[2] By age 22, he was focused with driving ambition, much to the credit of his friend Wayne Budd's father, an ex-Marine turned policeman in Springfield who took him under his wing and encouraged him to go to school.

He stayed there only a year, transferring to American International College in Springfield, Massachusetts, where he graduated on June 7, 1964.

For one year, Reilly lived in Dearborn, Michigan, where he worked with the Ford Motor Company as a Labor Relations Representative until 1967.

Reilly worked for two years as a prosecutor in the state Attorney General's civil rights division.

He ran for attorney general in 1998 against state Senator Lois Pines and won the Democratic Primary.

In the winter of 2001–02, he conducted a "very public investigation" into the sale of the Boston Red Sox to a group led by John W. Henry.

Reilly made "negative comments about the process, Major League Baseball's involvement in the sale, and threatened to block the transaction.

[7] On January 24, 2006, Reilly officially kicked off his first gubernatorial campaign in Springfield at his alma mater American International College.