Tic-Tac-Toe, or any other solved game that lets either player force a tie.

Solved games, especially easy ones to remember like tic-tac-toe, can be pretty boring because both players can play their optimal winning strategy regardless of what the opponent does. This means if both players of a game of tic-tac-toe are playing optimally, then it will only ever result in a tie unless somebody gives up.

However, this forced tie is how you beat Death: you're dead and fighting for your life, so you got all the time in the world. Death has places to be, souls to reap, so he has two choices: give up and let you win, or continue playing while the rest of the world enjoys their immortality.

The question itself is not really answerable. Since Death gets to choose which games he is willing to play, we can't achieve a 35% win rate unless Death wants to give us a 35% win rate. Thus we need to work to the motivation of Death. What does death want?

I can't speak for Death here, because Death's motivation isn't in the question's text. However, I can offer you a game which is peculiar enough that it might pique Death's interests.

Here's the game: Death writes two different numbers, one on each of two slips of paper. These can be any real numbers. Death can be as creative as he likes. Death then seals each slip of paper in an envelope so that nobody can see the numbers.

Death then hands you the two envelopes in any order he pleases. You get to open one envelope and look at the number. You must then announce whether that is the larger of the two numbers or the smaller of the two. If you guess correctly, you live.

It sounds like a really boring game. Death is certainly not going to give you a 50% chance of going free like this. But here's the sweetener. I assert that there is a strategy which offers better than 50% odds at this game, and I'll tell Death the strategy if he is willing to play the game fairly.

Think about it. How could you get better than 50% odds of winning that game? When you're ready, the answer is in the spoiler tag below:

To win strictly more than 50% of the time, we need a random number source which is capable of drawing any real number. A Gaussian (normal) distribution will suffice. Since we got Death to agree to play fair, he wont muck with the distribution.


Draw one random number from your source. Open the envelope and compare the number on the slip to your random number. If the number is larger than your random number, announce that the envelope contained the larger of the two numbers. If the number is smaller than your random number, announce that the envelope contained the smaller of the two numbers.

It's truly absurd, but it works. I've run it past mathematicians before, and the consensus is that if you're really careful in your mathematical phrasing of the game, it turns out to just be a really novel nuance, rather than a mindblowing hack. But it works. Rationale is in the spoiler below:

There are three possibilities for how these numbers can be arranged. If your random number happens to be equal or less than the lower number on the slips or equal or greater than the upper number on the slips, then you basically have a 50% chance of this strategy picking the right answer. That's to be expected. However, if your random number is strictly between the two numbers on the slips, then you have a 100% chance of winning. Because there is always a chance of picking a random number which falls into that open interval, no matter how slight, it guarantees that this strategy has a greater than 50% chance. Mind you it might be arbitrarily close to 50% odds, but it will always be greater than 50%.

I think that that's enough of a mind blower that it might get Death to play the game with one person, just to learn the trick. Curiosity can be Death's motivation. Let's just hope you're the first to try it. It won't be so curious the second time!

You can't win.

^{Not even once, not ever.}

By definition, at most one player in a game can have a winning strategy

A winning strategy is a plan for playing a game that means you win no matter what the other person does.

This means that any game that is solved or potentially solvable (such as Chess), Death will always take the role of the side that has the winning strategy and having been around the block a few times, can experience time at an accelerated rate, can conceivably play against himself, and is the smartest person to ever potentially live he is guaranteed to have the winning strategy in any game with open information (chess, checkers, Tick-Tac-Toe). Or at least, can be expected to have a better strategy than you do.

Any game where either player can play for a tie, Death either rejects, or plays you to a tie into eternity. If you change the rules such that you win ties, Death rejects the game outright. Or in the case of Scam School Tick Tac Toe, Death gets to be Brian Brushwood.

