He's been doing this since college for already 15 years and has always been quite consistent in his political views afaik. To me he comes as one of the most transparent political commentators out there actually. He always tries to be super accurate and concise when he speaks but never leaving any important details out. One thing he does very well also is that he will always not only say what he thinks but goes ahead and takes care of any possible rebuttals or other points of view you might be thinking of.
Definitely give him a chance.
I like Pakman in smaller doses, but I 100% agree with the above. On your very last point, it should be clear that he does this not to strawman any rebuttals, but to try to paint them in the best possible light before pointing out how wrong they can be. I think this is something not enough people make the effort to do. He also does very good interviews, both with people he agrees with and those he doesn't, but that seems to happen far less often these days.
I really don't like the way he interviewed a woman who was being hounded by gamer gate like he was boogie88 or whatever the hell that guy's name is.
Yes, I recall this. Well, I recall two things; one was that he did an interview like you described where he came off more aggressively contrarian to her points than he should have. The other was that he hounded another woman for an interview (or, more accurately, a "debate" with another guest who was on the other side of that clusterfuck of a topic), and after she refused, he seemed to dig in and send multiple requests on Twitter, which just brought more trolls/harassers along. I think his intentions
may have been good at the time, but it definitely didn't come off that way, especially around the time of that other interview.
That said, I think he's
far better now than he was back then.
(I'm leaving out names, despite knowing exactly who they were, for their benefit)