Connolly is son of a United States Navy officer and spent his childhood as a military brat, living in San Diego, Boston, Naples, Muskogee, Oklahoma, and Norfolk, Virginia before settling down in Washington, D.C.[1][2] After a few semesters at the University of Atlanta, Connolly transferred to George Washington University, where he graduated with a degree in finance and marketing in 1971.
He sold the firm in 1983 to become vice president for sales and marketing for American Sign & Indicator, the world's largest manufacturer of scoreboards.
[1] In July 1985, Connolly joined A Beeper Co., a Bell Atlantic subsidiary that provided and serviced paging equipment, as vice president of sales and marketing.
They also sought to make the team more accessible by putting its games on FM radio station and having players travel in caravans to neighboring states.
[10] After leaving, Minnesota, Connolly joined an equity firm that attempted to purchase the National Hockey League's Phoenix Coyotes.