In any game involving elements of chance, Death wins. See stipulation #2. This goes for all forms of randomization including laying cards face down on a table, dealing cards to each player, or even as complex as the shuffled order of cards in a Magic deck (this one's easy: Death puts all but one land on the bottom and then orders his deck as he sees fit). It does not matter who shuffles, the size of the collection, or the frequency of shuffles, or "outside" sources of randomness.

In any game that subverts any of the stipulations (such as cooperative games), Death wins on account of rejecting the game outright (think of this as "the game is to pick a game Death won't reject but lose if he plays: Death wins if he rejects the suggestion").

If presented with "Suggest a game. Death loses if he rejects the suggested game, otherwise play the game to its conclusion", as Death rejects the game outright. "...and we're already playing" is cheating. See stipulation #8. Subclause "...and I play as X" or "...and I get to pick a side" Death rejects outright.

Any game you create on the spot will likely contain winning strategies, that Death--given a minute--will uncover that you will be unaware of (or violate a stipulation and be rejected). Any game created prior to dying has the same problem: Death will have already figured out all possible winning strategies and either beat you 100% of the time or reject outright.

Essentially what you're looking for is a game that meets the following criteria:

• It is so complex with interconnected causal relationships that Death is unable to compute a winning strategy or incapable of determining a optimal and suboptimal random results (i.e. if both you and Death have the same deck of cards, Death cannot find two shuffles that offer different odds of winning).


• You, as a mortal, know the winning strategy.

The closest I can come up with is playing a game of Dominion (or a similar game) as while both players start with the same deck of cards, even potentially in the same order, the game's possibility space explodes after the first reshuffle. The problem here is that Death need not control the first, second, third, or even the six shuffle perfectly. He only needs to control the one shuffle that allows him to buy the first Province while also preventing you from doing the same on your next turn. And that is quite doable (all he has to do is arrange your coins in an order that prevents you from ever having more than 7 in hand at one time and I've had this happen in real games).

_{Note: Death can do this by making your deck and his deck play card for card identical even after shuffling. He can either play first or he can follow your plays right up until the critical threshold where buying a Province is possible. In the latter case he doesn't even need know the full rules or figure out how cards interact with each other.}

There are a handful of cards that could upset that balance, but using them would result in one of two scenarios:

• Death rejects (or "randomly" precludes) the setup


• s/Province/That Card (i.e. Death beats you to it)

That or challenging him to a game of "live life all over again." But I have a sneaking suspicion that Death wins that game too...

Predicting the actions of someone you know

If there is no new information from the world of the living in Death's domain, then the personality of someone who is still alive is unknown to Death. Therefore, you must make a wager with Death that if Death offers someone, still alive, a deal, you will predict whether that person will take the offer or not.
For example, Death could offer this person riches or some other reward in return for some sacrifice (say, this person's soul).

In this game, you have the information advantage over Death. While Death has undoubtedly known billions of people in his time, he doesn't know the single person over whom you are wagering.

As long as you know that person well enough, and that this person has the moral character you think he/she does, you should have at least even odds of correctly predicting that person's actions when offered a deal, even if Death does his best to offer the deal in circumstances that favor him.

I'm thinking of a number from 1 to 100. Is it even or odd?

This gives you a 50% chance of winning, regardless of whether you are the thinker of the guesser, assuming death can not read your mind.

To be safe though, use a coin if guessing or a d100 if thinking. He can't influence the outcome as this is not a game of chance.

The key point here is that "Death is too competitive to let anyone win". You're playing for your life, but he apparently doesn't really care about that. He wants the win. It's just a game to him, and given that he has you outmatched in every department he expects to get you beat.

So, let's take a look at the game of Mornington Crescent, made popular on British radio comedy panel show I'm Sorry I Haven't a Clue.

It's a silly game that is played for laughs, but it can have real strategy. While part of the fun of playing is to allude to lots of nonexistent rules and playing styles, the actual gameplay is simple:

• Contestants take it in turns to name stations on the London Underground (or sometimes other places).


