Phil has always been a bit naive about things, but he's one of the nicest people I've ever met. He's always been a cheerleader. He was that way with LeMond, Hampsten, Millar, etc... He's also always taken the side of the riders until it was proven through testing or the rider admitted it, but I think that has more to do with his personality. He probably truly worries about offending the riders.
Liggett tries to immortalize every performance, and won't ever take a critical stand unless he personally feels assaulted. I mean... Harry Carey was one of the most loved baseball announcers of all time, and that guy bungled more names than George W. in his alcoholic days. While those who sit and cast a cynical eye towards the sport will tend to not appreciate this, I can say that he has a lot of appeal. My mother is no cycling fan, but loves listening to Phil, and I think that is his charm. Those who expect every commentator to be like Paul Kimmage might not like it, but for a sport that depends on sponsor endorsements for it's survival, it's bad business to sit there and will get you fired. Remember that Al Trautwig disappeared after 2007 when he openly questioned whether any riders of the past decade had been clean.
I think to work for a network like Vs. or any other in which you depend on sponsorships for your success, you have to make the sale. It rubs a lot of the purists the wrong way, but not everyone can watch the Tour online, and they have to sell their product to the masses in order to survive. Remember that OLN once carried all three GTs in splendid coverage back in the day, but when they changed management and the former president, who was a cycling enthusiast, resigned... we lost the great coverage and then we get wrap up shows with Hummy and Bobke at night to dumb it down even further.
The thing about Phil is that he tends to not editorialize about the riders in his commentary. When he's written articles or editorials, as he did back when he was the Int. Editor for CycleSport, you'd be surprised, but that side of him doesn't come out in his commentaries on television.
Sherwin, on the other hand, was one of Lance's best friends back before he had cancer... as the PR man for Motorola