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Updated: Feb 11, 2020

By Chris

The Sydney Hobart is a highly addictive ocean race, do it once and you’re "hooked" for life. You get a “rush” or “high” when participating. It's like an addiction, you can’t get enough. Stop for a while you become “restlessness”, “agitated,” or “frustrated”.

It's a game where podiums are elusive, no matter how good you are or how much you spend. A game where some win disproportionately. A game where luck plays a major role creating drama, it's like a game of chance played on a vast ocean racetrack.

What if we treated ocean racing like a game of chance, say poker. Would this give us an edge in the S2H race?

In poker, each player has information from their own cards and what they can infer from competitors. Success relies on exceptional reasoning about hidden information, picking the best actions and ensuring that your strategy remains unpredictable.

Knowing how to subtly bluff and how not to reveal your information is critical. Giving away your future actions gives others an advantage.

In poker, there are 3 things that you need to improve your chances: luck, skill and seeing hidden information.

These things are also what you need to improve the odds in winning the S2H.

Most racing teams have skilled crews and very fast yachts, but few have the skill to see ‘hidden information’ and even fewer act on it.

Because of these three factors (luck, skill and hidden information), rational well-thought-out decisions could fail - while poor decisions may succeed. Confusing? It does seem strange, or counter-intuitive, that the best race teams aren’t necessarily those highest placed, (they may have been really lucky), but rather those race teams with the best decision-making system and judgment.

Just like in poker, there are bad poker players who make bizarre decisions who somehow pull off a massive win - they got lucky. Doing a "Bradbury" doesn't make you a serious champ but winners are grinners.

Watching from the distant shore, good or poor racing decisions tend to look the same. It’s almost impossible to know who makes good decisions from those that make bad decisions.


There are many people who go to casinos to play blackjack and have lots of fun, it’s the same in ocean yacht racing.

These ‘punters’ lose money without knowing the first thing about playing the game. They depend on their “gut feel”. But there are strategies you can learn in blackjack that will improve your outcomes. The S2H is no different, there are things you can do to improve your odds at winning this yacht race.

Skilled blackjack players know when to "hit" or "stay" by following a well-defined "strategy". Some very skilled players are banned by casinos because they win too much.

Successful skippers tend to use a "decision system" learned through many years of racing to enhance their chances of winning. They don’t rely on their “gut-feel”, but on ‘pattern matching’ observations that they have experienced in previous races.

There is no doubt that the S2H, or any major ocean race, is a game of skill. Over many races an inferior racing team, with "knuckleheads" on-board, can’t expect to be above-average finishers.

But because the S2H has elements of chance – top-notch skill doesn't win out in all races. But over many races, a team with superior skills will overcome the adversity of bad luck. The odds are with them.

In any single race, being lucky beats skill, money and a fast boat. It can be indistinguishable from skill unless you are on all yachts watching the decisions being made and implemented.

During an S2H race aside from skill (which most teams have), there are two things that determine how your race turns out: luck and the quality of your team's decision about an unsure future.

A good race team is in harmony with “not knowing” things like where the good wind, shifts, currents and holes will be for sure. Like a poker pro, they embrace this uncertainty and try to figure out how unsure they are, making their best guess at the chances that different outcomes could occur. Improving decision quality on the boat is about increasing the odds of good outcomes, it's not about guaranteeing them.


In poker, hidden information is about the cards your opponent holds, what’s next and working out the strategy of your fellow competitors. And in the S2H hidden information is about future weather, sea-state and your competitors’ strategy to exploit these. It’s about how the environment may unfold and how this impacts both you and your competitors.

Luck in racing is having things happen that can't be predicted, it either helps or works against you or your competitors (they are becalmed while you still have wind, or the wind shuts down as you approach the finish line).

Making high-quality intelligent decisions when future events are shockingly uncertain is the ultimate skill in the S2H. Seeing hidden information helps improve the quality of decision making. But factoring luck into decisions also improves quality.

Likewise, the ability to intelligently grasp and act-on hidden information is a new skill, more important than trimming a sail.

In blackjack, it’s knowing the odds of the next card. In the S2H it's working out the odds of options in a decision, do you follow the pack or become the "lone wolf" going another way, do you hug the coast or go out to catch the stronger winds. Do you sail defensively or 'go all in'.

Decision making using hidden information on a yacht is a process of constantly:

  1. understanding how good your current position compared to others, especially your opponent;

  2. working out which are the gaining and the losing routes are;

  3. understanding what good luck you need or bad luck that could happen to your competitors (and you), and its impact;

  4. making a decision, even when it seems odd

What you’re trying to do is constantly is determine yours and your competitors’ odds in a race and how an action or luck could change the odds.

