The Leo Brothers Annual Memorial Softball Tournament began in 2005 as a brainchild of Leo's nephew Paul Brothers and Paul's close friend Paul Healey. The 1st tournament took place in August '05 at Alex Faulkner Sports Park in Bishop's Falls, Newfoundland. The tournament has grown each year and continues to gain momentum as more and more people have become involved. Since it's inception in '05, Leo's brother Tony Brothers and wife Susan have become instrumental in the success of the tournament.

Leo's Legends is a team that participates in the annual tournament and is comprised of many of Leo's family and friends. The 2007 edition of "Leo's Legends" was made up of brothers, nephews, cousins and friends. 2007 also saw "The Legends" first win in tournament history, as they went 2 for 3 in the round robin.