The GUI is optional these days, and there's plenty of Windows servers that don't use it. The recommended administration approach these days is PowerShell remoting, often over SSH now that Windows has a native SSH server bundled (based on OpenSSH).
I'd say having a GUI is not inherently stupid. The stupid part is, if I understand it correctly, the GUI being a required component and the primary access method.
Yeah. Thankfully, Windows server cleaned up that stupidity starting around 2006 and finished in around 2018.
Which all sounds fine until we meditate on the history that basically all other server operating systems have had efficient remote administration solutions since before 1995 (reasonable solutions existed before SSH, even).
Windows was over 20 years late to adopt non-grapgical low latency (aka sane) options for remote administration.
I think it's a big part of the reason Windows doesn't appear much on this chart.