It’s a question everyone gets to ponder at some point. What would you do if you won the lottery and were suddenly unconstrained by budget? I have seen many individuals agonise over this and witnessed committed couples get into intense arguments over how their respective lives would be changed by the proverbial ‘golden ticket’.
I generally find though that when ‘the question’ gets asked of a bunch of racing sailors the responses are significantly less contentious. I think this is because, for a racing sailor, the question of what you would do if you suddenly became fabulously rich, actually translates as which boat (or more realistically, boats) would you spend your endless leisure time racing if money were no object.
Having mulled it over on many occasions, I already know in some considerable detail what my plan would be.

First up, I would join the happy band of owner drivers in the 52 Super Series and RC44 Cup. I have spent plenty of time around both of these circuits and I have always secretly pictured myself on the tiller / behind the wheel. If I close my eyes I can picture myself clearly: the Mediterranean glinting off my Kaenon sunglasses, head cocked slightly to the side in concentration, while in front of me a melee of highly paid professionals whirrs into expert action as I bear away smoothly around the top mark with an impressive three length gap ahead of the fiercely chasing pack.

On the subject of the tranche of professional sailors I would need to hire to ensure we are at least in with a shout of winning races from time to time (and maybe even an event or two) my primary selection criteria here would be mostly based on who I felt like I could have the most fun with. I do not want to hire the world’s best tactician only to find they spend the bulk of the regatta in a sulk because I did not get off the line properly or could not hold my lane on the first beat forcing us to tack away and destroy his carefully constructed master plan. The smartest of the pro sailors in the grand prix owner driver classes know all too well that they are hired not just for their sailing prowess but for their understanding that their primary responsibility is to ensure the owner (and his friends) have a good time. Happily for newly minted lottery winners like me there are plenty of them out there to choose from.

For a change of pace from the four-windward/leeward-races-a-day cut and thrust of the TPs and RCs I would also invest some of my new found wealth to involve myself in the J Class. I can almost hear the murmur of approval from you as you read those words. Who would not, if they could comfortably afford it (and in this dream scenario I can, remember), want to own a J Class? I know I am probably preaching to the converted here, but these boats are the very pinnacle of yachting style and powerful elegance. Things of beauty that once seen under full sail can never be forgotten. Taking on the commitment of owning one is not for the faint-hearted and requires deep pockets. But becoming a J Class owner instantly makes you an integral part of the rich history of this class and links you directly with the fleet’s golden years as part of the America’s Cup.

I am not sure if it is de rigueur among J Class owners to sleep on board their boats at regattas, but I definitely would. My crew – a bigger number now but built around the core contingent that race the TP52 and RC44 with me – can sleep ashore somewhere decent (with a gym and all the five star facilities, of course. But myself and my friends – of which I am sure I will have plenty in this little fantasy – will live on board, enjoying sundowners on deck before dinner and great conversation down below. (An author’s note here: I have never actually sailed – or indeed set foot on – a J Class yacht, so all of this preceding paragraph might turn out to be utterly impractical. For now though let’s go along with it.)

My annual sailing schedule should be filling up nicely by now, but I feel I should also include a little local sailing too. I have not given much thought to where I am going to live but it will be somewhere sunny and a location that can deliver a thriving midweek evening racing scene too. My weapon of choice here would be an International Dragon. Once again a thing of beauty – and once again a boat I have never ever sailed. But they look nice on the water, have big fleets, and I have always been a fan of super-close one design racing. No pros in my Dragon crew – this is club racing, after all – which will be strictly reserved for friends and family and introducing nieces and nephews to our glorious sport.

For those rare moments when I want to race alone and relive some of my favourite years of sailing I would invest in a Melges . I probably would not race the Finn but save it for those times when the mood takes you and you just want to get out on the water for a few hours in something fun but challenging.
Every year I would pick a major one design class world championship to put together a campaign for. It would have to be one happening somewhere appealing (they do not always, believe me) and in a class that I would enjoy racing: so Melges 24, J70, ClubSwan 36.

Or actually, now I come to think about it, the new ClubSwan 28. That looks like a great piece of kit. It is fast and reassuringly expensive and I do love a sportsboat where the crew sit facing in – so much more inclusive than having people hanging upside down from the lifelines.
Beyond all this: I would squeeze in a transatlantic race or two on something big and fast – basically whatever is the latest version of Comanche that gets us there quickly and ahead of the fleet.

Nothing that foils, though. The brutal motion on board the latest generation IMOCAs at speed is unpleasant to say the least and an experience I can quite happily do without. That is not to say that I would turn down an offer from the sales team at Baltic Yachts for a test sail aboard their offshore Baltic 111. You never know, I could be persuaded. For the record, I would give serious consideration to an AC40 if that class ever becomes an owner/driver class.

When it comes to superyachts I think chartering is probably the way to go here. I have always been in love with the stunning 65-metre Royal Huisman ketch Aquarius II which I watched race a few years ago at the St. Barths Bucket. I read recently that the husband and wife owners have recently commissioned a replacement so maybe the original is available for charter.

Whatever the boat, I am confident that ‘wealthy-me’ would be a good owner / driver. One that the professionals would appreciate working with. An individual who keeps his mouth shut while racing and takes the guidance he receives from the experts with appreciation. Not someone who hires Olympic medallists, world champions, and America’s Cup winners and then thinks he/she can do better. No one in my crew would be left feeling so frustrated that they write their exorbitant day rate on the palm so they can glance at it from time to time during the race to remind themselves why they are putting up with it all. (True story).
On my boats, the rule would be that we win and lose as a crew – and in either case we enjoy drinks and dinner together each evening after racing. At my expense of course. After all, I am – even if only for the purposes of this story – a fabulously rich owner.
I am off to buy a lottery ticket – the only missing part of my plan.
Justin Chisholm