We know that, in general, the operator norm of a matrix is larger than its spectral radius: $\|A\|_{\rm op}\ge r(A)\equiv \max_{\lambda\in\sigma(A)}\lvert \lambda\rvert$, where $\sigma(A)$ denotes the spectrum of $A$.
If $A$ is normal, these quantities are clearly the same, as $\|A\|_{\rm op}$ equals the largest singular value of $A$, which equals the largest $|\lambda|$ for $\lambda$ an eigenvalue of $A$.
I can also find examples of $\|A\|_{\rm op}=r(A)$ for $A$ not normal, by building it as direct sum of a non-normal matrix and a matrix with a large eigenvalue. E.g. $$\begin{pmatrix}2 & 0 & 0 \\ 0 & 1 & 0 \\ 0 & 1 & 1\end{pmatrix}.$$ This is not diagonalisable, but satisfies the equality.
Are there such examples with simple matrices? In other words, given a simple $A$ (i.e. a matrix composed of a single Jordan block), can we have $\|A\|_{\rm op}=r(A)$?
Yes, but only when $A$ is $1\times1$. Note that every complex square matrix is unitarily triangulable. Suppose $B=U^\ast AU$ is such a triangularisation. Since all eigenvalues of $B$ are the same, we have $\rho(B)=|b_{jj}|\le\|\mathbf b_j\|_2\le\|B\|_2=\rho(B)$ for every $j$, where $\mathbf b_j$ denotes the $j$-column of $B$. It follows that $|b_{jj}|=\|\mathbf b_j\|_2$ for every $j$, i.e. $B$ is a diagonal matrix. As $B$ is similar to $A$ and the Jordan form of $A$ has only one Jordan block, $B$ and $A$ must be $1\times1$.
More generally, $\|A\|=\rho(A)$ for some submultiplicative matrix norm $\|\cdot\|$ if and only if every eigenvalue of $A$ with maximum modulus is semi-simple. For a proof, please see here.