The roots of the New York Long Island Strat League date back to Archbishop Molloy High School in the early 1990s, when Jack Flynn, Chris Forster and Jason Varvaro started a league with other Stanners. Every day after classes were over, the dice were rolled and league games were played in Molloy's cafeteria. The Molloy leagues were very different then the NYLISL - no year to year player protection, no at-bats or innings pitched minimums and a highly volatile ownership group that changed constantly - sometimes month by month.

 

In 1994, Flynn, Forster and Varvaro graduated high school and went their separate ways. Flynn went to St. John's and met future league members Jason Boland and Tim Walsh in the office of the Torch - the official student newspaper of St. John's University. In 1996, a six-team "Redmen" league was formed that included Flynn, Boland and Walsh and would later include Jim Baumbach, who started taking classes at SJU the same year. Meanwhile, the three Molloy boys eventually reconnected and even put together a four-team side league, using combination stock teams and an 80-game schedule.

 

By 1998, the two leagues were connected through a mutual enjoyment of Strat-o-Matic. League mebership was still volatile from year to year until 2000, when a mid-season decision to go to a keeper league format was approved. When fellow Stanner Joe Falzarano dropped out of the league for the first time that year, he was replaced by Baumbach's brother Kevin, who was a franchise owner until 2007.

 

League membership has maintained fairly constant over the NYLISL's 14 seasons - Flynn, Forster, Varvaro and Baumbach have fielded a team every year. Walsh's Old School Brothers suspended operations for the 2004 season and folded after the 2005 season. He returned in 2007 as The Riffs. Falzarano returned to the league for a brief period before being permanently banned from the NYLISL in 2005. In 2006, the league expanded for the first time and brought in veteran Strat player Ed Price. The second wave of expansion came a year later, when Walsh and Sean O'Leary were each granted new franchises.