• The first player to say "Mornington Crescent" wins.


• A win is considered "better" or even "perfect" if you say "Mornington Crescent" exactly before your opponent was going to say it.

As the players take it in turns, there's a slight advantage in going first. Death could go first, say "Mornington Crescent" and win, but he's competitive. He wants to beat you. He's got a great poker face and is a master of spotting tells, plus he's cleverer than you and has been around a lot longer. An imperfect win - particularly one earned in a way that would allow any fool to get the same result - would not satisfy his competitive nature.

Now the two players have different goals. You don't stand a chance of outsmarting Death or reading him to guess when he'll say "Mornington Crescent", but you don't care about a perfect win. You're thinking about living, not doing best in the game. A weak win would do you fine. All you need to do is to say "Mornington Crescent" without Death spotting your tells - which we know he's good at, but not infallible. This can stack the deck well in your favour.

Winning a game is "easy", the real problem is tricking Death into accepting a game you can win, when Death can reject any game he doesn't like, he must understand the game before making a decision, and he's smarter than you.

Perfect information games won't work: either both can solve it/know the solution and he knows you have a fair chance (so he rejects it), or he can solve it and you can't. An exception would be a game that is solvable but would take Death millions of years to solve (even considering he's VERY smart and he can dilate time a thousandfold), and to which you already know the solution (possibly because you came up with the game yourself). I can't come up with such a game.

Any game where physical reactions intervene in any way is out of the question (or out of the answer) as well: either he is unlimited in that regard, or he isn't and he'll reject the game.

Chance games are excluded as well, since he can alter the odds in his favor.

That leaves us with imperfect information games that seem like they can be perfectly predictable but there is an element of unpredictability, and where the unknowns don't depend on chance at all.

The gambit must be played beforehand, before Death even accepts the game. Meaning, the real game is having Death accept your game, and so the apparently perfect but actually imperfect information must be in the rules themselves.

You can introduce apparent chance, and then take control of the outcome. For example, you can say "I will launch a coin into the air, and you must predict which side will be facing upwards when it touches the ground", then you launch the coin into the air, Death chooses, Death alters odds in his favor, you grab the coin mid-air and place it on the ground with your winning side up.

You can also introduce apparent predictability and transform that into unpredictability. For example, you can say "I will say five numbers between 1 and 1000, and you must predict the 6th number. I guarantee you that a human has 100% chance of knowing the 6th number before I say it." Then you say six numbers, as random as you can. You yourself are a human, and you knew the sixth number before you said it, and this will be true no matter how many times you repeat the game. Sure, Death is SUPER smart, so there is a chance that he figures out a pattern in your numbers that you yourself don't even know, plus the 1/1000 chance he has of guessing the number. However, I would argue that on his first round of this game (and the only one that determines your life), his chances of predicting your pattern are very low, well below the 65% Death win chance threshold for answers to this question.

A third way is to make the game unwinnable for both Death and you. For example, the Tic Tac Toe idea, though Death won't accept that.

And finally, you can prevent Death from killing you by challenging him to a game that will leave him forever unable to do so. For example, challenge him to a game of Starcraft II (a computer RTS) with the rule that until the game is over Death will suffer from all human limitations. Pause the game and murder Death. Careful, this might break reality, but hey, keeping reality unbroken wasn't a requirement for an answer.

Cards Against Humanity - with a twist

I used to play CAH with my friends. To make it more challenging, we created a new rule, called the Invisible [I can't say it in this family-friendly site].

During the czar's turn, they don't receive the white cards from the other players directly. Instead, the players all get their own white cards in a pile and add as many cards from the white stack as needed to fill in the black card's blanks, without looking at those cards' text. Those extra cards belong to the Invisible [can't].

If the czar chooses the Invisible [nope]'s cards, then the awesome point goes to him. This makes it possible for the imaginary N... to win the game (we played until someone had ten points), in which case no single real player wins and nobody has to pay anybody else's tab.

