Though they met briefly in the late 1980s, it was not until April 1997 that Jack Dale began painting and recording his cultural stories with the assistance of Melbourne art entrepreneur and publisher, Neil McLeod. McLeod began his association with artists of the Kimberley during projects in the region as early as 1977 when he first recorded and photographed ceremonies, the manufacture of artefacts and traditional food gathering.

In the late 1990s, Dale participated in a number of group exhibitions at Coo-ee Aboriginal Art, Sydney, as well as Michel Sourgnes Fine Art, Brisbane during 2001 and 2002. These were followed in quick succession by no less than seven solo exhibitions between 2001 and 2006, all organised through Neil McLeod. Amongst the venues were Flinders Lane and Vivien Anderson Gallery in Melbourne, Kintolai Gallery in Adelaide, Coo-ee Gallery in Sydney, and Japingka Gallery in Fremantle.

The works included in these exhibitions were created during workshops conducted at Dale’s home in Derby. Several times each year McLeod would drive from Melbourne to the Kimberley with art materials and equipment for workshops that could last up to a month in duration. His absence from the Kimberley for extended periods enabled the owners of a Perth gallery to claim they had signed Dale to an exclusive contract and to demand that McLeod hand over all of the paintings in his possession to the artist’s ‘new agents'. When the works Dale produced for them proved to be inferior, they insisted that those created for McLeod could not be in the artist’s own hand and called the fraud squad. Confronted by police in Derby, the old man, quite naturally afraid, made no secret about receiving appropriate family assistance. Works were confiscated from his exhibition at Japingka Gallery and sent to anthropologist Kevin Shaw who concluded, as did others who visited Derby to watch Dale paint, that the venerated old artist had no case to answer. The confiscated paintings were returned. The 'exclusive' contract with the Perth Gallery was deemed to be invalid and Dale once more resumed painting for McLeod.

While Dale’s works were freely available in the primary market, his results at auctions were less than auspicious. In 2007, two works sold for what remain the artist's record and third highest price to date. The first of these appeared at Lawson~Menzies in May (Lot 25). Offered with an estimate of $30,000-35,000 this eye-catching 180 x 231 cm image, Male Wandjinas - Baby Dreaming, created just 12 months earlier, sold for $31,200 to a buyer who had already announced his intentions prior to the sale. It was obvious that powerful primary market influences were at play in underpinning the work of an important old artist of whom most collectors were, as yet, largely unaware. At its next sale in November 2007 Lawson~Menzies featured another major work, this time measuring 143 x 199 cm. This canvas, Wandjinas at Iondra 2006 was an even more impressive painting than the former lot and sold above its high estimate for $45,600, the artist’s current record price. As a direct result of these two sales Jack Dale shot to 120th on the most successful artist list. Further success in 2008 when two works sold for $38,400 and $13,200 saw him leap to become the 66th most successful Aboriginal artist of all time. In 2009 strong sales pushed him further to 60th, with a highly impressive average of $20,518. This was all the more remarkable because he had yet to reach the threshold of 20 works offered. In  2010 another seven works appeared at sale pushing over the threshold for the first time. However it was not the most opportune time for it to do so even though three new works entered his top ten sales records. In 2013 and 2014 two fine examples entered his top 10 records but his results have not been nearly as impressive since and his ranking has dropped sharply. He is currently the 100th most successful artist of the movement.

While one would expect that Jack Dale’s rating and position to have continued to rise, they have not done so. His high value works tend to be large, and for this reason, few are offered for public sale. Major paintings sell for $35,000-40,000 in the primary market, as no other artist has portrayed these iconic creator beings on such a scale other than perhaps David Mowaljarli. They are now being shown internationally. As time progresses these paintings are likely to become emblematic of the last artistic outpouring of a generation of genuine characters that embodied the spirit and Aboriginal heritage of the West Kimberley region.