Reply To: Should I drop it or confront him?

It does sound like he doesn’t want you to get this job. Big question to consider: how would you getting this job affect him? You say he seemed hesitant about you applying. This suggests its important for you to explore this question. People at the old company he doesn’t want you associating with? Something he doesn’t want you to know about how/why he departed? He thinks this job will take more time and leave less of your time for him?