Little is probably best known to Australians as the chairman of the Essendon AFL team.
To New Zealanders he is known as the man who twice got the better of the former Labour government. Over a long takeover process beginning in 2003 Toll paid less than $300 million for New Zealand's national rail operator Tranz Rail, then persuaded the government to spend $100 million upgrading the tracks for Toll to use.
To cap it all off, Little then negotiated a deal to sell the Toll rail business back to the government for $665 million, while retaining its profitable freight forwarding and road transporting operation.
The Tranz Rail deal was but one of a 100 quick-fire acquisitions made by Little after he led a management buyout of the trucking company three decades ago.
Those takeovers took Toll into Asia, and it's this position Japan Post wants to get its hands on. It isn't interested in Toll's fleet of trucks or its warehouses. The state-owned postal giant is buying the expertise of Toll's staff in accessing the Asian market. It has already said it plans to hold on to all of the key executives.
With a shrinking population, Japan doesn't offer any growth opportunity to the soon-to-be-privatised postal service, so Japan Post wants to move into Asia. Ironically, it is paying several billion dollars for an Australian company to help it get there. The deal is a testament to Little's far-sightedness and his tenacity (or pugnaciousness as his detractors might prefer to call it).
Little knew that with a slow-growing population of around 20 million, Australia offered limited growth opportunities. And yet on its doorstep was the most populous and fastest growing region in the world.
But when Little took Toll into Asia eight years ago, investors were sceptical. He stuck with the expansion strategy when the economy slowed and when Asian earnings failed to meet targets.
There's little doubt the deal will go ahead. At about 50 per cent above the current share price, the Japan Post offer is a knockout bid, which the board is already recommending. And the government has already given its support to the deal.
While the deal is a vote of confidence in Australian businesses' expertise in tapping into Asia, it's an indictment on investors and fund managers who undervalue companies which have the foresight to make long-term investments in the region.
Perhaps fund managers will reassess their views of other companies that are moving into Asia, such as ANZ bank and insurer IAG.
CHANGE AT TELSTRA
Australia's largest telco Telstra is also pursuing an Asian expansion strategy, and on Friday appointed the man in charge of that expansion to run the entire company.
Andy Penn will take over from David Thodey in May.
Thodey, who has run the company for five years, has done a good job at Telstra. The shares have more than doubled from all-time lows during his tenure and he has overseen complex negotiations about using Telstra's phone network for the government's National Broadband Network.
But Penn takes over as Singtel-Optus nips at Telstra's heels; embarrassingly, it could overtake the former government owned monopoly as Australia's leading telco provider.
Telstra has big ambitions for Asia. It wants to be earning about a third of its profits and revenue from the region in the next five years.
Telstra's steady flow of predictable and generous dividends makes it a favourite investment for Australia's retirees, who would rather have extra cash instead of profits being used to fund a long-term expansion into Asia.
Let's hope that like other executives leading an expansion to the north Penn can stare down the naysayers and hold the course.
He's seen firsthand the cost of not doing so.
He was chief executive of fund manager AXA Asia Pacific when the company sold off its growing Asian operations to its French parent in a deal that netted him a A$17 million payment. That deal is now seen by some as being short-sighted.
Christopher Niesche is a Sydney-based business journalist He is a former editor of the Business Herald and a former deputy editor of the Australian Financial Review.