[proofplan]
We start from the classical partial fraction expansion for $\pi\cot(\pi w)$, interpreted by symmetric summation, and differentiate it $k-1$ times. Since $k \geq 4$, the differentiated lattice sum is absolutely and locally uniformly convergent away from the integers, so the differentiated symmetric expansion becomes an ordinary series. On the upper half-plane, we rewrite $\pi\cot(\pi z)$ as a normally convergent geometric [Fourier series](/page/Fourier%20Series) in $q = e^{2\pi i z}$ and differentiate termwise. Comparing the two differentiated formulae gives the stated coefficient.
[/proofplan]
[step:Differentiate the cotangent partial fraction expansion into an ordinary lattice sum]
Define the [meromorphic function](/page/Meromorphic%20Function)
\begin{align*}
F: \mathbb{C} \setminus \mathbb{Z} &\to \mathbb{C} \\
w &\mapsto \pi\cot(\pi w).
\end{align*}
We use the classical cotangent partial fraction expansion, interpreted by symmetric summation,
\begin{align*}
F(w)=\lim_{N\to\infty}\sum_{n=-N}^{N}\frac{1}{w+n}
\end{align*}
for every $w \in \mathbb{C}\setminus\mathbb{Z}$ (citing a result not yet in the wiki: Mittag-Leffler partial fraction expansion for $\pi\cot(\pi w)$).
Fix a compact set $K \subset \mathbb{C}\setminus\mathbb{Z}$. Since $K$ has positive distance from $\mathbb{Z}$ and is bounded, the series
\begin{align*}
\sum_{n\in\mathbb{Z}}\frac{1}{(w+n)^k}
\end{align*}
converges uniformly for $w \in K$ whenever $k \geq 2$, by comparison with $\sum_{|n|\geq N}|n|^{-k}$. Therefore differentiating the symmetric partial fraction expansion $k-1$ times is valid on compact subsets of $\mathbb{C}\setminus\mathbb{Z}$. For each $n \in \mathbb{Z}$, the function
\begin{align*}
g_n: \mathbb{C}\setminus\{-n\} &\to \mathbb{C} \\
w &\mapsto \frac{1}{w+n}
\end{align*}
satisfies
\begin{align*}
g_n^{(k-1)}(w)=(-1)^{k-1}(k-1)!\frac{1}{(w+n)^k}.
\end{align*}
Hence, for every $w \in \mathbb{C}\setminus\mathbb{Z}$,
\begin{align*}
F^{(k-1)}(w)
=
(-1)^{k-1}(k-1)!
\sum_{n\in\mathbb{Z}}\frac{1}{(w+n)^k}.
\end{align*}
Equivalently,
\begin{align*}
\sum_{n\in\mathbb{Z}}\frac{1}{(w+n)^k}
=
\frac{(-1)^{k-1}}{(k-1)!}F^{(k-1)}(w).
\end{align*}
[guided]
The partial fraction expansion for $\pi\cot(\pi w)$ is not an absolutely convergent sum at order $1$, so it must be read as the symmetric limit
\begin{align*}
\pi\cot(\pi w)=\lim_{N\to\infty}\sum_{n=-N}^{N}\frac{1}{w+n},
\end{align*}
valid for $w \in \mathbb{C}\setminus\mathbb{Z}$ (citing a result not yet in the wiki: Mittag-Leffler partial fraction expansion for $\pi\cot(\pi w)$).
After differentiating, the situation improves. Fix a compact set $K \subset \mathbb{C}\setminus\mathbb{Z}$. Because $K$ is bounded and avoids the integers, there are constants $N_0 \in \mathbb{N}$ and $C_K > 0$ such that
\begin{align*}
|w+n| \geq \frac{|n|}{2}
\end{align*}
for all $w \in K$ and all integers $n$ with $|n|\geq N_0$. Thus
\begin{align*}
\left|\frac{1}{(w+n)^k}\right|
\leq
\frac{2^k}{|n|^k}
\end{align*}
for $w \in K$ and $|n|\geq N_0$. Since $k \geq 4$, in particular $k>1$, the numerical series $\sum_{|n|\geq N_0}|n|^{-k}$ converges. The Weierstrass test gives [uniform convergence](/page/Uniform%20Convergence) of
\begin{align*}
\sum_{n\in\mathbb{Z}}\frac{1}{(w+n)^k}
\end{align*}
on $K$.
Now define, for each $n \in \mathbb{Z}$,
\begin{align*}
g_n: \mathbb{C}\setminus\{-n\} &\to \mathbb{C} \\
w &\mapsto \frac{1}{w+n}.
\end{align*}
A direct repeated differentiation gives
\begin{align*}
g_n^{(k-1)}(w)=(-1)^{k-1}(k-1)!\frac{1}{(w+n)^k}.
\end{align*}
The locally uniform convergence just verified is exactly what is needed to differentiate the symmetric partial fraction expansion $k-1$ times away from its poles. Therefore
\begin{align*}
F^{(k-1)}(w)
=
\sum_{n\in\mathbb{Z}}g_n^{(k-1)}(w)
=
(-1)^{k-1}(k-1)!
\sum_{n\in\mathbb{Z}}\frac{1}{(w+n)^k}.
\end{align*}
Solving this identity for the lattice sum gives
\begin{align*}
\sum_{n\in\mathbb{Z}}\frac{1}{(w+n)^k}
=
\frac{(-1)^{k-1}}{(k-1)!}F^{(k-1)}(w).
\end{align*}
[/guided]
[/step]
[step:Expand the cotangent as a normally convergent Fourier series on $\mathbb{H}$]
Let
\begin{align*}
Q: \mathbb{H} &\to \mathbb{C} \\
z &\mapsto e^{2\pi i z}.