What I only realized a couple minutes ago is that the Invisible [redacted] rule allows CAH to be played by just two people; just add another rule that the Invisible [God we were imature] never wins, and whomever gets to an agreed amount of awesome points first wins.

When it's your turn to be the czar, you'll have a 50% chance to give Death a point. Before you overthink this, while it is true that the Invisible [I'm kinda ashamed now] tends to give completely nonsensical answers, you have no way to tell whether a sensible answer is a fluke and a totally random one is a bluff. Just the same, when Death is the czar he has a 50% chance of rewarding you, and if you pull an Invisible [I am a horrible person] and give your own cards randomly, you don't even need a poker face. Since the Invisible [...] can't win, there are no ties, so your chances to win the game are 50%.

A series of guesses of the number between 1 - 10, where the guessee writes the number down beforehand, with the guesser alternating - best 3/5, or 4/7, or 5/9, with the number of rounds decided beforehand.

The winning score is the lowest sum of the deviations from the correct number.

I don't see why death should have any particular advantage, other than perhaps insight into patterns of numbers picked.

or

rock-paper-scissors.

If death refuses to play those, let him propose games until he suggests one that allows you a ghost of a chance. Otherwise, there is no game at all, you should resign yourself, hold to your dignity, and tell death to pizz off.

Rig a Visual Novel

The explanation will be at the end.

The only way to win this is by suggesting a game that seems fair on the surface, but is secretly rigged in your favor from the outset. The following rules act against you and therefore mean you cannot involve a game with these elements:

• In a game of chance, the dice (or equivalent) fall how Death allows them to.


• If there are unequal roles in the game, Death must be allowed to choose beforehand which he would like to be. (White in Chess, Dealer in card game, etc.)


• Physically, there are no hard limits on Death's strength, speed, or form.


• Death will be the arbiter of any competition, if there is one.


• Death has a better poker face than anyone alive. And he's quite good at recognizing tics.


• The maximum number of opponents he will face in the same game at once is one.

This means games of physical prowess, team games, games of chance, games where either side could have an inherent advantage simply based on role, and games of face-to-face interaction are ALL excluded from the list of viable options. Since we can't expect a pity victory because "Death is too competitive to let anyone win," we have to assume any victory should come from convincing death that the game is fair when really the game was made so that it was rigged in your favor.

• Death has lived thousands of years and played thousands of players.

Then don't play him directly. The only way to play is indirectly.

• There can be no new information from the world of the living in Death's domain.

Then use what exists now for creating the game.

• Death would probably be among the brightest minds to have ever lived, if he ever lived.


• In the space of a minute, Death can experience a thousand minutes.

Then make sure the game is not a game that requires knowledge to win nor rapid mental processing. Make it so that he can't just think his way to the victory.

• Though Death allows the visitor to choose the game, he will reject games at his own discretion.

Make it seem perfectly balanced when in reality it's not. He has no reason to reject something he thinks is fair.

• Death must first understand the rules of the game before he will play that game.

Simple, the rules of a Visual Novel are as follows:

1. Read the story


2. When you get to a choice, select the best choice you can see


3. Try not to get a "dead end" or "bad end"


4. The winner is whoever gets the best ending of the game by the end of their first attempt at playing

There is no reason to refuse this. On the surface, it would seem fair. Both players are working with the same tool for the same end. In Death's mind, the game would be easy for him to win because he can use his immense knowledge and wisdom to determine all the right answers. He can get the best ending no problem.

The trick is, the player needs to make the Visual Novel. Say, "Give me the time to write a visual novel in this space separated from the flow of time. After I've written it, we both play the game. It will be a simple VN where the way to get to the ending is by selecting the right answers to the questions you're asked. At the end, the game will give both players a percentage score based on how well they do. Whoever has the higher score wins. If we tie, for example, if we both manage a 100%, it will be treated as your victory and my defeat. If I have lied to you about the rules, it will be treated as your victory and my defeat."

