Let $(\Omega,\mathcal{F},\mathbb{P})$ be a probability space and $(\mathcal{X},d)$ be a complete, separable, locally compact metric space. Suppose that $X,X_1,X_2,X_3,... : \Omega\to\mathcal{X}$ are $\mathbb{P}$-i.i.d. random variables.
Define: $$\forall m\in\mathbb{N}, \pi_m: \mathcal{X}\times\mathcal{X}^m\to\{1,...,m\}, (x,x_1,...,x_m)\mapsto \min\left(\operatorname{argmin}_{k\in\{1,...,m\}}\left(d\left(x,x_1\right),...,d\left(x,x_m\right)\right)\right).$$ Define: $$\forall m\in\mathbb{N}, Z_m:\Omega\to\mathcal{X}, \omega\mapsto X_{\pi_m\left((X(\omega),X_1(\omega),...,X_m(\omega)\right)}(\omega).$$
If $A$ is a open set of $(\mathcal{X},d)$, is it true that: $$\limsup_{m\to+\infty}\mathbb{P}_{Z_m}(A)\le\mathbb{P}_{X}(A)?$$
Edit 1: or maybe that there exists a constant $C>0$ independent of $A$ such that: $$\limsup_{m\to+\infty}\mathbb{P}_{Z_m}(A)\le C\cdot \mathbb{P}_{X}(A)?$$
If it is false in general, what if we add the hypothesis that $\mathcal{X}=\mathbb{R}^n$, $d$ is the Euclidean distance and $\mathbb{P}_X$ is absolutely continuous w.r.t. Lebesgue measure in $\mathbb{R}^n$?
Edit 2: in this last case, we have that if $B$ is a ball of $\mathbb{R}^n$, then $\mathbb{P}_X(\partial B)=0$ so, since $\mathbb{P}_{Z_m}\to \mathbb{P}_{X}$ in distribution (as explained below by WoolierThanThou), we have that $\mathbb{P}_{Z_m}(B)\to\mathbb{P}_{X}(B), m\to \infty$. Now, since by Besicovitch covering theorem there exist an universal constant $C_n\in\mathbb{N}$ such that every open subset $A$ is the union of at most $C_n$ open sets $A_1,...,A_{C_n}$ each of them is a disjoint countable union of open balls, say $A_i = \cup_{j\in I_i} B_{i,j}$, we have that: $$\mathbb{P}_{Z_m}(A)\le \sum_{i=1}^{C_n}\mathbb{P}_{Z_m}(A_i)= \sum_{i=1}^{C_n}\sum_{j\in I_i}\mathbb{P}_{Z_m}(B_{i,j}) = (*)$$ Now, if only we could exchange the limit and the series, we obtain that $$(*)\to \sum_{i=1}^{C_n}\sum_{j\in I_i}\mathbb{P}_{X}(B_{i,j})= \sum_{i=1}^{C_n}\mathbb{P}_{X}(A_i)\le \sum_{i=1}^{C_n}\mathbb{P}_{X}(A) = C_n \mathbb{P}_{X}(A) $$ Can anyone see a reason why could we exchange the limit an the series?
Well, $Z_m$ converges to $X$ in probability! For any, $\varepsilon>0,$ we have, by independence and identical distribution,
$\mathbb{P}(d(Z_m,X)\geq \varepsilon)=\mathbb{P}( \cap_{k=1}^m (d(X_k,X)\geq \varepsilon))=\mathbb{P}( d(X_1,X)\geq \varepsilon)^m$,
which goes to $0$, so long as we can show that $\mathbb{P}( d(X_1,X)\geq \varepsilon)\neq 1$. Clearly, the universe is broken if this isn't true, but you can note that if $(x_n)_{n\in \mathbb{N}}$ is a dense, countable subset of $\mathcal{X}$, then $\mathcal{X}=\cup_{n=1}^{\infty}B(x_n,\frac{\varepsilon}{2}),$ and hence, there must be some $n_0\in\mathbb{N}$ such that $\mathbb{P}(X\in B(x_{n_0},\frac{\varepsilon}{2}))\neq 0.$ Hence, by the fact that they're i.i.d., $\mathbb{P}(X,X_1\in B(x_{n_0},\frac{\varepsilon}{2}))\neq 0$, establishing the desired.
Of course, one might ask, does convergen in probability still imply weak convergence of the underlying measures? Well, assume $Y_n\to Y$ in probability with $Y_n$ and $Y$ $\mathcal{X}$-valued and fix $C\subseteq \mathcal{X}$ closed. Then, for any $\varepsilon>0$, denote $C_{\varepsilon}=\cup_{x\in C} B(x,\varepsilon)$
$$\mathbb{P}(Y_n\in C)\leq \mathbb{P}(d(Y_n,Y)\geq \varepsilon)+\mathbb{P}(Y\in C_{\varepsilon})$$
By continuity of measures (and the fact that $C$ is closed), we in particular find that
$$\limsup_{n\to\infty}\mathbb{P}(Y_n\in C)\leq \limsup_{n\to\infty} \mathbb{P}(Y\in C_{1/n})=\mathbb{P}(Y\in C),$$
which is equivalent to weak convergence of distributions in a complete, separable space.
Adding these things up, we get for $A\subseteq \mathcal{X}$ open, by weak convergence, that $\liminf_{m\to\infty} \mathbb{P}(Z_m\in A)\geq \mathbb{P}(X\in A)$, so your hypothesis is only true if $\lim_{m\to\infty}\mathbb{P}(Z_m\in A)=\mathbb{P}(X\in A)$.