Obi-Wan is also sorry Mandalore lost such a caring leader. Only to have the planet fall into the hands of his old nemesis. He has no idea what became of all of that.

“I’m certain they do. That sounds like the Senator, but I’m certain he hates every moment of it.”

Submitting to a tyrant even if only for appearances and preservation is not something he could see Bail enjoying. Even though it was necessary. But if anyone could pull it off Obi-Wan is certain he could.