[2] While working in the health department, O’Connor attended Suffolk University Law School at night.

[2] O'Connor represented Eugene R. Drioly, a convicted murderer who was seeking a pardon, pro bono.

He finished a distant third behind James Michael Curley and John R. Murphy in the 1921 Boston mayoral election.

[2] O’Connor chose not run for a second term on the school committee in 1923, instead focusing on his law practice.

[6] O’Connor ran for clerk of the Massachusetts Supreme Judicial Court in 1928, but lost by a few hundred votes.