If there was one thing Patrick Brown's advisers never stopped worrying about, it was the women. It was an all-encompassing concern virtually from the outset of his ill-fated leadership of the Ontario Progressive Conservative party.

Today, more than a month after a CTV report alleging sexual misconduct with two women led to Mr. Brown's resignation, and less than a week after he abandoned a questionable bid to get his old job back, details of his doomed three-year tenure as Tory leader continue to emerge. E-mails obtained by The Globe and Mail, and conversations with former advisers and associates, have revealed that the fear of sparking the "wrath of jilted" ex-girlfriends may have compromised decision-making at the highest levels of the Tory party.

Never was that more evident than in the hand-wringing that ensued after details of two nominations held in Ottawa West-Nepean and Hamilton West-Ancaster-Dundas last May became public. In Ottawa West-Nepean, allegations of ballot-box stuffing and membership fraud quickly became widespread.

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The successful candidate in Ottawa-Nepean was of particular interest to the leader's office: Karma Macgregor, the mother of Tamara Macgregor, a former communications director in Mr. Brown's office who had been moved to a policy position. It was no secret that Tamara and Mr. Brown had once dated, and, after she began working in his office, sometimes attended social events together.

Nonetheless, insiders say, Mr. Brown's top advisers, including his chief of staff, Alykhan Velshi, campaign director Andrew Boddington and his deputy, Dan Robertson, all felt strongly that the two nominations had to be revoked because of the appearance of fraud. They felt the situation could haunt the party at election time. The group recommended to the leader that the nominations be held again with stricter monitoring. They drafted statements that Mr. Brown could release about the decision.

Not long after that, on May 19, 2017, the group received an e-mail from Mike Richmond, the party's lawyer and one of Mr. Brown's closest friends. It was copied to Walied Soliman, the high-profile chair of the law firm Norton Rose Fulbright, chair of the election campaign and a friend of Mr. Brown.

The memo expressed concern that overturning the results would lead to calls for the head of then-PC executive director Bob Stanley, who was in charge of the nomination process. Also, Mr. Richmond said he was worried that it might lead other candidates who had lost their nomination battles to demand their results be overturned too.

And then there was a third worry.

"Finally, I think you are underestimating Tamara's reaction," began Mr. Richmond, referring to the former Brown staffer and ex-girlfriend whose mother stood to lose the nomination if the Ottawa-Nepean result was overturned. "We have beaten her up before and she has always taken it like a loyal soldier. But don't assume that past practice will repeat itself."

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He went on: "Tamara has 3 years of texts from PB [Patrick Brown] and the rest of the team. She is also the lead for the story that none of us wants to deal with: the relationship with every female staffer in his office.

"I think it's a terrible idea," Mr. Richmond said of the recommendation to have the results nullified. "If we go down this path, we need to be ready for … the wrath of jilted ex GF/ex staffer." An outcome, Mr. Richmond went on to say, for which they were unprepared.

Mr. Brown's advisers were floored. Not that they all did not have concerns about Mr. Brown's associations with women, including those who worked for him. But they also worried that those concerns would be used as a reason not to do the right thing about the nominations. It was a prime example, they felt, of how proper decision-making was being compromised because of the leader's association and interactions with women.

To no one's surprise, Mr. Brown decided to ignore his advisers and let the nomination stand. Ms. Macgregor remained the candidate until the party overturned the result in February after Mr. Brown resigned. When I reached Mr. Richmond about the e-mail, he said he could not comment because of "solicitor-client privilege." Tamara Macgregor did not respond to text and phone messages from The Globe and Mail.

The e-mail exchange was included in the dossier Mr. Velshi put together on Mr. Brown for the party nomination committee that vetted the prospective candidates for this month's leadership vote – a group that unexpectedly included Mr. Brown himself. The committee green-lit his entry into the race anyway.

The entire matter was just another example of a problem his team had to deal with soon after he took over as party leader.

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The sources say that just a couple of months after Mr. Brown won the leadership in May of 2015, for instance, the advisers learned an Ontario media outlet was digging into his associations with women in his hometown of Barrie. Reporters interviewed bar servers, door men, and women he may have dated, but the investigation produced no stories. Around that time, a group of Mr. Brown's advisers held their first strategy session on how they would handle any allegations of sexual misconduct against their boss.

They talked about what an initial statement would look like and whether it would be followed by a news conference. They began teeing up a lawyer to deal with the situation. They started thinking of women who were not related to Patrick Brown who could vouch for his character. They thought of former employees and colleagues who could do the same.

It was just three months into Mr. Brown's tenure, and his staff was conducting crisis-management scenarios involving the boss and allegations of sexual improprieties.

The nightmare would haunt the group until the bitter end, when it played out in real time and in shocking fashion. It would make Patrick Brown's inner circle recall the words of one of the Tory leader's closest friends and advisers, who once vowed that if a woman ever cost him the election, he would never forgive him.