It isn't about going fast. Success in racing goes to those with the ability to identify superior routes, theirs and their competitors. The goal is to find situations where the odds are generous to one side or the other. It’s like seeing around corners or having x-ray vision.

While considering options the attractiveness of each option is determined by potential gain, the ratio of the potential payoffs (in distance and time) to the amount risked, and what we perceive to be the chance of gaining versus falling behind. (the opportunity cost)

All this is a judgement call, good decisions come from remembering similar patterns in the past, this is why experience matters. The importance of maximising gains and minimising losses against your competitors is the key objective in an ocean race.

You should make big bets when you have a potential big edge and small bets (sail defensively) when you have less of an edge - knowing which is which separates champions from others.

Skilled ocean racers, like skilled poker players, know when the world offers them a gift - they bet big without when they have the odds. And play a conservative game when they don't..

In a race, everyone makes lots of gaining and losing decisions. But the ability to judge the best options should produce more “gainers” than “losers” compared to your competitors. The more ‘gainers’ and the least ‘losers’ you make (compared to all the rest) improves the chances of winning - provided you've raced your really yacht well.

The size of your bet should take into account both the probability you are correct about who’s going to gain and the lopsidedness of the potential payout. A disproportional payout is what you look for. But most people tend to ignore or over- or underestimate probability in decision making.

As Oscar Wilde once said “I can resist everything except temptation.”

A word of warning - many have come unstuck by overindulging in their ‘sure thing’. The ‘sure thing’ is exceptionally rare and very sensitive to changes in wind assumptions. The issue for many skippers is how to properly size an opportunity when they believe they have identified a ‘sure winner’.

Like in poker - you don’t get many great hands, so when you do, you have to be sure to take maximum advantage and go all in. And the last thing you want to do is reveal what you have. Others are watching you closely.

Another thing about hidden information, it can be undone because you let your emotions take over. Hope, emotion and optimism are the gambler’s enemies.

Overcoming emotion and biases, human failings, can cause gamblers to overstay a hand hoping of getting that lucky card, they bet way too much when hurting from a losing streak.

In the S2H it’s no different. Have a few cruel things happen some skippers start to lose objectivity taking larger, senseless risks. How many times do you see the novice break ranks, rolling the dice, splitting from the pack, then paying dearly because they made a very risky call?

On the other hand the opposite can happen after a bad call, a bias to the aversion to risk. To be successful in the S2H you must be able to properly measure the opportunity cost and not be anchored to your previous decisions due to our inbuilt bias to avoid losses.

Loss aversion is the bias to prefer avoiding losses to obtaining gains. This can lead to poor and irrational decisions, where skippers refuse to change.

All past decisions are sunk, not-reversible and a decision to continue on the existing route must always be measured against its opportunity cost.


John Illingworth

In the first S2H, in 1945, skippers like John Illingworth, had little ability to see the hidden information. They relied on their skills and being lucky. They were limited to their own resources and capabilities.

Fast forward today, with on-water internet access, AIS, access to real-time gridded weather data and navigation routing software - all skippers have the ability to see hidden information. Those that understand this edge and how to use it improve their winning odds. It's clear the top yachts do. (See a list of those who do). Navigators like Will Oxley have mastered the art.

The nature of the S2H has changed because of innovation and technology - not just designs, carbon, sails or foils. The race has gotten 67 hours faster since 1945.

Skippers no longer rely on the ancient sailor skills in chart plotting, reading a compass and log, or taking astronomical sights – a cheap GPS and routing software can do all this for them.

Some yachts have better skills in seeing around corners because they understand and embrace the three factors of winning: luck, skill and seeing hidden information.


What superpower would you love to have to win a yacht race? A conversation over a beer might have sailors choosing invisibility, mind-reading or foreseeing the future. Interestingly, all these powers are available to skippers.

These super powers come from awesome technology innovations. Choosing a superpower for personal gain is just about price and how far are you willing to go.


Superpower 1, Gridded weather data are forecasts (for wind, pressure and currents) for every square km along the race track that is projected ( from now to 16 days, or so), in half-hourly increments (sometimes 10 minutes). Gridded weather is produced by organisations with vast resources and massive computing infrastructure. Access to the best and most valuable gridded weather is expensive and the exclusive domain of top-notch teams.

The ability to see currents that are far away is also available in grid format. You can even see it in colour via IMOS.

