Restoring Java 8 compatibility isn't impossible at this point, but we are using "new" (added in 2017) methods, such as InputStream.readAllBytes() and InputStream.transferTo().
Technically, none of our Java 8 incompatibilities impact the server, except that we are building to --release=11, which will produce bytecode that Java 8 cannot read/run. We could in theory spend some time breaking up the build while still in Ant to compile gwt-servlet separate from gwt-user, but that's going to require some time to achieve. I also have ambitions for GWT 2.14 or so to be reworked into much smaller modules as part of mavenization (or gradle-ization, with an appropriate sponsor for the required build work), which would make that easier, but it isn't a goal of the work. A simpler version could just be to isolate a few classes/packages to run the gwt.javac targets on as either 8 or 11, but care will need to be taken so that this won't conflict/collide with the javax/jakarta split...
Another option could be reverting/rewriting some recent work (deprecating/removing the grab-bag Util/Utility classes), and will also require avoiding upcoming Java FlightRecorder changes (to replace SpeedTracer, which doesn't exist as a runnable Chrome plugin any more, as far as I can tell).
Finally, we could (as has been discussed in the past) consider backporting important changes to a Java 8 compatible branch. Naturally it wouldn't make sense to support any JDT updates, newer JRE emulation or large refactors for future modularization, but I'm sure some commits might make sense to backport (Java 8 String.split semantics perhaps?).
But as it stands, we are going to lose Java 8 support on the server in GWT 2.13 without some volunteered/sponsored efforts.