The 2003 PrideFest sustained a debt of nearly $150,000, and during mid-2003 the future of PrideFest was in grave doubt.

In the fall of 2003, a diverse group of community members pulled together an advisory group to chart the festival's options. Led by the Cream City Foundation (CCF), the PrideFest Task Force was formed to forge ahead with a plan to reduce the debt and produce a festival for 2004. The community had come too far to let the festival end so tragically. Drastic steps were taken, including shutting down the 12-month-a-year permanent office that PrideFest had rented out.

An appeal for help was made, and through amazing generosity, a group of people affectionately called the PrideFest Legacy Angels donated nearly $60,000 to pay down some of the debt. Their devotion to the mission of PrideFest helped create a belief that the festival could rise again.

The PrideFest Production Team and the Task Force donated thousands of hours to move forward with planning. For PrideFest 2004, the festival was reduced to two days and its budget was pared down to its most vital elements. Even the Pride Parade was eliminated, to many outcries among the community.

Despite the negative publicity and concerns, nearly 15,807 people attended and enjoyed an entertainment lineup that included national music sensations Kristine W. and Amber. Under near perfect skies all weekend, the festival had a rebirth of dramatic proportions. The community had truly stepped forward to support the festival.