Gridded weather becomes potent when combined with navigation routing software.


Want to be James Bond? Use put a tracker on your competitor. See everywhere they go - how fast and which way.

Superpower 2, AIS is used to provide access to hidden information about conditions and competitors. And yes it's a major safety improvement so all races insist on it.

It’s an automatic tracking system that provides unique identification of yachts and their position, course, and speed. A skipper can use AIS to see how yachts on different parts of the race track are performing. Do you go out further around the next corner for more wind increasing distance or sail right up to the cliffs reducing distance?

AIS a great tool for seeing yachts beyond the horizon and where they are heading. It can also be used to monitor a forecast storm front, by observing the broken sailing tracks of yachts ahead of you, or behind you. This can be very valuable in avoiding wind holes, avoiding damage or retirement and finding wind.

The best part, it's mandatory in many ocean races.

Trackers. Almost every major race uses satellite trackers, like Yellow Brick trackers, which track a yacht's position, SOG, and COG. This data is provided to race organisers who make it available in many ways. Some providers provide direct access to yacht data for specific tactical navigation software, like expedition ( for example). These trackers have a long latency (delay) as they usually transmit back every 15 minutes, or so, to conserve battery life. Whereas AIS transmission is closer to real-time. Some yachts seem to have "technical issues" with their trackers, their trackers mysteriously turn-off, then mysteriously come back on-line.


Superpower 3 - No going dark is not getting angry or a good tan. A well known trick that some skippers like to do is to go dark (‘turn-off’ their AIS) in strategic parts of their race. Like around Tasman island or when they execute a risky manoeuvre, pick-up wind or a favourable current and don't want competitors to know until the last possible moment. While this defeats the use of AIS for safety - it does give an unfair edge and is almost impossible to prove. AIS can be software controlled so it only receives and doesn't transmit when desired by an operator.


A good example was Black Jack owner, Peter Harburg, he criticised Wild Oats XI for allegedly turning off their AIS before making a tactical “buffalo girls” (sail around the outside) manoeuvre that won them line honours in the 2018 Rolex Sydney Hobart. The protest against Wild Oats by the Race Committee was invalid, because it should have been lodged by a competitor.


AIS is mandatory in sailing instructions but voluntary in practice. The Master/Skipper must choose to 'enable' the transmission. Also, since AIS is a one-way radio signal it cannot be checked that its active ("pinged") remotely.

Effectively, the yacht vanishes when AIS is disabled, reappearing some time later, sometimes a few hours from its last known location. Proving deliberate "go dark" is frustrating for race officials because many AIS transmission "gaps" are not deliberate in the wild. They can be caused by: bad weather conditions, signal collision due to overcrowded areas, or poor coverage (repeaters).


Superpower 4, In the past being a navigator was profession requiring years of study. Today software does the heavy lifting. Today you need to be a geek who loves sailing.

Tactical and navigation routing software, the best example is expedition, takes a yacht's polars ( how a yacht performs in various wind and angles), its available sail wardrobe, gridded weather and performs millions upon millions of complex calculations to compute many routing options based on current position and time. It gives you superpowers.

This can be done with sensitivities to see the impact of slight changes in wind angle, wind speed and timing of wind changes. The results, available in seconds, provide lots of route options and insights. Doing this by hand is impossible, doing it continuously on your yacht's onboard computer is a walk in the park.

This optimal routing can also be calculated for the whole fleet, or specific competitors using their own yacht’s polars, tracker and AIS information transmitted.

This gives the skipper access to hidden information of what are the likely routes his competitors may take. It’s like playing poker and seeing your competitors cards and knowing their strategy. It also allows the skipper to run through what-if scenarios to expose the risks and distill the best route.

Skippers with this routing information are able to use their experience and skills to decide on the best options. They can use this information so assess if a competitor is doing something smart, taking a very big risk, or doing something really dumb. Do they know something that we don't or can their course verify a theory or a hunch?

You are at a massive disadvantage if you are not running expedition in a race.


Ocean races now are effectively marathon match races where you can’t let your opposition gain any advantage. This shouldn't be confused with defensive sailing.

The risk of splitting with the fleet is widely misunderstood. You should split when the odds are in your favour. Blindly following the fleet without knowing why isn't a winning strategy - it's groupthink.

Groupthink describes gaining comfort in something because many other people believe (or do) the same. To be successful in the S2H, you must be able to analyse and think independently.