When writing the game include a "What's your name prompt" where if you give the name of your favorite fictional character, you will get an additional 5%. Make it so that by playing the game, you have to interact with multiple background elements that don't appear to be special and that even if you do so, no matter what you do on the first play-through, you can only ever get up to 95% best ending, based on the fact you would need to do a New Game+ in order to accomplish 100%. Because you would play using that character's name and the game is rigged to max out normally at 95% on the first play-through, Death will be tricked into thinking the odds are slanted in his favor, but really the odds are slanted in your favor. You're not cheating. The rules of the game are the same for both of you. You just happened to know how to slip an unfair advantage past him and never lied about the rules, meaning he can't claim that you cheated because it was all within what was allowable.

I will accept an 'answer' to this question if the victim can have at least a 35% chance of beating the Death, assuming Death is true to form.

You either get a higher score than Death or you don't. 50% chance either way, since you already know everything about the game. Since you know the extra 5% trick, your odds are actually increased. Even if Death does everything after the name right, your odds of winning are much higher than 35%. This just requires that death does not reject your proposition, which you rigged things in his favor (on paper) so that he has no reason to reject the game.

This, as an answer, is honestly "cheezing" the system big time, though. In reality, there is no way an actual "good" answer can be made because Death will reject anything he doesn't think he has the obvious advantage in.

The basic solution to this is actually simple. Choose a game where you always win. You cannot win a game where who wins is a of contest. Nobody cheats Death, nobody beats Death. You will simply lose after wasting lots of stress and effort on it.

I am sure everyone is going "But Death can reject the game at his discretion!" by now. Maybe even started writing a comment about that. But...

The key part of that "rule" and the entire "Death plays a game" concept is "at his discretion". Nobody ever defeats Death unless he chooses to allow it. Never. Nobody.

Maybe some übergods playing outside Deaths direct domain, possibly. But Terry Pratchett actually used that idea and Death won. Basically, anyone arrogant enough to challenge Death has already lost.

So really, the actual game is a red herring to tempt you to arrogance as well as a loop hole for Death to cut some slack when he chooses to do so. I mean, they will be back, he does not need be that strict about it.

As for the actual reason for Death to allow defeat, that obviously would depend on the setting and circumstances.

But some examples, the last two are probably most usable :

Hubris

Some evil people have defeated Death in games. This happens so that they will have the time to regret their "victory", repent, and accept Death. Probably not applicable to protagonists but most common, so included.

Serve the dead

They say Jesus defeated Death and came back. Why? Well, that opened a chance at resurrection for all the dead, essentially upgraded the link between the realms of the living and the dead. The game for that probably took all of five seconds to resolve as a clear win for Jesus. Drink a cup of this excellent wine or something.

In fantasy there are evil magicians and Gods enslaving the dead. People fighting to release the dead might get a really easy game too.

Maintain divine order

In some settings with active gods almost anyone can be resurrected if a powerful priest makes the effort. The implied game here is to get a proxy for a God to plea for you. This works because it makes direct or indirect service (give money to the temple) of Gods valuable and thus helps the Gods do their work. Whatever that is.

But anyone working for Gods can presumably benefit from this break in settings where it works at all.

Work among the living

If Death has some unspecified things he wants done among the living, a living agent would be more convenient than interfering with the living directly. Death rarely sees need for such but if there is someone silly enough to plan overthrowing Death, it might amuse him to "try to stop" that.

Amusement

If either your idea or you yourself is fun or entertaining, Death might want to meet you again. He does have a reputation for having a hidden sense of humor he gets to exercise way too rarely.

Persuade him that Life is the game

You need to choose a game that he will win and satisfy his desire to win, but that you will also win too.

