The history of OSIAW.
We think it was October 1997 when Jon said to his friends “Oh Shit It’s Almost Winter” we need to play some golf! So we clipped our pagers on our belts, pocketed our OG Motorola Razors and hit the links. Just four of us and we decided to make it an annual event. OSIAW was born.
The first couple of years we raised a very small amount of money for Cystic Fibrosis. In 2003 Jon’s Mom died from ALS (Lou Gehrig’s Disease) and we got serious about raising money for the ALS Association of DC/MD/VA and over the next years we raised over $100,000.
Somewhere along the way we had a rain out and the rain date was the day before Halloween so we invited everyone to wear their Halloween costumes. They did! And then things really took off with themed costume golf events every October. It was wild and everyone had a blast. Plus everyone had a Blackberry and we were so cool.
Along the way we had many themes including Rock n Roll, America, Pirates, Island Theme and others.
We had forgotten to have the event in one of the early years so we had our 20th and final event in 2018. Go out on top was the idea and we sure did with a blowout Caddyshack themed event. Wow what a day!
In December 2025 Jon’s long time buddy Eddie Augustine asked Jon if he would do just one more OSIAW to support his United Blood Cancer fundraising campaign. Jon said “no” . And after about 30 seconds of remembering how important Eddie and his family’s story are Jon changed his mind and said “yes”. See link to that story here
So here we are. One last curtain call for OSIAW. Please sign up and/or donate on the home page.