[1] In 2010, Drenttel was elected to the Art Directors Hall of Fame and the Alliance Graphique Internationale, and was the first Henry Wolf Resident in Graphic Design at the American Academy in Rome.
In 1984, after the breakup of AT&T, Drenttel won and managed the cellular telephones advertising accounts for two of the regional Bell Operating Companies, Ameritech and Pacific Telesis.
Additional selected clients over a 12-year period included Brooklyn Academy of Music, Champion Paper, Elektra Records, Farrar Straus & Giroux, HarperCollins, Hewitt Associates, Inc. Magazine, Metropolitan Transportation Authority, Museum of Modern Art, National Audubon Society, The New Republic, Olympia & York, Springs Industries, St. Vincent's Hospital, and Wildlife Conservation Society.
[7] Additional clients included Yale University Press, Errol Morris, Stora Enso, Global Centre for the Responsibility to Protect, Smithsonian Archives of American Art, Children's Television Workshop, among others.
Books published included works by Paul Auster, Thomas Bernhard, Michael Bierut, Paul Celan, Gloria Feldt, Grolier Club, Jessica Helfand, William Helfand, Siri Hustvedt, Hans Erich Nossack, James Salter, Susan Sontag, Leon Wieseltier and Hanns Zischler.
Additionally, Winterhouse published Below the Fold: an occasional journal exploring topics through visual narrative and critical inquiry.
[10] Drenttel established Winterhouse Institute in 2006 with the intent to focus on non-profit projects that support design innovation and education, as well as social and political initiatives.
A collaboration with AIGA, the $10,000 award (along with additional $1,000 student prizes) recognized excellence in writing about design and encouraged the development of new young voices.
Polling Place Photo Project was launched by Winterhouse Institute in October 2006 before the mid-term elections (in collaboration with AIGA).
[12] Winterhouse Institute was awarded a $1.5 million grant by the Rockefeller Foundation in late 2008, supporting a three-year project to develop collective action and collaboration for social impact across the design industries.
Teach For All acts as a global network of independent social enterprises that are working to expand educational opportunity in their nations by enlisting their most promising future leaders in the effort.
In 2005, Drenttel assumed the role of national task force director for disaster relief for designers after the destruction of the Gulf States by hurricanes.
Drenttel served as board member and corporate advisor of Academic Partners LLC, a publishing company focused on the higher education marketplace from 1999 to 2002.
From 2002 to 2006, Drenttel served as creative director for the Nextbook Foundation, which promoted books illuminating Jewish literature and culture.
[21] Drenttel served as board member of the organization from 1993 to 1999, and vice president from 1997 to 1999, where he was responsible for strategic planning and the national expansion of the “Poetry in Motion” program to 20 transit systems nationwide.
Drenttel was a fellow at the New York University Institute of the Humanities since 2003, an organization that promotes the exchange of ideas between academics, professionals and the general public.