But he's finally come a cropper. This week he picked the wrong target - a woman.

The once big-spending, well-connected master of the universe is now out of a job and he's sparked a heated and polarising debate.

The debate centres on whether he has been turfed as a result of sexism or because the person he publicly lambasted was the incoming chief financial officer of banking giant ANZ.

Gaining notoriety

Here is a taste of what Aitken had to say about the woman's appointment in the note to his big fund manager clients.

"ANZ - that new CFO (chief financial officer) has to be one of the dumber appointments I have seen...another reason not to own this stock. Sell ANZ," he opined in the fateful note.

The CFO in question is Michelle Jablko, a former investment banker.

It's fair to say that the investment banking pool is not traditionally the spot from which the big four trading banks have sourced their chief financial officers.

Aitken, who was head of institutional equities at Bell Potter, went on to tell clients that investment bankers tend to be crap at most things in the very different world of ASX-listed companies.

He goes on to list a couple of exceptions to his rule - and names a couple of successful men.

He then mentions a big deal last year in which Jablko acted as an investment bank adviser.

The deal, a billion dollar takeover by law firm Slater and Gordon, was a disaster.

But the primary blame should be aimed at the Slater and Gordon board. Jablko deserved to cop some flack, but not the lion's share.

Is it sexist?

But is the broker note sexist? And was it sufficiently inappropriate that Aitken should lose his very senior job on the back of it?

ANZ's head of corporate affairs, Paul Edwards, certainly characterised it as sexist in a tweet. Edwards says his tweet got a huge number of likes - almost all from women.

Sexism alive + well in stockbroking? @Bell_Potter Aitkin memo on #ANZ Michelle Jabko CFO appointment @cazzmelbourne pic.twitter.com/NkAu75Ht1D— Paul Edwards (@pgtedwards) May 25, 2016

Aitken's criticism of Jablko's appointment certainly doesn't mention her gender.

But Edwards contends there is a cultural thing - an unconscious bias underpinning Aitken's note. I tend to agree.

Whacking Woolies

But in order to let Aitken have a fair trial-by-media, let's look at some of this other broker-note contributions to the investment community.

"They need a new CEO that isn't a plodder, " Aitken said in a note on Woolworths to clients last year.

"The last few CEOs of Woolworths have been completely uninspiring as retailers in my view. The better CEOs of the past were genuine retailers like Roger Corbett, Paul Simon and Reg Clairs" he said

Aitken said Woolworths also needs to take less advice from consultants, including Cairns' old firm, McKinsey, which played a major role in developing the retailer's latest strategy.

"This company first went off the rails taking far too much advice from these type of players, in my view," Aitken said, citing reports that Woolworths paid $45 million or more to McKinsey last year.

"Whatever the number is, it isn't working!"

Rio rant

Here's some choice quotes from another Aitken note from last year.

"What the f. .k is wrong with these morons," he asked about Rio Tinto management - particularly CEO Sam Walsh.

Aitken was upset that Rio was using its position as the lowest-cost producer of iron ore sold to the key Chinese market to ramp up supply. Its strategy help prices depressed for everyone else selling iron ore.

Aitken said Rio should "tone down the production and the price will rise" - along with the company's share price.

"It just makes no sense whatsoever and is all about a case of big dick syndrome, not profitability."

Tell us what you really think Angus!

Caught in his own bunker

Based on the above examples you might conclude Aitken was an equal opportunity abuser.

But here's a titbit from March 2000 that could colour that conclusion.

It's probably not enough for a conviction, but it's worth repeating.

In an interview with The Australian Financial Review on golf, Aitken was asked who he would most like to play a round of the game with.

His response: "Phil Mickelson, as I am a left-hander and he is a great player and my golfing idol."

The kind of response any keen golfer could relate to.

But then Aitken added this: "His wife is also a former cheerleader who is tremendously good looking."

As a statement, it wasn't so good-looking.

Out the door

But back to the second question of whether Aitken deserved to lose his job for his outburst about Jablko.

From the outside, he already had to be vulnerable, following the bludgeoning he got last year from the corporate regulator ASIC for misuse of confidential client information.