levi Morton in 1896.

Depew was a candidate for United States Senator in an 1881 special election, but withdrew his name from consideration after the 41st ballot.

In 1906, David Graham Phillips began a muckraking series entitled "The Treason of the Senate" for William Randolph Hearst's new Cosmopolitan magazine, and targeted Depew in the first article.

The article's sensational charges included labeling Depew a "boodler" owned "mentally and morally" by railroad magnates Cornelius and William Vanderbilt.

The piece provoked outrage from President Roosevelt, the New York Sun and Senator Henry Cabot Lodge.

[citation needed] He served as trustee of his alma mater, the Peekskill Military Academy.

[17][18] In a 1925 interview aged 90, Depew clarified that he had never been a vegetarian but in his early 60s removed red meat from his diet but consumed poultry.

[19] Depew was remembered as a prodigious speaker years after his death; many years after his death, Senator Robert S. Kerr of Oklahoma quoted Depew in an attack on a Senator from Indiana: "As I gaze on the ample figure of my friend from Indiana, and as I listen to him, I am reminded of Chauncey Depew who said to the equally obese William Howard Taft at a dinner before the latter became President, 'I hope, if it is a girl, Mr. Taft will name it for his charming wife.'

'"[20] In 1929, May Palmer-Depew donated her late husband's papers and $120,000 to establish a department of public speaking to George Washington University.

[24] The ship Chauncey M. DePew was built for the Maine Central Railroad Company in 1913 to carry passengers to Bar Harbor.

She worked along the Maine coast until 1925 when she was sold to the Day Line as an excursion boat between New York and Albany.

In 1940 she was drafted to carry men and supplies between New York City and Fort Hancock on Sandy Hook.

Back in the States, in 1971, a storm slammed her against a breakwater in Chesapeake Bay, where she lay for three years.

The Swiss-born American artist Adolfo Müller-Ury painted Depew numerous times.

A three-quarter length portrait of Depew seated on a bale of furs was exhibited at the Paris Salon in 1890 and is now in the Yale Club of New York City.

Copies of an etching Müller-Ury made of Depew, signed by the artist and the sitter, are in the American National Portrait Gallery in Washington, DC, the collection of the Newport Preservation Society of Rhode Island, and the University of Cincinnati College of Design.

In 1896, sculptor Victor D. Brenner created a small plaque in honor of his 60th birthday (which was two years earlier).