2002
- KSSM was founded when Jane Braswell (a krewe member from an all female krewe) and Jayne Lauve got together and enlisted the help of Randy Hann to put together an all inclusive Krewe. From humble beginnings holding meetings in krewe members houses, the Krewe of the South Shore Marauders was formed as a legal business with Randy Hann becoming KSSMs first president (2002 - 2006). From the very beginning, our youngest krewe members were in their early 20s and our oldest krewe members in their late 70s making KSSM one of the most age diverse krewes in existence.

2003
- Knowing that many students with an A grade point average would easily get scholarships, KSSM Foundation started presenting B and B+ senior high school students in the South Shore area with  scholarships. Since the beginning, the KSSM Foundation has awarded over $85,000 in scholarships to deserving students.

2004
- After renting multiple floats through the first few years, the first board members decided to have a float built that would become the our first pirate ship.

2005
- The first wedding during a Gasparilla parade was officiated on the KSSM float on January 29th between Aaron Malo and Terry Padgett, two of KSSMs founding krewe members.
- Pat Cosgrove elected President (2005 - 2007)

2007
- Rich Love elected President (2007 - 2009)

2009
- Randy Hann elected President (2009 - 2011)

2011
- Dena Laurain elected President (2011 - 2012)

2012
- Ellen Cyr assumed the President position after Dena left KSSM (2012 - 2013)

2013
- Aaron Malo elected President (2013 - 2017)
- After paying rental fees for 10 years, many members of the krewe loaned the krewe money to build a float. KSSM bought the old Brass Monkey float and had it towed to Joe Bailey's house where multiple krewe members lent a hand to tear apart the float and build up the new KSSM pirate ship we have today. The build team, led by Steve Preston (project manager), Barron Lynn and Joe Bailey (master carpenter/builders), spent 9 months building the new float to get it ready to make its first debut in the 2014 - 2015 parade season. 

2017
- Steve Preston elected President (2017 - 2019)

2018
- Float loans paid back to all members who loaned money to the krewe.

2019
- Cindy Feuer elected President (2019 - 2023)

2020
- The year of no parades. Covid struck the land but KSSM held together and lost virtually none of the members.

2021
- Axels needed to be replaced on the float and many members once again stepped up to loan the krewe money to make the needed repairs.
- KSSM becomes the first Gasparilla krewe to charter two BSA scout troops: Troops 284 and 384 in Riverview Florida.

2023
- Aaron Malo elected President (2023 - present)