Peter Koutoujian: He's the Middlesex Sheriff. In Massachusetts, a sheriff is mostly responsible for prisoners. Koutoujian has been working for prison reform to make changes so that people who are released are less likely to return. I have no idea why someone would mount a challenge to him--he's generally popular, and I doubt that there's much risk of him losing the primary.
Bob Jubinville: He's the member of the Governor's Council from the second district (of eight). In most other states, the senate will approve gubernatorial appointments, but in Massachusetts, we have a separate body to do this. Jubinville has been very independent in his role, sometimes being the only vote against a nominee. He's very concerned that judges ruling on criminal cases have a good understanding of addiction, as that is often a significant factor in the circumstances leading up to the infraction. He makes a significant effort to attend public events throughout his huge district, so I see him regularly, which is not something you can usually say about someone in his office.
State Rep: If you're actually in my district (parts of Framingham and all of Ashland), let me know, and I'll fill you in.