I filed a bug report about this at https://trac.videolan.org/vlc/ticket/18956 before realizing there was an existing bug report for this exact same bug right here. Sorry about that. My bug report there does have a lot more details about this bug, for instance it started in version 2.2.5 of VLC for macOS, not 2.2.6. The last version of VLC for macOS not to have this bug is 2.2.4. And no it does not occur on Windows. Some files with SubStation Alpha / Advanced SubStation subtitles do work on recent versions of VLC for macOS and others do not.
I go into a LOT more detail in that bug report I filed. I did not find this bug report at first prior to filing my report because I was searching for a bug report with the word "subtitle" in it and did not get this as a result. Later after filing my report I found this when looking at macOS-specific bugs and it appears I mistakenly filed a bug report for something that already had one. Anyway my bug report has many useful details about this bug here. Perhaps it would be best to copy and paste my detailed bug report as a comment here on this one, and then close my bug report as a duplicate of this one, although I will refrain from copying and pasting it myself because I do not know your procedure for dealing with this type of situation and do not want to get in your way of solving the problem. So instead I am just posting comments on both the bug report I posted as well as this one regarding my mistake of creating another report on the same exact bug. Thanks and also sorry.
I have tested in more versions of VLC on macOS on a video affected by this issue. In the release versions, this bug occurs in 2.2.5, 2.2.5.1, and 2.2.6, with 2.2.6 being the current stable release. It does not affect release 2.2.4 or earlier. I am unable to test versions prior to 2.2.2 because they don’t work on Mac OS X 10.11 El Capitan or macOS 10.12 Sierra, but versions 2.2.2, 2.2.3, and 2.2.4 all work and do NOT have this bug.
In the nightly releases, this bug affects all of the 2.2.5, 2.2.6, and 2.2.7 nightlies currently available for download, from the oldest one, vlc-2.2.5-20160621-2150.dmg, to the newest one, the vlc-2.2.7.dmg nightly that has a file date of 14-Sep-2017. Those 2.2.5-2.2.7 nightlies are otherwise pretty stable but they ARE affected by this bug.
However this bug does NOT affect ANY of the 3.0.0 nightlies currently available for download, from the oldest one, vlc-3.0.0-20160719-0342-git.dmg, to the newest one, vlc-3.0.0-20171021-0500-git.dmg. The 3.0.0 nightlies are otherwise somewhat unstable but they do not have THIS bug.
commit 974665ab641ded6f8df07f87d23e07f948459724Author: Felix Paul Kühne <felix@serioese.gmbh>Date: Sun Oct 22 17:51:55 2017 +0200 contrib/libass: fix CoreText detection on OS X < 10.8 (fixes [#18583](https://code.videolan.org/videolan/vlc/-/issues/18583))
and
commit 9b9b6218e54bad35a8065ca39e8076a755b0969cAuthor: Felix Paul Kühne <fkuehne@videolan.org>Date: Sun Dec 4 13:34:12 2016 +0100 contrib/libass: don't enforce use of fontconfig on appleOS (cherry picked from commit 8a922414eb3bc08e5458371f7618dc7f5378caaf)