RICH PICKINGS: Best and worst 2008

It's been an extremely difficult year for Australia's wealthiest entrepreneurs. Plunging sharemarkets, collapsing credit markets, the odd scandal and corporate collapse – it's a safe bet that many of our richest people will be feeling a little low over the festive season.

How better to cheer them up than with some awards for the best and worst of 2008 – plus a little bit of crystal ball gazing.

Best deal of the year

Finding an entrepreneur who actually managed to make some money in 2008 was no easy task, but there was one standout: Queensland-based mining investor Ken Talbot. The founder of independent coal company Macarthur Coal has actually had a rough time of it over the last few years after becoming embroiled in a corruption scandal, but his decision to sell out of Macarthur between May and July this year was a masterstroke.

Talbot's decision to sell out pushed Macarthur shares from $9.20 at the start of the year to more than $20 by mid 2008 and he eventually netted around $700 million.

Talbot got out just before the coal market started to crash. By late December, Macarthur's shares had slid to just $2.66. Timing is everything.

Worst deal of the year

John Kinghorn pulled off one of the coups of 2007 when he extracted over $500 million from the float of RAMS Home Loans, just a few months before the company's shares tanked and it was flogged off to Westpac for a pittance. But his decision to invest more than $70 million into Allco – even after it was clear the company was doomed – was an absolute shocker. Yes, we know John was a founder of the company, but that is a high price to pay for being loyal.

Most intriguing entrepreneur of the year

No question here, it has to be Fortescue Metals Group founder Andrew Forrest. Over the course of the last 12 months we watched Forrest become Australia's richest man as his fortune topped $12 billion, and then sunk to under $3 billion after the bottom fell out of the iron ore market. We've seen Twiggy chased by ASIC, targeted by short sellers, become best buddies with James Packer and emerge as one of Australia's greatest ever philanthropists. Whatever becomes of Forrest, he can be truly proud of his leadership in creating the Australian Employment Covenant, which aims to break the welfare cycle by providing more than 50,000 jobs to indigenous Australians.

Biggest scandal of the year

In July Australia's richest man Frank Lowy found himself embroiled in the global tax scandal involving LGT Group, the secretive Liechtenstein bank owned by UBS and the Liechtenstein royal family. The US Senate Committee on Homeland Security and Governmental Affairs has identified the Lowy family as a client of LGT Group and accused the family of sheltering assets from the Australian Tax Office by setting up a foundation in Liechtenstein. The Lowy family denied any wrongdoing, but that didn't stop the committee calling Frank Lowy's son Peter before its inquiry. Peter Lowy invoked the fifth amendment of the US constitution, refusing to answer questions on the grounds that his answers may incriminate.

One to watch in 2009

While many entrepreneurs are on the defensive at present, billionaire property developer Lang Walker is ready to pounce on distressed property assets. He has the cash to back his talk up, too. In 2006, Walker brilliantly picked the top of the market and sold the majority of his property empire for around $1.2 billion. Walker is one of many wealthy entrepreneurs who sold out at the top of the market between 2005 and 2007 – expect these cashed up investors to chase bargains in 2009.