As things stand right now...
Of the Cubs minor leaguers who will be first-time eligible for the Rule 5 Draft post-2016, switch-hitting CVictor Caratini (link is external) (a Braves Top 10 Prospect acquired by the Cubs in a 2014 trade deadline deal for LHRP James Russell and IF-OF Emilio Bonifacio), RHSP Duane Underwood Jr (link is external) (Cubs 2012 2nd round draft pick), RHRP Armando Rivero (link is external)(ex-Serie Nacional closer who received a $3M+ bonus iwhen he signed with the Cubs in 2013) , LHSP Rob Zastryzny (link is external) (Cubs 2013 2nd round draft pick), RHSP Paul Blackburn (link is external) (Cubs 2012 Supplemental 1st round draft pick received when MLB Article XX-B FA 1B Carlos Pena signed with the Tampa Bay Rays post-2011), RHRP Ryan McNeil (link is external) (Cubs 2012 3rd round draft pick) , and OF Jake Hannemann (link is external) (Cubs 2013 3rd round draft pick) are probably the only ones who have a legitimate shot at being added to the Cubs MLB Reserve List (MLB 40-man roster) prior to the 11/20 deadline, but it's by no means sure that all of them or even most of them will be added to the 40.