Like most people, I don't feel sorry for Tom Flanagan. He was the author of his own demise and given his ego and big mouth, the only surprise is how long it took him to self-destruct.
Flanagan's self-destruction seems to me to be a microcosm of how the current generation of rightwingers in Canada are gradually cutting their own throats. As usually happens, these politicos have been riding a wave for too long now and if scandal or incompetence doesn't get them then they get themselves as a result of typical arrogance and over-confidence.
But while over-confidence of some politicos seem to grow out of the the comfort of power, the current cohort of Canadian conservatives are prone to self-destruction because they are inherently convinced of their own rightness and wisdom. While my experience is that the left has, if anything, been too self-reflective over the years, and "liberals" are, because they inherently occupy the centre of the political spectrum, always waffling back and forth within an admittedly narrow spectrum, the modern conservatives are dangerously convinced that they can do no wrong. And when circumstance proves beyond a shadow of a doubt that they are, indeed, wrong, they simply lie about it or blame someone else. [It sort of reminds me of that old academic story of an idea's development (I can't remember off-hand who originally said it), that a new ideas goes through three stages - first people attack it as being beyond the pale, then the critics admit that it is true but is prosaic and self-evident anyway, then the critics admit that it is true and that they thought of it first.]
Anyway, I have been familiar with Tom Flanagan for a long time and I even audited a few of his classes at the U of C back in the early 90s. I have always found him to be an arrogant wing-nut, a man who is often wrong but never in doubt. He is a racist blowhard whose political theories verge on laughable (if they weren't so dangerous) and he has never been reluctant to share his opinions. These elements of his personality made Flanagan's fall inevitable. Anyone who is that foolish but convinced of his own wisdom that has regular access to an audience, is going to eventually over-reach himself. And by addressing what is, arguably, the most sensitive issue in society, Flanagan was bound to orchestrate his own demise. Ironically, it was, typically, not really the issue that brought him down but his inability to speak about the subtleties of an issue that destroyed him. Having sat in classes with Flanagan when he was twenty years younger and surprisingly a little more cautious about how he said things, my experience suggests that, if one were being generous, we might suspect that what he really wanted to say was probably lost in his typically rightwing glibness. At the heart of Flanagan's discourse was, perhaps, the legal question of the efficacy, expedience, and import of prosecuting people who consume illegal material verses those who are actually involved in the production of illegality. One might argue that it is not unlike the question of dealing with those who consume an illegal product like, say, heroin versus dealing with those who produce it an distribute it. Now, no matter how sensitive an issue is one might need to address this basic legal question, particularly in circumstances of limited legal resources. But it would be impossible for someone as glib and impertinent as Flanagan to actually discuss such an issue. Rather, Flanagan always has a knee-jerk, extremist reaction to any issue. Flanagan never actually wants to discuss an issue, rather he just wants to pontificat as loud as he can to anyone who will listen.
In other words Flanagan doesn't know when to properly tailor his discorse or just keep his mouth shut. And in the end this is why Flanagan split with Harper. If Harper learned anything during his time in public life it is to say as little as possible and even if one has controversial (some might say offensive) opinions, keep them on the DL. And this is why Harper has always jettisoned political alies who he can't control, and also why his government is a grand exercise in keeping everyone around him quiet. And even those close to Harper who are regularly in the media spotlight are continually coached and controlled concerning government message.
Flanagan fell from grace because he is a man full of deeply offensive opinions who is convinced his is a scholar and a genius. It was inevitable that he would shoot his mouth off in a way that would undermine any authority he may have had. Other Harper allies like Brazeau and Duffy are similarly obsessed with their own perceived wisdom and authority. Meanwhile, other allies are just headed to jail.
If Harper has learned how to keep quiet himself, the offensiveness of his opinions and the opinions of his alies eventually slips through the cracks with catastrophic results. Today Tom Flanagan is rightly suffering from an appropriate backlash to a lifetime of offensive opinions. And as the screws come gradually looser on Harper's political machine, it won't be long until the whole generation of modern Canadian conservatives is similarly in the public dog-house.