Family First senator Bob Day could face a rare High Court injunction preventing him from supporting the Turnbull government's union-busting and same-sex marriage bills after he delayed his resignation to be present for the votes.
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If successful, that unprecedented legal course could be enough to stop the legislation dead, forcing the government to its plan B: a special post-double dissolution joint sitting to get the legislation through.
Senator Day said last week he would resign from the Senate because of the forced liquidation of his businesses, which could leave him personally liable to creditors and could see him lose his family home.
Since then, however, the ultra-conservative senator has signalled his intention to stay in the Senate until at least early 2017, claiming important bills require his input and that to depart now would leave South Australia under-represented.
The past Liberal candidate and former millionaire businessman faces a mountain of personal debts widely expected to render him bankrupt and thus ineligible to sit as an MP. However, that outcome, if it is to occur, could take months of legal wrangling.
Unions campaigning against the restoration of the Howard-era watchdog the Australian Building and Construction Commission (ABCC), and the Registered Organisations bills, are considering their options. A senior strategy meeting has been scheduled for Thursday.
One option on the table is a previously untried High Court injunction preventing Senator Day's attendance in Parliament, given that bankruptcy is grounds for parliamentary disqualification, and the anti-union senator has already announced his resignation because his continued presence would be "untenable".
He said that his creditor liabilities greatly exceeded assets held.
Two senior legal authorities contacted on Wednesday said an injunction was at least arguable, and would turn on whether the High Court regarded the make-up of the Parliament and the eligibility of an MP as "justiciable" – able to be tried within its jurisdiction.
Section 44 (iii) of the constitution states: "Any person who is an undischarged bankrupt or insolvent, shall be incapable of being chosen or of sitting as a senator or a member of the House of Representatives."
Among the arguments to be run would be that any legislation passed could be rendered unsound if the material conditions of bankruptcy had been known to be present at the time, as all but stated voluntarily by the senator.
Despite Family First issuing a media statement on Wednesday suggesting a possible lifeline via a mystery last-minute equity investor, liquidators McGrathNicol have taken full control of his former companies to oversee the disposal of the group's meagre assets to help repay creditors.
Fairfax Media has been told Senator Day has no say "whatsoever" in that process, so the prospect of any white knight investor saving the home-building business as a whole appear remote.
It is understood several buyers are circling for assets following newspaper advertisements, but this is aimed solely at recovering creditors' money, with the secured bank lender first serviced before unsecured investors and then shareholders – including Senator Day – who are way down the list and expected to get nothing.
Labor has revived a Coalition gibe from the bruising Craig Thomson controversy, branding Senator Day's vote a "tainted" one, given his failure to meet contractual obligations to distressed homebuyers and tradespeople.
One of the hundreds of homebuyers hit by the building companies' collapse, expressed enthusiasm for the injunction, arguing that the families are furious, having lived in financial and legal limbo for years with no idea if they would get any relief or be slugged for more money.
In a series of Twitter posts on Wednesday, Mr Day claimed his fledgling party and the state of South Australia would not have adequate representation because a replacement senator couldn't be appointed before the end of the year.
Hanging on to his seat will mean Senator Day continuing to receive his $199,040 annual salary, or about $3800 a week before tax. Senator Day stands to receive at least $45,000 base pay should he delay his resignation until February, when Parliament traditionally resumes.
Since the July 2 federal election, he has taken home more than $30,000 pay despite attending just three out of 15 official sitting days.
Senator Day would be expelled from Parliament if he is declared bankrupt.
He has previously said it "would be untenable to stay in Parliament".
The otherwise low-profile senator is yet to hand his formal resignation to Senate president Stephen Parry.
"Marriage plebiscite legislation, ABCC and our other work is too important to Family First to have a vacant seat for even 1 day in November," Senator Day wrote.
Passage of the industrial relations bills would be a significant political victory for the Turnbull government. Senator Day's vote will be crucial because the government needs nine out of 11 crossbenchers to support the legislation.
Family First officials met in Adelaide on Saturday to discuss the casual vacancy, but the process of picking a replacement is expected to take at least four weeks.
The replacement has to be endorsed by South Australia's Parliament, although Premier Jay Weatherill scoffed at the delay, saying the state parliament could swiftly endorse the party's nominee within a fortnight or less.
