The question is about a modification of the following riddle (you can think about it before reading the answer if you like riddles, but that's not the point of my question):

**The Riddle:**
We assume there is an infinite sequence of boxes, numbered $0,1,2,\dots$. Each box contains a real number. No hypothesis is made on how the real numbers are chosen.
You are a team of 100 mathematicians, and the challenge is the following: each mathematician can open as many boxes as he wants, even infinitely many, but then he has to guess the content of a box he has not opened. Then all boxes are closed, and the next mathematician can play. There is no communication between mathematicians after the game has started, but they can agree on a strategy beforehand.

You have to devise a strategy such that at most one mathematician fails. Axiom of choice is allowed.

**The Answer:**
If $\vec u=(u_n)_{n\in\mathbb N}$ and $\vec v=(v_n)_{n\in\mathbb N}$ are sequences of real numbers, we say that $\vec u\approx \vec v$ if there is $M$ such that for all $n\geq M$, $u_n=v_n$. Then $\approx$ is an equivalence relation, and we can use the axiom of choice to choose one representative per equivalence class. The strategy is the following: mathematicians are numbered from $0$ to $99$, and the sequence of boxes $(u_n)_{n\in\mathbb N}$ is split into $100$ sequences of the form $\vec u_i=(u_{100n+i})_{n\in\mathbb N}$ with $0\leq i\leq 99$. Mathematician number $i$ will look at all sequences $\vec u_j$ with $j\neq i$, and for each sequence, it will compute the index $M_j$ from which the sequence matches the representative of its $\approx$-class. He then takes $M$ to be the maximum of the $M_j+1$ and looks at the sequence $\vec u_i$ starting at this $M$. He can deduce the $\approx$-class of the sequence $\vec u_i$, and guesses that $u_{M-1}$ matches the representive. At most one mathematician will be wrong: the one who has the number $i$ with $M_i$ maximal.

**The Modification:**
I would find the riddle even more puzzling if instead of 100 mathematicians, there was just one, who has to open the boxes he wants and then guess the content of a closed box.
He can choose randomly a number $i$ between $0$ and $99$, and play the role of mathematician number $i$. In fact, he can first choose any bound $N$ instead of $100$, and then play the game, with only probability $1/N$ to be wrong.
In this context, does it make sense to say "guess the content of a box with arbitrarily high probability"? I think it is ok, because the only probability measure we need is uniform probability on $\{0,1,\dots,N-1\}$, but other people argue it's not ok, because we would need to define a measure on sequences, and moreover axiom of choice messes everything up.

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