Thomas Underwood is perhaps most celebrated as "the man who made First Street West". He was a distinguished developer in Calgary and is responsible for many buildings not only along First Street West, but also throughout all of Calgary. The first"" Underwood Block was built 1910 at the corner of 1st Street West and 10th Avenue. A few years later, another larger and more extravagant block was constructed further up First Street and it too was known as the Underwood Block. Eventually, Mr. Underwood had to change the name of the original Underwood to the Western Block which remains standing today. Unfortunately, the second Underwood Block was ravaged by fire in the late 1980's resulting in the demolition of the northern component of this complex. The southern section, including the tower, exists today as offices and restaurant.Also recognized for his community work, Underwood was the director of the YMCA for 25 years as well as the President for the Chinese YMCA and the President of the Baptist Convention Board of Alberta. In 1893, he was elected as a City Alderman, and between 1901 and 1902 he served as Calgary's 13th Mayor.

Not to be over looked, Mrs. Kate Underwood was also an Underwood of some notoriety. She devoted her life to YWCA work, from the construction of the YWCA building to volunteering at the Community Association whenever she could. Through this work, she became known as a woman bent on mothering the girls of strangers.