If the two segments are sequential as suggested by the OP, then lots of things are possible.
However, if they are not, if the “Boy, tell me you’re not dumb enough to try this” scene comes somewhere later than the excerpt, then it means that Ebenezar survived the Cornerhounds.
Fifty-fifty, either way. I’m going with the latter.
Personally, I think that Jim is setting up the scene as Eb facing a foe he’s not sure that he can handle, worried about not being able to protect his grandson, Harry—and then Harry deals with the threat himself.
At which point, a flabbergasted Ebenezar turns to Harry and says, bewildered, “How’d you do that, Hoss?”
Because all of the Enemy bad guys seem to know that Harry is Starborn, but none of the good guys.
As far as “Oh, I’m more than dumb enough,” reply, I’m going to take a wild guess that in full, it’s immediately followed by, “...Because Thomas is my brother.”
Because Jim is evil enough to do that, and Priscilla is a good little Sith apprentice.
He also made a comment, WOJ, that major issues like Ebenezar finding out he has another grandson pop up at the worst time. And this certainly seems like a “worst time”.
Oh, I’m also guessing that the “dumb enough” comment is followed in short order by the scene of Harry crawling down what Priscilla (inadvertently, I’m sure) described as a “dumbwaiter” singing the Spider-Man theme.
“Dumb enough”. Dumbwaiter. Because I don’t think that Jim would be capable of resisting a pun like that.