That game is the game of Life. Pursuade him he will claim your life anyway, and ultimately he wins, but you get to live meanwhile. He doesn't even need to expend any effort, and does not need to interfere, as it is fairly inevitable you would die in your new Life. In fact, that could be the Game: You go through Life as normal, he bets you would die even without his influence, and you will. Couldn't be simpler really.

For Death it has the following benefits:

• He will win 100% of the time, again and again.


• Time in fact has no meaning to him, an instant for him could mean a lifetime for you.


• It could be quite entertaining for him, looking at you live life and all the 'close calls' you would make, which for any one of us would be dozens. He would get an adrenaline rush every time, same as we would when we watch close moments in sports.


• He will look very good to his superiors as he wins all the time, and eventually you will always 'lose' to come to him.


• It also ensures Death has a reoccurring job - without resurrecting you he would be finished and have nothing more to do with you

For You:

• You get to live a normal life, at least for a time


• You know you will die again eventually, but wouldn't we all?

"I Lost."

It has three simple rules.

-- Everybody is playing the game at all times. Knowing the rules is enough to turn you into a player.

-- If you lose the game, you should announce loudly to those around you "I lost".

-- You lose the game the moment you remember you're playing it.

If the player loses before proposing the game to death, nothing happens, since there is no bet yet.

Once you tell the game to Death, he is already playing it, since this game doesn't need consent to play. Since Death has a faster mind, and lives several minutes in a single human minute, he will always lose before his opponent.

Even if Death doesn't accept this game and ask you to come up with something else, he hates to lose - and you just implanted some sort of mental virus on his mind that he can't get rid off and will make him lose again, and again, and again, for the rest of his eternal existence.

Okay, so it seems like the only way to beat death is to trick him into thinking he will win a game, when in fact there's 35%+ chance he won't. How can we do this? The trick is to act irrationally.

This will require some prep work before you die.

1. Become a genius mathematician.


2. Solve some conjecture, such as the collatz conjecture, without death knowing. This probably implies doing so in secret. This is the irrational part. It makes no sense to not publish the results, since doing so will make you a great figure in history. Risking that is not worth an extra life, which you will lose anyways (unless winning the game makes you immortal).


3. Act super prideful during life. Tell people that you are the greatest mathematician in the universe.


4. Die

Now, when Death asks you what game you want to play, tell him that you want to play the "who can solve this conjecture first" game. Death will surely laugh, saying how he is the best mathematician in the universe, and will easily solve it within an hour. You reply that actually you are the greatest mathematician in the universe, and so will beat him. Death will laugh again, and gladly accept the challenge, for he will assume that your choose this game because of your vain pride.

Once he accepts, right down the solution and say "done". Death will obviously be dumb-founded, even angry, but will have to give you back your life. As a bonus, in your second life, you can reveal the solution, becoming famous.

Note that this will likely only work once, since Death will figure out that you actually solved it ahead of time, duping him. You'll have to use another answer the second time around.

Magic: the Gathering

At first glance, Magic seems like a terrible choice. After all, Death can control all probability, and random chance plays a huge factor in games of Magic. If Death can order their deck any way they want then they can win every match before the first turn. But there is a catch!

Magic rules are extremely comprehensive (pun intended), and they include a definition of shuffling:

701.19a To shuffle a library or a face-down pile of cards, randomize the cards within it so that no player knows their order.

Death cannot control the ordering of their deck, as that would be inconsistent with the definition of shuffling. Therefore it is possible to play Magic without Death having a massively unfair advantage.

Challenge him to a back-and-forth quiz regarding a subject that fulfils both of the following conditions:

1. You know everything about, such that Death cannot ask a question you cannot answer


2. There is a recent fact only known by yourself and people who are still alive
   

Since "There can be no new information from the world of the living in Death's domain", Death will not yet know the answer to the question you ask based on the second point.

Choose a cooperative players-vs-the-rules game, such as Star Trek: The Next Generation Interactive VCR Board Game - A Klingon Challenge.