You should not find any comfort when other yachts are doing the "same" thing or that all your crew agree with you. At the end of the day, you will be right or wrong because of your analysis and judgement is either right or wrong. But you can also be lucky !

Avoid the pitfalls of the groupthink, be a contrarian, have no hesitation in thinking of taking ‘the route with no yachts’ if that is what your analysis concludes.


To exploit emergent hidden information, skippers, masters and navigators play a vital role in a race. Their skills are about presenting hidden information in a way that the crew can debate and consider. The idea is to be proactive in your decision-making rather than reactive.

There are processes and team organisation structures you can use on a modern yacht to distil the “best” decisions and take action using emergent hidden information.

Having two navigators debating analysis is better than a single navigator debating with themselves.

Fast, highly skilled sailing teams must not only need to see around corners using hidden information.
More importantly, they must take the right actions, quickly. The importance of maximising gains and minimising losses against competitors is critical. Just knowing something doesn't automatically translate to gains. You need to act on it.

The right team structure and decision-making process are needed to deal with emergent hidden information quickly.

This is done through a process that discovers hidden information that systematically converts hunches and assumptions into knowledge as the race unfolds. When new information is uncovered, it's incorporated into the evolving racing plan through a well-followed decision-making system that involves all crew.

The more crew that understand the "black art" of hidden information the more powerful the team.

Winning moves are discovered as the race develops and it can come from anywhere on the yacht. Not just the Skipper or "brains-trust".

Seeing hidden information isn't enough. The key is that race teams need to act in the face of this new information and uncertainty. The drivers of this action are not the skipper, or the master. The driver should be the “system” and the crew.

Most often, those with real insights, are usually the crew who see glimpses of what is really going on.

The role of the skipper, or master, is often more about providing time and space for those insights to be heard, identifying which information is significant, and encouraging action using this new insight.



An example of insights discovered by crew without superpowers, just experience.

As context, the conventual wisdom, from old salts, is never cut across near John Garrow Shoal to the finish line in the Sydney to Hobart race. They say - anywhere near John Garrow the wind usually drops away, as it has for countless sailors many times. It is a painful feeling to be sat becalmed abeam of John Garrow Light, just a few miles from the finish line hearing the sound of sailors partying onshore.

During a S2H race we were duelling with a yacht up the Derwent River, they were nipping at our heels from near Iron Pot, and gaining. This yacht previously won the S2H, on handicap, and it also had a well-known sailor as its master ( who later went on to win two S2H races themselves ).

Somewhere near Chinaman’s Bay, our competitor was about to pass us, they hoisted a small kite to sail "hot". And this tactic worked - they got faster. One of our crew raised the idea of cutting across John Garrow as an option. As a team, we seriously discussed this option - while we were in a fierce arm wrestle. We all agreed that it was a winning move, the pay-off was greater than the risk. We actioned the manoeuvre - but didn't want to telegraph what we were about to do.

So, we waited for the competing yacht to pass us; we then veered left cutting the corner, while they continued to straight ahead . We hoisted the biggest kite we had; and with a perfect wind angle to the finish line - we picked up speed. The other yacht watched us in disbelief at first. And as we made better VMG towards the finish line, they decided to follow us take the John Garrow shortcut. They were stuck with an smallish kite and no time to change it, doing so would lose even more distance to us, they played the wrong hand. We crossed the line beating them. It was a very satisfying moment.

Our team structure was designed for crew input from anywhere, we discussed the options and risks. This was all done while still continuing to race the yacht at its best. I suspect that their team structure was the top-down old school where the master was god.


Changing the game plan in a race is often difficult and complicated.

Most of the crew need to believe that if no action is taken now, they will fall in the standings, lose an opportunity and may even waste a race. In a race, you constantly have to adapt the plan and understand the implications.

To be a winning yacht in the S2H you need to get away from the command-and-control mindset. Masters and skippers need to stop pretending that they know all the answers.

In the S2H, where luck plays a major role, it’s a highly dynamic, uncertain and fluid environment (no pun intended), no-one sailor has all the answers. The collective mind and wisdom is powerful.

The job of the modern yacht race leader is to articulate and point out the critical uncertainties, doubts and consequences. And encourage debate how you might gain some insight about them. Arguing about who's right/wrong is just time-wasting leading to heartbreak, frustration and just slows the boat down.

Putting together the yacht and team is one part of the puzzle. Funding is the other.

The owner needs to work on the sponsorship proposition while building both the team and yacht’s reputation. This needs to be integrated with social media and the generation of original content like images, footage and stories. For more on putting together a team and sponsorship read this post " OWN A YACHT RACE TEAM, FOR LOVE OR MONEY?"

