Michael Freedman's final day as a Hong Kong-based trainer on Saturday, ironically, holds at least the pre-race the promise of being one of his better battles in the brief and difficult war that has been his time at Sha Tin.
He has chances to win multiple races but even if Saturday's meeting comes and goes without fanfare, Freedman's departure has some significance as the Jockey Club looks around for replacement expatriate trainers.
Expatriate trainers have been a big part of Hong Kong racing since its inception in the 19th century, given its history as a colonial settlement.
The British, the Russians, the Australians all plied their trade in Hong Kong in the amateur days and then into the early professional era, even before the concerted drive to lift and broaden the overall standards in racing began in the early 1990s with the recruitment of big names from overseas like Neville Begg, Patrick Biancone, Ivan Allan and David Hayes.
Some made more impact on the Hong Kong scene than others (and in different ways) but Allan and Hayes, in particular, changed the landscape, winning multiple championship titles and more than their share of the big domestic events and driving the successful campaigning of Hong Kong horses overseas at the top level.
Since the turn of the century, though, freshly-imported trainers Tony Millard, David Ferraris, Paul O'Sullivan, David Hall, Andreas Schutz and Richard Gibson have had major race successes but only John Size has been competitive in the championship as well, and he has yet to make any mark with foreign runners. Majors aside, Schutz's time here was disappointing and he, Sean Woods and before them Peter Chapple-Hyam left under the shadow of consistent underperformance.
David Oughton, Ferraris and O'Sullivan have also claimed big wins overseas but advancing the Hong Kong cause on foreign tracks has mostly fallen to John Moore, Caspar Fownes and Tony Cruz - who could all come under the umbrella of "locals" if we take a certain view - with victorious cameos from Michael Chang, Ricky Yiu, Danny Shum and Derek Cruz, all local products.
Moore (left, with Beauty Generation) is nearing retirement, which will leave a big gap in international ambitions, and the bottom line is that expatriate trainers have been having a declining impact. The Jockey Club has found it increasingly difficult to find suitable trainers overseas to set up shop in Hong Kong, despite good prizemoney and an exceptional environment for trainers, who have none of the auxiliary financial and administrative concerns that accompany training racehorses in many countries.
On the flipside, we are seeing impressive starts for local products like Frankie Lor and now Jimmy Ting.
With Freedman electing to return to Australia after little more than a year, regardless of the underlying reasons, there is a message going out now for trainers as it has been for jockeys, that that Hong Kong might not be the promised land any more. The Jockey Club comes to a fork in the road, with two vacancies now, others looming and a query on the options for filling them at the desired level.
The quest to fill one of those slots with a trainer from the northern hemisphere has been a fruitless chase for several years. Race day drug laws in the US compromise potential trainers from there, while promising young British or European trainers get snapped up by big money owners and those who do show interest in Hong Kong either don't have runs on the board or have never trained on a racetrack and work in circumstances so different from Hong Kong that it's hard to be confident that they will adapt.
At least the vacancy left by Freedman has one blessing in that it will likely be filled by another southern hemisphere-based trainer, likely from Australia.
The appeal of Hong Kong seems undiminished but some terrific, keen prospects from there have been overlooked in recent years and some are now out of reach. The next expat to arrive has to be the right all-rounder - a title contender, a big race player, a savvy communicator with an international appetite.
It's a rare mix but our sources say the club has the right person in its sights.