A few years before 2008, the South Shore Little League folded, leaving many of the kids in the area without a sport to play competitively in the springtime. In response, ex-coach for the folded South Shore league and DePaul alumnus, LaVonte Stewart, created Lost Boyz, his own youth baseball league.
In its first year, Lost Boyz was just one youth baseball team, consisting of 15 kids, Stewart coached himself. In his program Stewart was both the head of the league as well as a coach, and because of this, he spent more time and became very close with the kids on his team.