IT may turn out to be the biggest own goal in Barry O'Farrell's 18 months as NSW premier.
Clover Moore-backed independent Alex Greenwich appears most likely to win Saturday's by-election in the plum seat of Sydney, a ballot forced by the so-called 'Get Clover' laws which forced the popular Sydney lord mayor to give up her role as an MP.
When Mr O'Farrell announced the legislation earlier this year to ban MPs from sitting on councils, it inevitably raised questions about which of Ms Moore's two jobs the Liberal Party was after.
Was it after control of the City of Sydney council? Or did it want to snatch back the seat of Sydney, lost to Ms Moore in 1988?
Forced to choose between local government and state politics, Ms Moore last month trounced a field of seven other candidates to win a third term as lord mayor.
But now the Liberal Party looks like having to bear another defeat, with candidate Shayne Mallard trailing the 31-year-old same-sex marriage campaigner Mr Greenwich, according to pundits and bookies.
The ousting of Ms Moore has caused nothing but grief for Mr O'Farrell, who was accused of bullying the MP and trampling on the democratic rights of people living in the Sydney electorate.
Even Hollywood star and South Sydney Rabbitohs' owner Russell Crowe came out in defence of the ousted MP, on Wednesday tweeting: "Unbelievable situation in NSW politics that leads to Clover Moore being forced from her rightful place in parliament".
Professor of politics at Sydney University Rodney Smith predicted Mr Greenwich would triumph on Saturday and said if the local government laws were "largely directed at Clover Moore, it was an own goal".
He said the inner Sydney seat, which has taken to Ms Moore's mix of progressive, environmental politics, now had a "strong independent tradition".
"The support that Clover Moore has is strong enough that her aura can be passed on," he said.
"On top of that you have a member of parliament who many would see unfairly removed from parliament. I think it is in some ways an own goal."
ABC election analyst Antony Green said it was "rather hard to tell" who would win the by-election.
"If it was just a matter of the candidates I suspect that the Liberal Party would win, but there will be some festering resentment over the way Clover Moore was forced to resign, and that may assist Greenwich to win," Mr Green said.
"But on the other side of that, Greenwich is not Clover Moore. He doesn't have three decades of working for the local community under his belt. For him to win, it does rely on him taking all of Clover's vote on her recommendation."
Labor, which had no chance of winning the seat, decided not to run to give Mr Greenwich the best chance of victory.
The opposition's 'anybody but the Liberals campaign' will also boost Greens candidate Chris Harris's vote, with his preferences likely to go to Mr Greenwich.
"If Greenwich doesn't hold all of Clover Moore's vote, then it's highly likely that Shayne Mallard will have the highest first-preference vote," Mr Green said.
"But if the Greens get enough votes, and get enough of their people to direct preferences to Greenwich, then Greenwich could win."
Mr Mallard denied encountering any negativity over Ms Moore's exit and predicted the by-election would be so close that a result might not be known on Saturday night.
The former City of Sydney councillor accused Ms Moore of arrogance over her anointing of Mr Greenwich.
"I think she put a candidate out there for her ego, and I think it is rather sad for the candidate," he said.
"I think the constituents are weighing up the merits of the candidates. On merit I stack up ahead of all other candidates in the field."
The openly gay Liberal denied the Sydney electorate was at odds with the conservative government.
"It is an ideal fit for the Liberal Party. It's an ideal fit for a Liberal like me, an inner-city progressive," he said.
"People like me who have a more progressive agenda in the Liberal Party are a great fit for inner-city politics."
However, a confident Mr Greenwich said the seat was not "Liberal, Labor or Greens".
"Sydneysiders want someone who is going to work for them, not a major party, and I'm hopeful that will be reflected when people vote on the weekend," he said.
He said Sydney voters were frustrated over the exit of Ms Moore from state politics.
"It just shows how little Barry O'Farrell knows about Sydneysiders," Mr Greenwich said.
"I think Barry O'Farrell completely underestimated (how politically active they are).
"He obviously thought he'd be able to parachute in a silent backbencher who won't challenge his values.
"But I think the indications are that he has completely misjudged Sydney."
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