221 Whitney Avenue currently consists of a rectangular, six-story, modern, metal and limestone office building, shown recently in exhibit 1, with a detached four-story molded circular concrete parking garage and surface parking (exhibit 2). It is the home of Yale University’s Organizational Development and Learning Center. The main office structure was completed in 1957 while the parking garage was added sometime before 1973. Details of the building’s make and history are chronicled in a Historic Resources Initiative Report from 1980 (exhibit 3).



The first and only other structures to stand at 221 Whitney Avenue were built in 1890. In the years leading up to development on the land, maps of Whitney Avenue between Bradley and Humphrey (exhibit 4, exhibit 5) show only four large estates on the eastern side of the street; 221 Whitney appears as an undeveloped portion of a larger estate. It was eventually separated from the larger plot, and was even halved briefly itself (exhibit 6). Each of these two plots traded owners twice over the course of the 1880’s without any development occurring on the property.



Following the death of her husband John Jarvis Matthias, Jane Keeler Matthias bought the two lots which came to composite 221 Whitney Avenue and had a 24-room, wood and stone residence with detached carriage house built on the site. Her late husband was a graduate of the Sheffield Scientific School, the son of a prominent New York Methodist Minister, and in the shipping business ; all signs indicate the family was well-to-do. As noted in a New Haven Register article written on the occasion of the home’s demolition (exhibit 7), in moving to Whitney Avenue, Jane Matthias was one of the first of many to leave downtown for what were then the outskirts: “Mrs. Matthias lived on Chapel Street, opposite the former Grace Hospital, before building the spacious home on Whitney Avenue. At that time, friends told her she was moving ‘too far out,’ and pointed out that the horse cars of the era ran only as far as Humphrey Street. In subsequent years, a great many fine homes were built along Whitney Avenue.”



After six years of living at 221 Whitney Avenue, Jane Matthias died on October 4, 1896, leaving the property to her daughter Mary Elsa Matthias. Less than a week later, on October 12 of that same year, Elsie Matthias married General Phelps Montgomery and the two moved into the inherited home, labeled in a 1904 photograph as the “Home of General Phelps Montgomery” (exhibit 8). Phelps Montgomery was, at the time, a student at the Yale Law School, but already carried distinction as a former member of the Oregon National Guard, a Yale College graduate and the grandson of Missouri Governor John Phelps. General Montgomery would go on to practice law in New Haven, holding offices on Church Street downtown. He was honored as one of Connecticut’s delegates to the Louisiana Purchase Exhibition in 1904 and with an appearance in “Who’s Who in New England” in 1915. He would serve as judge-advocate-general on the staff of Governor McLean and as alderman for New Haven’s Eighth Ward. General Montgomery was a member of the New Haven Lawn Club, located on Whitney Avenue. The Montgomerys appear to have been active and respected residents of the Avenue, New Haven, and Connecticut. They had six children.



Upon her death on May 29, 1947, Elsie Montgomery left 221 Whitney Avenue to her husband. In case of his remarriage or death, however, her will dictated that the home remain in the family, passing to three of her six children—Russell, Elsie Matthias, and Mary Marjorie. Phelps occupied the home until his death on November 13, 1954, at which time it was inherited by the three children. At the time of the sale 1956, the Register lists the house as occupied not only by Russell, Elsie, and Mary Montgomery, but their brother Ralph and his two children as well.



In 1956, the Montgomery children sold 221 Whitney Avenue to Connecticut Medical Service insurance company and the Matthias-Montgomery home was quickly demolished. Indeed, the New Haven Register noted a trend in such demolitions in the aforementioned article, titled “Whitney Avenue Loses Another Fine Residence in March of Progress” (exhibit 7); at the time of construction, both older homes and newer office buildings were visible along Whitney Avenue (exhibit 9, exhibit 10). Construction of the new offices for Connecticut Medical Service, which had previously been located at 205 Whitney Avenue, lasted from September 1956 to November 1957. Richard H. Fletcher, one of six architects employed by the Office of Douglas Orr, then located at 111 Whitney Avenue, designed the building.



Connecticut Medical Service remained at 221 Whitney Avenue through its transition to Blue Cross/Blue Shield of Connecticut and later to Anthem Blue Cross/Blue Shield; the art-deco insignias between the first and second story windows were altered to reflect the first change in name (exhibit 11, exhibit 12). However, in the 1980’s, the building’s office space was divided and leased to other tenants: the third through sixth floors to Southern New England Telephone Company in 1984; the first and second floors to Community Health Plan in 1987; and the sixth floor and basement to Promed Systems also in 1987. These leases also stipulated the divisions of parking spots in the 221 Whitney garage.



In 1998, Anthem Blue Cross/Blue Shield, which had moved offices to 370 Bassett Road in North Haven, sold 221 Whitney Avenue to Yale University for $2,500,000. With this change of ownership came changes to the building’s exterior—namely, the removal of Blue Cross/Blue Shield motifs above the first floor windows and entryway and the addition of Yale signage. Today, the building also features informal decoration placed in office windows (exhibit 13).