Seeing hidden information is not the biggest challenge today because technology provides an edge to do that. It’s all about seeing the consequences of this hidden information that provides an advantage.

Thinking through the costs and payoffs of different options and developing judgement when faced with these options.


In short yes and no.

The racing rules, rule 41(c) “OUTSIDE HELP”, apples to using information. Essentially, part of the rule says:

A boat shall not receive help from any outside source, except help in the form of information freely available to all boats

Information freely available’ in rule 41(c) is information that is available without monetary cost and that may be easily obtained by all boats in a race. Rule 41(c) is a rule that may be changed for an event provided that the procedure established in the rules is followed.

A good interpretation of this rule can be found in the Sailing Case book, case 120

Past S2H sailing instructions (2019 and before) didn't change rule 41(c), this means outside help rule has always applied in past races.

AIS information is freely available, as all competing yachts in S2H must have their AIS switched on its just there.

Advanced weather data is usually provided by providers on a subscription basis, this is how they make their money. Using such pay-for-use subscription services, like Predictwind or Tidetech, do break rule 41(c) however using free weather information, like NOAA, doesn't.

Many services provide ‘free’ subscription with degraded data resolution/accuracy to allow competitors to use these during a race. How many navigators doing a S2H actually switch over from an excellent high-resolution model to a degraded model by changing their log-in information? If they didn't switch how would the race organisers or anyone know?

On-board software for routing, like expedition, doesn't break the rule 41(c) as it’s not outside assistance.

Most of us just want to play an honest game in an age where cheating is more prevalent than ever. It’s fair to say that in most high profile sports where winning has significance - there are likely to be cheats.

Is S2H (or Yacht Racing in general) somehow different from other sports?

Sailing is self-governing and relies on good-faith by competitors to do the right thing and that they take their punishment (do their penalty turns) if they interfere with another boat. Those cheating should be protested, so they realise they can't get away with breaking the rules.

What are the odds that while racing some yachts use information from outside that is illegal under 41(c)? This can happen knowingly or unknowingly.

Not only does a ‘clean’ skipper need to contend with hidden information they need to deal with the fact others may have access to information banned while racing. This is another issue that needs to be managed by the race-team. It's another factor to be aware of.

My view is that 41(c) should be amended for a race to allow outside information, its just recognising reality and create a level playing field.


In summary, the consistent champion in the S2H has to be able to think at a higher, more complex level than competitors while racing while embracing luck and uncertainty. How good is your route?, how good are your competitors’ routes?, what do they know or worked out that we haven't?, is it working?, is it a wicked mistake? Is it time to take a big risk or not?

  • You have to be able to understand which routes are favoured and their attractiveness and odds;

  • You need a sense for whether your route is a good one and the chance your competition might have a better one;

  • You need the discipline to follow a process and have the wisdom to accept that there are no guarantees, sometimes you’re choosing the least worse option (they are all bad, some less than others);

  • You have to understand the significance of the hidden information you uncover, as well as the impact of information which you don’t have and how luck may change all this;

  • You need to control greed, fear, and despair onboard – avoid taking larger and larger risks for little gain, following a system overcomes this;

  • You have to resist making an unwise bet just because it could enable you to catch up with the competition, it's a long race they will experience unwise bets; and

  • You need the nerve to bet heavily based on what you think you know and have a healthy respect for what you may not know.

If you update your view of the S2H and embrace the new perspective, (that it’s like a game of poker), where there are 3 key things are needed to improve your chances: luck, skill and seeing hidden information - you will make better progress to podiums.

Most racing teams have skilled crew and fast yachts, but few possess the skill to see ‘hidden information’ and this is becoming more important as better innovations emerge, like artificial intelligence.

But seeing hidden information isn't enough. The key is that race teams need to act when they are in possession of new insights.

The drivers of action are not the skipper, nor the master. To be a winning yacht in the S2H you need to get away from the command-and-control mindset. Embrace team working in decision making.

In the S2H, where luck plays a major role; it's a highly dynamic, uncertain and fluid environment, where no one person has all the answers. Masters and skippers need to stop pretending that they know all the answers.

Most often, those with real insights are usually the crew who see glimpses of hidden information into what is going on. The role of the modern skipper, or master, is often more about providing time and space for those insights to be heard, recognising which information is significant, and encouraging action and leadership using this new insight.

The winning moves are discovered as the race happens and it can come from anyone on the yacht.

Embrace the uncertainty and go win.

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