A total outlay of just under $48,000 laid the seeds of this courtroom confrontation between the 26-year-old Bolton and BrisConnections, the company mandated to build the ambitious 6.7 kilometre toll road. Those listed BrisConnections units were designed to help fund the construction of the road, but are now among the most toxic assets tradeable on Australian markets. Each 0.1¢ stapled unit comes with two $1 instalments to be paid, which means the modest outlay of $500 lumbers a buyer with a $1 million debt. Melbourne housewife Fang He felt the sting of BrisConnections in October. She turned a $32,300 investment into a $65 million nightmare after buying units without investigating what liabilities were owed on them. Countless other Australian families face losing their home after spending just a few hundred dollars on the units. According to his own testimony to the Victorian Supreme Court, Bolton says he knew he was picking up $94 million of debt he did not have the finances to pay. He even contemplated a takeover move for the embattled project, he testified.

Bolton had grand plans, but he has instead been forced into legal combat with BrisConnections, the Queensland Government, investment bank Macquarie Group and construction giant Leighton Holdings. His only perceivable ally in court is a co-underwriter of the float, Deutsche Bank, which is hoping that his punt may cause the next $1 call to be halted, and absolve it from covering the shortfall when retail investors are unable to pay. The other result of Bolton's BrisConnections gamble is unintended, but just as visible. He has shone a light into the most disastrous float in recent history — a deal stitched together by Macquarie, and one of the last major infrastructure deals done before the global financial crisis hit. The capital raising for BrisConnections is very much the famed "Macquarie model" in action, with huge leverage involved. The $4.8 billion project cost is funded by $3.2 billion of debt, and gearing of about 65 per cent. It was also a typical Macquarie model in another way — for putting together one of the worst-performing floats Australia has seen in decades, the investment bank picked up $110 million in lucrative fees. That includes an advisory fee of $56.1 million, a sponsor development fee of $12.5 million, an equity underwriting fee of $28.2 million and a dividend reinvestment plan underwriting fee of $14 million. Macquarie will also be BrisConnections' exclusive financial adviser for a decade.

Before the global meltdown, institutions were queuing for a piece of the action. The consortium that won a 45-year contract to build and operate the tunnel and toll-road project was led by the giant Queensland Investment Corp, which invests the superannuation funds of the state's public servants, and is chaired by ASX director and Future Fund custodian Trevor Rowe. The initial public offering priced shares at $3 each — $1 up front, and two further $1 payments — and was fully subscribed. The structure of partly paid shares is not uncommon, but under this initial offer BrisConnections borrowed against the future instalment payments. A distribution was to be paid to investors from borrowed funds even though the company was not generating revenue. However, cash flow from the project was aimed at eventually paying down the debt over the long term. But the units tanked on the first day of trade, June 30 last year, as institutions became nervous about the global meltdown.

BrisConnections opened at 65¢. By the end of trade, they had dipped to 40¢. Almost 20 per cent of the issued units — about 36 million securities — changed hands in the first 48 hours. Macquarie took a stake in the project equivalent to 18 per cent of the issued units, but sold out soon after the float, dumping 60 million units at a heavy loss. In doing so it dodged a further $120 million of instalment payments. Others followed Macquarie out the door. When BrisConnections listed, just 12 per cent of the units were in the hands of retail investors. That figure now exceeds 80 per cent. As a result, BrisConnections' share price has fallen from from $1 to just 0.1¢, the lowest tradeable price on the ASX. A promised 5.95¢ per share distribution, payable before the second $1 instalment was due, has been slashed to 0.05¢ and postponed until after the next instalment, as part of the board's efforts to save cash. To cap off the mess, half-year results released on February 3 reveal that a decision to hedge interest rates on its loans, using derivatives called interest rate swaps, has caused a $476 million black hole, given the recent round of aggressive interest rate cuts by the Reserve Bank.

In all, the failed float has put the board of BrisConnections and its major backers, Macquarie Group and Leighton Holdings, in a hole. The company has drawn $231 million of its IPO bridging finance facility with Macquarie, and on Monday a further $91 million is drawn on that facility. A $200 million facility with Leightons has almost been exhausted. BrisConnections needs to collect the next $390 million of its instalment payments from unit holders on April 29, or have the co-underwriters pay the shortfall, to pay off its loans. The problem is, many of the unit holders simply don't have that money. Unit holders are claiming they didn't know that BrisConnections' five-letter ASX code, BCSCA, instead of a usual three-letter code, meant it was a partly paid unit with further payments due. That includes Yallambie couple Steven and Violet Csutoros, who bought $600 of units via their CommSec online trading account and now owe $200,000 by April 29. "I just simply clicked and they were mine," Mr Csutoros said. "There should have been a warning, but there was none."

FOR months the board of BrisConnections, and primarily Trevor Rowe and chief executive Raymond Wilson, have searched for an answer to the dilemma. They commissioned Goldman Sachs JBWere to try to find new backers, or create a new financing model, but to no avail. What Rowe and Wilson didn't expect was the arrival of Nick Bolton. Bolton announced to the ASX that his private company Australian Style Investments had become a substantial shareholder on November 24. For weeks, BrisConnections company secretary Tamira Herbst tried to contact Bolton, but with no luck. But even if they did speak, 26-year-old Bolton was not a person Rowe and his team could easily communicate with. There is a substantial cultural chasm between the generation Y internet entrepreneur with a penchant for vintage suits and riding a bicycle inside his office, and hard-nosed pre-baby boomer Rowe and his advisory team.

