Same problem here. Since I upgraded to Trusty Tahr syslog stopped rotating.
$ /var/log# ls -la syslog*
-rw-r----- 1 syslog adm 35897990 Sep 24 14:10 syslog
-rw-r----- 1 syslog adm  3083621 Aug 19 06:36 syslog.1
-rw-r----- 1 syslog adm    37647 Aug 18 06:43 syslog.2.gz
-rw-r----- 1 syslog adm    40009 Aug 17 06:42 syslog.3.gz
-rw-r----- 1 syslog adm    60140 Aug 16 06:39 syslog.4.gz
-rw-r----- 1 syslog adm    63035 Aug 15 06:38 syslog.5.gz
-rw-r----- 1 syslog adm    59387 Aug 14 06:40 syslog.6.gz
-rw-r----- 1 syslog adm    66224 Aug 13 06:30 syslog.7.gz

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https://bugs.launchpad.net/bugs/1278193

Title:
  logrotate skip the rotation of many files under /var/log due to bad
  group ownership

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