If $X\subset\mathbb{R}^2$ is a connected open subset which is not simply connected, then there exists some point $p\in\mathbb{R}^2\setminus X$ such that the inclusion map $X\to\mathbb{R}^2\setminus \{p\}$ induces a nontrivial map on $\pi_1$. In other words, if a connected open subset of the plane is not simply connected, this is always because it contains a loop which winds around some point in its complement. More strongly, in fact, there is some point $p\in\mathbb{R}^2\setminus X$ such that $X$ contains a simple closed curve that has $p$ in its interior. (See here for one way to prove this.)
My question is whether this is still true for arbitrary (not necessarily open) subsets of $\mathbb{R}^2$. More precisely:
Suppose $X\subset\mathbb{R}^2$ is path-connected but not simply connected. Must there exist some point $p\in\mathbb{R}^2\setminus X$ such that the inclusion map $X\to\mathbb{R}^2\setminus \{p\}$ induces a nontrivial map on $\pi_1$? More strongly, must there exist such $p$ such that $X$ contains a simple closed curve that has $p$ in its interior, or at least a curve with winding number $1$ around $p$ (so the map on $\pi_1$ is surjective)?
I suspect the answer is yes, since I've heard of various results saying that arbitrary subsets of $\mathbb{R}^2$ are homotopically "tame" in various ways (for instance, unlike in higher dimensions, they cannot have nontrivial $H_k$ for $k\geq 2$). The closest result to my question that I know of is the result from this answer that if $X\subseteq \mathbb{R}^2$ then any nontrivial element in $\pi_1(X)$ remains nontrivial in $\pi_1(\mathbb{R}^2\setminus F)$ for some finite set $F\subseteq \mathbb{R}^2\setminus X$. This is very close to my question: it is weaker since it involves a finite set $F$ rather than a single point, but stronger since it applies to an arbitrary nontrivial element of $\pi_1(X)$ rather than just saying there exists an element of $\pi_1(X)$ that remains nontrivial. I would guess you can prove an affirmative answer to my question either from that result or using ideas similar to its proof, but I don't see an obvious way to do so. (Note that the finite set $F$ in that result cannot be reduced to a single point, since your element of $\pi_1(X)$ could be a commutator of loops around different points.)
(Alternatively, by the argument I linked above in the case of open subsets, it would suffice to show that there exists a nontrivial loop in $X$ with only finitely many self-intersections, since then you can use that to reduce to a nontrivial simple loop and then invoke the Jordan curve theorem.)