Mick Foley said in his books that it's much better to build someone up before delivering that crushing insult. Much more effective than constant insults.
So maybe the technique is to be all "Lee, Lee, don't listen to the trolls. You're a great reporter", "I really enjoyed your exclusive last Wednesday" and "I'm surprised the nationals haven't picked you up yet". Gain his trust before crushing him with "Perhaps its because you're shit at your job and a condescending wanker". That'll hurt him.