\end{align*}
For $z \in \mathbb{H}$, one has $|Q(z)|=e^{-2\pi\operatorname{Im}(z)}<1$. Using the identity
\begin{align*}
\cot(\pi z)
=
i\,\frac{e^{2\pi i z}+1}{e^{2\pi i z}-1},
\end{align*}
we obtain
\begin{align*}
F(z)
=
\pi i\,\frac{Q(z)+1}{Q(z)-1}
=
-\pi i\,\frac{1+Q(z)}{1-Q(z)}.
\end{align*}
Since $|Q(z)|<1$,
\begin{align*}
\frac{1+Q(z)}{1-Q(z)}
=
1+2\sum_{r=1}^{\infty}Q(z)^r.
\end{align*}
Thus
\begin{align*}
F(z)
=
-\pi i-2\pi i\sum_{r=1}^{\infty}e^{2\pi i r z}.
\end{align*}
Moreover, if $K \subset \mathbb{H}$ is compact, then there is a number $\rho_K \in (0,1)$ such that $|Q(z)|\leq \rho_K$ for every $z \in K$. For every integer $m \geq 0$,
\begin{align*}
\left|(2\pi i r)^m e^{2\pi i r z}\right|
\leq
(2\pi r)^m \rho_K^r
\end{align*}
for every $z \in K$ and every $r \geq 1$, and the numerical series $\sum_{r=1}^{\infty}(2\pi r)^m\rho_K^r$ converges. Hence the Fourier series for $F$ and all of its termwise derivatives converge uniformly on $K$.
[guided]
The upper half-plane is the region where the exponential variable has modulus strictly less than $1$. Define
\begin{align*}
Q: \mathbb{H} &\to \mathbb{C} \\
z &\mapsto e^{2\pi i z}.
\end{align*}
If $z = x+iy$ with $x,y \in \mathbb{R}$ and $y>0$, then
\begin{align*}
|Q(z)|=|e^{2\pi i x}e^{-2\pi y}|=e^{-2\pi y}<1.
\end{align*}
This is why the geometric expansion below is valid precisely on $\mathbb{H}$.
Using the exponential formula for cotangent,
\begin{align*}
\cot(\pi z)
=
i\,\frac{e^{2\pi i z}+1}{e^{2\pi i z}-1},
\end{align*}
we rewrite $F(z)=\pi\cot(\pi z)$ as
\begin{align*}
F(z)
=
\pi i\,\frac{Q(z)+1}{Q(z)-1}
=
-\pi i\,\frac{1+Q(z)}{1-Q(z)}.
\end{align*}
Since $|Q(z)|<1$, the geometric series gives
\begin{align*}
\frac{1}{1-Q(z)}
=
\sum_{r=0}^{\infty}Q(z)^r.
\end{align*}
Multiplying by $1+Q(z)$ yields
\begin{align*}
\frac{1+Q(z)}{1-Q(z)}
=
1+2\sum_{r=1}^{\infty}Q(z)^r.
\end{align*}
Therefore
\begin{align*}
F(z)
=
-\pi i-2\pi i\sum_{r=1}^{\infty}e^{2\pi i r z}.
\end{align*}
We also need termwise differentiation. Let $K \subset \mathbb{H}$ be compact. Since the continuous function $z \mapsto |Q(z)|$ is strictly less than $1$ on $K$, there exists $\rho_K \in (0,1)$ such that $|Q(z)|\leq \rho_K$ for all $z \in K$. For an integer $m \geq 0$, the $m$-th derivative of $e^{2\pi i r z}$ is $(2\pi i r)^m e^{2\pi i r z}$, and therefore
\begin{align*}
\left|(2\pi i r)^m e^{2\pi i r z}\right|
\leq
(2\pi r)^m \rho_K^r.
\end{align*}
The series $\sum_{r=1}^{\infty}(2\pi r)^m\rho_K^r$ converges because exponential decay dominates every polynomial power of $r$. The Weierstrass test gives uniform convergence on $K$ for the Fourier series and for each differentiated series. Hence differentiating termwise on compact subsets of $\mathbb{H}$ is justified.
[/guided]
[/step]
[step:Differentiate the Fourier series and compare the two formulae]
Taking $m=k-1$ in the termwise differentiation justified above, the constant term $-\pi i$ differentiates to $0$, and
\begin{align*}
F^{(k-1)}(z)
=
-2\pi i
\sum_{r=1}^{\infty}(2\pi i r)^{k-1}e^{2\pi i r z}
=
-(2\pi i)^k
\sum_{r=1}^{\infty}r^{k-1}e^{2\pi i r z}.
\end{align*}
Substituting this into the differentiated partial fraction identity at $w=z$ gives
\begin{align*}
\sum_{n\in\mathbb{Z}}\frac{1}{(z+n)^k}
&=
\frac{(-1)^{k-1}}{(k-1)!}F^{(k-1)}(z) \\
&=
\frac{(-1)^{k-1}}{(k-1)!}
\left(
-(2\pi i)^k
\sum_{r=1}^{\infty}r^{k-1}e^{2\pi i r z}
\right) \\
&=
\frac{(-1)^k(2\pi i)^k}{(k-1)!}
\sum_{r=1}^{\infty}r^{k-1}e^{2\pi i r z} \\
&=
\frac{(-2\pi i)^k}{(k-1)!}
\sum_{r=1}^{\infty}r^{k-1}e^{2\pi i r z}.
\end{align*}
This is the desired identity. The absolute convergence of the left-hand series follows from comparison with $\sum_{|n|\geq 1}|n|^{-k}$, and the absolute convergence of the right-hand series follows from $|e^{2\pi i r z}|=e^{-2\pi r\operatorname{Im}(z)}$ together with exponential decay.
[/step]