[citation needed] Liebowitz was Middlebury's third faculty member to become president, following McCardell and 19th century alumnus Ezra Brainerd.

In his first year, he shaped the agreement that brought the Monterey Institute of International Studies under affiliation with Middlebury, and began a comprehensive strategic planning process.

Liebowitz kicked off The Middlebury Initiative in October 2007; the largest capital campaign ever by a liberal arts college, the Initiative will raise $500 million to support the strategic plan's primary goals of financial aid and additional faculty.

[4] On December 17, 2015, Liebowitz announced that he would begin serving in a leadership role at Brandeis University effective July 1, 2016.

"[5] However, on April 9, 2021, the Board of Trustees announced a five-year contract extension on Liebowitz's presidency.