It took months, but the protagonists finally did get to have a conversation. That was at 3.30pm on February 13, and it was Rowe who picked up the phone. The reason for the call was simple. Bolton had played a card that no one at BrisConnections had expected — he had called for an extraordinary meeting of unit holders to vote on a series of resolutions, which included having BrisConnections' unit trusts wound up. This made Bolton a white knight for BrisConnections' embattled unit holders. Websites and online forums buzzed with hope that the biggest shareholder in the toll-road operator might have found a way out for them. Many had already tried, or suggested online, several methods to avoid making the instalment payments. These included off-market transfers to terminally ill patients, or homeless people, or overseas residents. Csutoros was one who attempted the off-market route, transferring his units to a $2 shelf company that was set up by his accountant. But he soon received a letter threatening legal action from BrisConnections and telling him he still had to pay.

With Bolton threatening to gather the unit holders together for a vote, Rowe needed to act. "I was surprised he took the call," Rowe later told BusinessDay. The pair had four discussions that day, and Rowe agreed to organise a meeting between Bolton and the company's underwriters, Deutsche and Macquarie, in Melbourne. When the meeting went ahead, representatives from Deutsche wanted to know what "value" Bolton wanted. They had anticipated some kind of play, but Bolton did not bite. Instead, he wanted Rowe to use his contacts to set up a meeting with the Queensland Government. For Rowe, that was a step too far and communication with Bolton soon ended. "To this day, I still don't know what he wanted," Rowe told BusinessDay. It is from this moment that negotiations turned into a game of brinkmanship that led the parties to court.

After failing to negotiate a deal with underwriters, Bolton issued a second notice of meeting, this time with a series of cascading resolutions — including a vote to remove the BrisConnections board as manager of the trusts. BrisConnections then started legal action, seeking orders in the Victorian Supreme Court to have Australian Style wound up, and the proposed EGM abandoned because it had been improperly called by Bolton. In response, Bolton started to increase his holding — and offered to take units off the hands of holders via a deed of gift. Unit holders had to pay Australian Style a $1305 administration fee, but it meant they were free from paying the calls on their units. Then, during discovery, came the biggest bombshell of all. Bolton announced that he had an existing put option agreement with John Howard Williams, friend and business partner of his father, John Bolton. It allowed him to transfer his entire BrisConnections holding, which was by now approaching 77 million units.

By the time he walked into court on St Patrick's Day, Bolton and his own legal team faced 30-odd rival lawyers in court. In front of Bolton sat the counsel for BrisConnections, led by Joseph Santamaria, QC, and barrister Phillip Crutchfield, and instructed by law firm Corrs Chambers Westgarth. To Bolton's left sat counsel for Macquarie Group, and next to them lawyers for the state of Queensland. To Bolton's right sat the representatives of Leighton Holdings. All wanted to make submissions to the court. At Bolton's very right sat counsel for Deutsche Bank — maybe his only corporate ally in this case. Indeed, there were so many lawyers that a company put together to solve a traffic jam in Brisbane had merely created one on the street outside Melbourne's old High Court building, as juniors pushing document trolleys queued to get into court. The disaster that is BrisConnections does not start with, or end with, Nicholas Bolton, but his entry in the story has been remarkable. Bolton testified that his purchase of BrisConnections shares was part of a grand scheme to make a takeover bid for the toll-road builder.

Indeed, a strategy document emailed by Bolton to Ernst & Young, ANZ and Deloitte detailed a plan to increase his holding in BrisConnections up to 49.9 per cent. Bolton was seeking an adviser for the detail, but none was forthcoming. The first day of the trial ended without Bolton having to take the stand, and when he did he appeared nervous and couldn't open the door to get into the dock. Eventually he swore an oath, leaned on one elbow, and looked both Justice Robson and barrister Phillip Crutchfield in the eye when he answered their questions. Bolton was cross-examined by Crutchfield over three days. He testified that he entered into a verbal put option agreement with Williams, his father's best friend, on November 18 last year, in a meeting over a glass of red wine at the Melbourne Wine Room. For an upfront premium of $12,100, Williams agreed to sign a deed to take up to 77 million BrisConnections units from him at 0.1¢ each. A two-week hunt for Williams by BrisConnections's lawyers had failed to track him down. They did hear his voice on an answering machine at his home in Brighton, but he had since left the address.

Williams did finally appear in court, walking in at 4pm last Friday afternoon, to the surprise of all but Bolton's lawyers. He denied he had been avoiding being served, testified that he had known John Bolton since 1951, they were great mates and, yes, he had agreed to the put option with Nick. According to the two men, the final written version of the put option deed was signed in the living room of the home of John and Dayle Bolton, Nick's parents, on March 7, just days before the court case was was to begin. But under cross-examination by Crutchfield, some testimony about the dates of meetings, and who was present, varied and changed. Santamaria, for BrisConnections, represented the put option as a "sham" and part of an "exit strategy" designed to send millions of dollars of liabilities "to the bottom of Port Philip Bay". Justice Robson expressed his own view. "What person in their right mind would pay $70,000 for the benefit of incurring bankruptcy?" he said. Throughout his testimony Bolton was selective with his language. He would say what was "an intention" for his BrisConnections holding, but never revealed what was "the intention". But there is little doubt that his intention now is to have BrisConnections wound up.

Late yesterday, submissions in the case were finally heard and Justice Robson will now consider the facts; but he also seems to be aware of a bigger issue — who is looking out for the interests of unit holders? In the words of Justice Robson, these are people in "a very difficult situation" due to the very entity — BrisConnections — that is supposed to be representing their interests. Hugh McLernon, managing director of litigation funding firm IMF Australia, has agreed to pay for a senior counsel to represent several unit holders in the matter next week. IMF successfully bankrolled a class action against Sons of Gwalia in 2003, and has recently been involved in litigation surrounding Opes Prime and Firepower Australia. Loading

Next week, when Bolton, who appeared as a white knight for unit holders takes his favourite position in the middle of court, he might just have a white knight of his own.