[1] After leaving Eastman's College, Woodruff went to New York City where he was hired as a clerk for a wholesale salt supplier.

[1] Woodruff also became involved in warehousing on the Brooklyn waterfront, gaining a controlling interest in several commercial frontages and two grain elevators.

Woodruff later purchased additional land in the Adirondacks, where he developed a popular commercial camp called Kamp Kill Kare.

[1] Woodruff rose through the party ranks, being elected as a delegate to the 1888 Republican National Convention which nominated Benjamin Harrison for President.

[1] On the evening of September 29, 1913, Woodruff experienced an attack of "apoplexy" (stroke) while speaking at a political event at Cooper Union in New York.

Upon taking the stage he reportedly commented, "My legs feel queer," but proceeded to give his speech before eventually collapsing.

"[7] His funeral was held at the Central Congregational Church in Brooklyn on October 15, and he was buried in Green-Wood Cemetery.