When we elect someone to public office, we are deciding whose judgment we trust, who will listen when we disagree, and who will remember why we sent them there in the first place.
I have known Jill Oberlander for many years, and I have campaigned for her more than once. Jill is the person you want in the room when a hard decision has to be made. She does her homework. She listens. She asks questions (lots of them) because she wants to understand the details before she reaches a conclusion. And she isn’t afraid to question an assumption, even one that has gone unchallenged for years.
Governing is rarely as simple as campaign rhetoric makes it sound. Projects run into obstacles, priorities shift, and what one neighborhood needs is not always what the next one needs. Good leaders sort through all of it, make a decision, and then explain that decision honestly. Jill has been doing exactly that for years.
She served Greenwich as the first Democratic chair of the Board of Estimate and Taxation, then went on to serve on the Board of Selectmen and the Representative Town Meeting. That experience gave her something no one can manufacture on the campaign trail: a real understanding of how go...