Proponents say the policy maintains troop morale. Victims, many of whom spoke at Daley Plaza, call it discrimination. A ceremony held on Wednesday is America's first civic salute to lesbian, gay, bisexual and transgender veterans.
An Iraq War submarine veteran who had a stellar record with the military said the fear of blackmail led him out of the service.
"If there was no ban and I were allowed to openly serve, I wouldn't have had any of those extra stressors, I wouldn't have had any of those extra worries, and I would have re-enlisted," said Steven Lorandos, former US Navy officer.
Such regret resonates with Private Ed Zasadil 66 years after serving in World War II.
Many are hopeful that the Don't Ask, Don't Tell policy will be repealed.
"I just came back from Iraq and I wasn't able to see black, white, female, male gay or lesbian soldiers. They were all Americans fighting for us. And it is extraordinary that anyone would not want to let them serve and help our country," said Rep. Mike Quigley, (D) Chicago.
Quigley is a sponsor of House Resolution 1283, which asks President Obama to repeal Don't Ask, Don't Tell. Gay veterans have marched for years in the country's biggest Memorial Day parade, and the repeal is a campaign commitment of the commander in chief. As taps are played to honor all LGBT veterans, Private Zasadil recounts the lie he had to live -- just to serve his country.
"Well they asked me when I was drafted, 'Are you homosexual?' and I said 'No.' I didn't want to let anyone know, that was my private life and it was my business to tell if I wanted to... So I kept it quiet all those years," said Private Zasadil.
According to congressional records, since 1994 about 13,000 gay military members have been discharged at a cost of over $363 million. In a recent Gallup poll, 695 of Americans supported gays serving openly -- and in that poll 58% of self-identified conservatives agreed.
"Well I think that is why we should repeal Don't Ask, Don't Tell right now .I think the country is ready for this because they see it as fundamentally fair," said Quigley.
A recent Palm Center Study by a panel of military law experts argues that President Obama can suspend the gay discharge process through executive action.
On average, two military members are discharged per day because of Don't Ask Don't Tell.