The Chicago Cowboys, formerly the Midway Cowboys, of Chicago's Ironman Football League(full-contact no-pad), came into existence 25 years ago. A bunch of teenage young men would gather every weekend to play pick up football games in the back yard of the Vista Garden housing complex, located on Chicago's famous Southside. These young men, love for the game, grew and grew, until they decided to venture out of the neighborhood. They would walk miles to different parks, in search of teams to play. As the years passed, the numbers of players dwindled. Out of many, four young men pressed on and straddled with their love, dedication and desire to play football, they formed the Midway Cowboys. There were many guys, from various neighborhoods throughout Chicago that shared the same passion as those four young men. Not only did they all have football in common, but they all needed a release from the troubles from everyday life in our impoverished communities which ravaged with gangs, drugs and violence. Those young men considered themselves the lucky ones, because they had each other to lean on in troubled times. Out of this desire and friendship, an unbreakable family bond was created. Once you were accepted as a "Cowboy", you were forever to be accepted as a brother or sister. Your family became our family.

With the atmosphere of family resonating amongst the Cowboy family, they were able to become successful on the football field. So successful that the Midway Cowboys and the Hillcrest Hitmen, formed Chicago's Ironman Football League. The league consisted of teams from all over the city and suburbs and played a brand of football that only the original gridiron greats would appreciate. Some ridiculed, laughed and called them crazy; unfortunately, they could not see that this league provided many young people with an outlet from everyday trials and tribulations. Every Sunday, there were 20 to 40 guys per team along with some family members gathering in parks across the city and suburbs, to watch a football game regardless of weather conditions. Sun, rain, snow, heat, wind, or sub zero temperatures, it did not matter. These players sacrificed and displayed true commitment, dedication, and a change from the norm. Yes, football changed and saved lives.

Still, today the Chicago Cowboys believe that they can turn around wayward young men. They can give them a chance at life through a positive atmosphere. All that they ask is that you stay LOYAL, DEDICATED, RESPONSIBLE and that you carry a POSITIVE ATTITUDE. Not just on the gridiron but through your walk in life. We are MEN and we continue in our quest to build character in those who lack it and courage in those who want it. Cowboys football is not just a brand but a Legacy.