Let $\mathbb{C}^{*} = \mathbb{C} \setminus \{0\}$, and $U \subset \mathbb{C}^{*}$ an open, connected, not simply connected subset. Can we find a holomorphic $f : U \to \mathbb{C}^{*}$ such that $f_{\sharp} : \pi_1(U) \to \pi_1(\mathbb{C}^{*})$ (where I've omitted the choice of basepoint) is nontrivial?
So essentially we want to find a hole of $U$ and translate that hole to the origin (at least, this is the approach that comes to me). If we could find a Jordan curve lying inside $U$ which is homotopically nontrivial, I believe we could do the following: this Jordan curve bounds a (topological) disk. Clearly $U$ cannot contain all points in this disk or else the curve would be homotopically trivial. So take a point in the disk but not in $U$ and consider the translation which sends it to the origin; I believe that should induce something nontrivial on $\pi_1$.
However, I'm not sure if we can always find this Jordan curve. For instance, it doesn't seem to be true that every element of $\pi_1(U)$ can be represented by a Jordan curve (imagine the figure $8$ as an element of $\pi_1(\mathbb{C} \setminus \{0, 1\})$).