Dobelle grew up between Pittsfield, Massachusetts and Cocoa Beach, Florida, where his father served on the medical staff for Project Mercury.

[7][8][9] Long before the 1980 presidential race, Dobelle worked as a Research Associate for Governor Ronald Reagan's commission for educational reform.

While in San Francisco, Dobelle decentralized administrative functions - a managerial model the college celebrated and maintained until it went into state receivership in 2012 nearly losing its accreditation.

[13] As president of the University of Hawaiʻi from 2001 to 2004, he backed unifying the system's campuses, established the Academy of Creative Media, built a new medical school, reformed financial and building practices and strengthened Native Hawaiian programs.

He was also criticized[14] for politicizing the university by endorsing Democrat Mazie Hirono for governor and for paying unusually high salaries to administrators (though typical by mainland standards).

[17][18][19][20][21][22][23][24][25][26][27][28][29][14][30][31][32][33][34][35][36][37] The ensuing controversy caused a statewide referendum to be passed by 63% that changed the way Regents were appointed by the Governor and was upheld unanimously by the Hawaii Supreme Court.

Dobelle reorganized and focused the organization on core issues of access and affordability, significantly heightening NEBHE's visibility and increasing external funding.

Reaction to the controversy includes an investigation by the state Attorney General's office and the withdrawal of a $100,000 gift; Dobelle countered that the pledge had been made years before and was not authentic.

Dobelle has received accolades during his career for success in community outreach as well as management of colleges inclusive of faculty issues, athletic teams, student engagement and being an agent for change.