He later transferred to the auditing department and was chief clerk in the Mayor's office during James Michael Curley's 1922 to 1926 term.

[5] He was discharged that December due to a reoccurrence of a chronic ear issue and returned to the city clerk's office.

The Massachusetts General Court passed emergency legislation to bypass council president John B. Kelly, who had recently been acquitted on bribery charges and was in ill health, and to grant full mayoral powers to Hynes (who as city clerk was second in the line of succession) until Curley's release from prison.

"[10] Stung by this off-hand but disparaging comment about his performance as acting mayor, Hynes decided to challenge Curley in the November 1949 election, and defeated him.

[13] His second child, Marie "Darby" Hynes Gallagher, was a special education teacher in the Boston city school system.