A Jordan curve is an injective continuous map from $S^1$ to $\mathbb{R}^2$.
If $\gamma_1,\gamma_2,\gamma_3,\gamma_4$ are four counter clockwise Jordan curves, such that $\gamma_{i+1}$ is contained in the exterior region of $\gamma_i$ for each $i=1,2,3$. Let $A$ be the intersection of the of exterior region of $\gamma_1$ and the interior region of $\gamma_4$, is it true that there is a homotopy from $\gamma_2$ to $\gamma_3$ in $A$?
Here homotopy means homotopy as maps from $S^1$ to $\mathbb{R}^2$.
I thought this seems reasonable, but I couldn't come up with a proof myself, although I do think we may assume that $\gamma_i$'s are all polygonal curves, but it is still hard after that.
Maybe it is possible to use the Jordan Schoenflies theorem, generalized to four curves?
By "homotopy from $\gamma_2$ to $\gamma_3$ in $A$" do you mean a homotopy between maps $\gamma_2 : S^1 \to A$ and $\gamma_3 : S^1 \to A$ where each is a homeomorphism onto its image? If so, the answer is "no" but only for trivial reasons.
Using the convention $S^1 = \{z \in \mathbb{C} : \lvert z \rvert = 1\}$, we can define the maps $\gamma_i : S^1 \to \mathbb{R}^2$ by
$$\gamma_1(e^{it}) = (\cos(t), \sin(t))$$ $$\gamma_2(e^{it}) = (-2\cos(t),-2\sin(t))$$ $$\gamma_3(e^{it}) = (3\cos(t),3\sin(t))$$ $$\gamma_4(e^{it}) = (4\cos(t),4\sin(t))$$
The region $A$ in this case is an annulus, so it's clear that $\gamma_2$ and $\gamma_3$ are not homotopic: they represent different elements of $\pi_1(A) \cong \mathbb{Z}$!
Edit: you might also mean some kind of isotopy, e.g. a homotopy $H$ from $\operatorname{id}_A$ to some map $A \to A$ such that $H(t,{-}) : A \to A$ is a homeomorphism for all $t$ – I'm not sure what's possible in this interpretation.
Edit: Assuming $\gamma_2$ and $\gamma_3$ have the same orientation, the answer ought to be yes (I think, I have an unjustified step). First, homotope $\gamma_2$ and $\gamma_3$ inside $A$ to polygons $p_1$ and $p_2$ (respectively) so that they stay in the interior/exterior regions of each other the entire time (I'm not 100% sure this is possible?). Let $A'$ be the region between these polygons. It's clear that $A'$ deformation retracts onto either of its polygonal boundary curves, which induces isomorphisms $f_i : \pi_1(A) \to \pi_1(B_i) \cong \mathbb{Z}$, where $B_1$ is the "interior boundary" and $B_2$ is the "exterior boundary". Since $[p_1]$ generates $\pi_1(B_1)$ and $[p_2]$ generates $\pi_1(B_2)$, $f_1^{-1}([p_1]) = \pm f_1^{-1}([p_2])$ in $\pi_1(A') \cong \mathbb{Z}$. But $p_1$ and $p_2$ are both oriented counterclockwise, so we conclude that their homotopy classes are equal. Now we have a chain of homotopies $\gamma_2 \to p_1 \to p_2 \to \gamma_3$, all of which stay inside $A$.