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What happened was that any builds that were supposed to have been triggered from GitHub PRs through the ghprb-plugin would fail to start. GitHub would show that the webhook was sent but the response came back as 500 (Internal Server Error)
Looks like when GitHub sends the payload via the ghprb-plugin webhook. ghprb-plugin starts to parse the payload and hits a "Null Pointer Exception" and fails to trigger a build to start. So the Jenkins builds are never executed.
Rolling back the Git Plugin to 2.3.4 makes things work again. I am running latest version(s) of Jenkins, Git Client, ghprb-plugin.