Editors at the "Chicago Tribune" noted his originality and growing popularity at the Journal and so made him a generous offer. Taylor accepted, and created and conducted his own column at the "Tribune" called "A Line o' Type or Two". He worked on the top floor of the new Tribune building, which was a seventeen-story skyscraper built in 1902 on the corner of Madison and Dearborn streets referred to as "Tribune corner". He conducted his column autonomously with little supervision for two years before resigning in 1903. He and Emma relocated back east and bought a home in Cos Cob (Greenwich) Connecticut while their daughter, Alva, attended Harvard. Taylor first wrote a column for the "Morning Telegraph" called "The Way of the World". Then in 1904, he became one of the contributing editors of "Puck", replacing W.C. Whitney who had died that year. During this time back east, he also contributed articles to the "New York Sun". Meanwhile, editors at the "Tribune" met little success in sustaining the same quality of Taylor's "Line". James Keeley, a hiring manager at the "Tribune", made a lucrative offer to Taylor in hope to lure him back to the paper. Taylor accepted the offer and returned to Chicago in 1909 where he resumed conducting his column without interruption until his death.