Longtime Boston political analyst Jon Keller tells us about the art of moderating debates

On the brand-new “What Works” podcast, I talk with Jon Keller, who has been explaining Massachusetts politics to Boston broadcast audiences for nearly half a century. Co-host Ellen Clegg couldn’t make it on air for this episode, but she handled the editing and will be back soon.

Jon returned to WBZ-TV just in time to cover a contentious governor’s election. He brought his trademark quick thinking and level-headed approach to the recent debate between Democratic incumbent Maura Healey and her Republican challenger, Mike Minogue. Jon was a colleague of mine at The Boston Phoenix, where he wrote a political column. His “Keller @ Large” show remains one of the longest-running political franchises in local television.

Boston magazine twice named him “Best TV Political Analyst,” and he’s won a boatload of New England Emmys. In the Jurassic era, Jon wrote an opinion column for Ellen at The Boston Globe, and today he writes a column for the MASSterlist political newsletter.

Jon has also been caught in the Paramount media swirl as well. WBZ-TV laid him off in October 2025 as part of Paramount’s cuts, but WBZ brought him back as a special contributor in March of this year.

I’ve got a Quick Take about turmoil at The Spokesman-Review in Spokane, Washington. Executive editor Rob Curley, who’s leading an effort to take the paper nonprofit, was placed on administrative leave recently for unspecified inappropriate behavior. Now a deeply reported article by two nonprofit news outlets tells devastating story about what went wrong.

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