On December 10, 1995, Evan S. Dobelle was chosen by the Trinity's Board of Trustees to be the College's next president after a nine-month nationwide presidential search. Dobelle was then inaugurated as Trinity's 18th president on October 1, 199, and served the College until 2001, during which he implemented many to connect the community and the College, the most notable being the Learning Corridor Initiative. He was determined to make Trinity a place where students could receive an “incomparable liberal arts education while still being able to take advantage of the opportunities present in an urban city such as Hartford.”

Dobelle received his bachelor's, master's, and doctoral degrees in Educational Administration from the University of Massachusetts (Amherst) and a Master's in Public Administration from Harvard University. Before coming to Trinity, Dobelle had a robust political career. He served as the executive assistant for U.S senator, Edward W. Brooke (1971-73); United States Chief of Protocol (1977-79); chief financial officer and treasurer for the Democratic National Committee & national finance chairman for the Democratic Party and President Jimmy Carter (1979-81); President of Middlesex Community College (1987-90; and President and Chancellor of the City College of San Francisco (1990-95).

During Dobelle's presidency, the college underwent some noteworthy changes including, bettering the public image of the college leading to an increase in applicants and attendance, contributing greatly to Trinity's fundraising efforts raising millions for the college, and the construction of the Learning Corridor, a $200 million project to improve Trinity's relationship with the Hartford community. These initiatives led by Dobelle helped revamp Trinity's reputation not only in Hartford but across the nation, and the college was able to reclaim its title as one of the best small liberal arts colleges in the US.

In 2001, Dobelle announced his departure from Trinity as he accepted an offer to be President at the University of Hawaii. In his short years as president, he helped transformed Trinity from a struggling regional liberal arts college to a bolstering place of learning and diversity with a focus on the importance of connecting with the community beyond the corners of Trinity.

The Trinity Tripod 03/13/2001

The Trinity Tripod 01/27/1999

Trinity Reporter 05/1995

The Trinity Tripod 12/11/1994