Death is now playing on your side. When he wins, you win. Claim your life.

If he decides to throw the game, Death has lost. Claim your life.

ASSUMPTION:

Many-worlds interpretation,

Time travel

CHANCHE that a you wins against death in one timeline: 100%

IDEA:

Game:
Death wins if he manages to travel back in time and make the alternate timeline you win against the alternate timeline death by beating the alternate timeline death in a duel in the alternate timeline that he constructs by time travel.

The other you in the alternate timeline will meet the death from your timeline, and will propose the death from the alternate timeline the duel with the death from your timeline as game.

One of the deaths will loose the duel, loosing the game against one of the yous.

Exactly one you will win against the death in his timeline.

WOULD DEATH PLAY?:

The duel with the other timeline death is a fair game with an adequate opponent.

Why shouldn't he play?

Simply sacrifice yourself (or soul) for this opportunity to help humanity. Ask death to play a game of answering one question. In your stipulations you said death would be infinitely knowledgeable if he were ever alive, so I wonder if he can actually answer it? But ask that you are able to have one person available to hear the answer from death. The rules are if he answers the question correctly with proof he gets your soul, if he doesn’t you are allowed to live. And then simply ask some important question for humanity or life on earth or something. Like:

what shape is the universe? Or what is the meaning of life? What happens when we die? Is life a test? How do we save the earth from ourselves? Is there a god? Can we find a unified theory in physics? What is dark matter? Is this a mistake I am paying for and where did I go wrong? Is there other life in the universe?where am I going after this? Or make it simple. Whatever you want. Why was I here in the first place?

At best maybe death finds a reason to let you live. Maybe the game you want to play says more about why you should live than trying to win the game.

The game is that each player must choose a champion from among the dead to compete for him.

Whoever Death chooses, you choose the same person! If Death asks you to choose first, you say: "I choose the same person as you."

Blackjack.

Death gets to be the dealer which instantly gives him a slight advantage.

Not much knowledge has to be known by the other person, except when to hit and when to stay. This still gives that person a rough chance of "living" of 42%.

Death gets an even bigger advantage if the person playing doesnt know when to hit or stay.

I searched my closet for obscure solutions that Death might not know of.

1: A game called Breakthru [sic] has the property of appearing to be rather lopsided but I have personally developed a cook[1] in the opening that completely negates the lopsidedness. The game almost never draws although it's possible to do so. No person who has seen my personal cook has yet died so Death literally can't know it unless he can independently develop it.

2: A game called Mind Maze (which involves a hidden board) in which real physics applies and at which I have practice to the point of I'm almost playing with a visible board now. This does not involve cheating nor intelligence and nothing will replace the practice required. But a read over of the rules does not reveal any clue this is actually possible. Simply knowing its possible (as is immediately revealed on doing it) does not reveal the actual technique involved and it can't be done arbitrarily fast anyway. Even if Death could develop the same ability in a few tens of moves (much faster than my sister who actually managed it after awhile) the initial boost is enormous and very nearly outweighs any skill at mazebuilding or mazesolving.

[1]: deviation from book play William F Ryan, Scientific Checkers Made Easy

Both a roll a six sided dice. Whoever rolls higher wins. Reroll on ties.

Know, you might say that death could make you roll a 1 and himself roll a 6. But there is one rule of the game I forgot to mention. Death must allow the dice to fall randomly.

Since you are assuming Death is true to form, he won't break this rule.

An extremely chaotic system. Give each player a second or so to make a guess on the outcome of the system after a certain number of iterations. This gives Death only about a 50% chance of winning. The exact parameters can be determined randomly so that each player can use no outside knowledge. It should be sufficiently chaotic that in the time of the determination of parameters, Death can not choose which parameters are more predictable and allow him to win.

To ensure that Death does not reject the game, make sure that it is simple and looks to be easy to predict in a couple of minutes.