An important figure in the creation of the Republican Party in the mid-1850s, and a supporter of the Union during the American Civil War, he was most notable for his service as a U.S. Representative from New York.

A native of Greenfield Hill, Connecticut, Wakeman completed a college preparatory education, taught school while studying law, and attained admission to the bar in 1847.

In his later years, Wakeman was one of the developers of Coney Island as a resort and amusement destination, and realized a substantial profit when he sold out to a syndicate of investors.

[6] In the early 1840s, Wakeman became active in politics as a Whig, and he became a colleague of Thurlow Weed, William H. Seward, and Henry Jarvis Raymond, the leaders of the party in New York state.

[4][8] As was the usual custom, Wakeman resigned before the unit left for the front lines, and was succeeded by James Miller, a veteran of the Mexican–American War.

[11] When New York City opponents of the Lincoln administration and military conscription rioted in 1863, Wakeman was singled out because he was a prominent federal official; a mob broke into his Yorkville home to steal all the clothing and furniture, then burned the house to the ground.

[9] During the 1864 United States presidential election, some prominent northern newspaper publishers and Democrats advocated for a negotiated peace with the Confederacy.

[12] Though he doubted their efforts would bear fruit, Lincoln authorized Horace Greeley to meet with Confederate commissioners in Niagara Falls, Ontario.

[13] Afterwards Lincoln worked to persuade pro-peace Democrats in the north to support his re-election, including asking Wakeman to intercede with James Gordon Bennett Sr. of the New York Herald.

[14] When Mary Lincoln's compulsive shopping caused her to incur a large debt to New York City retailers, Wakeman aided her to refinance her obligations so her husband wouldn't find out.

[9] He made a substantial profit in the late 1870s when he sold his interests in Coney Island to a syndicate led by businessman Austin Corbin.