Charles Mark Cameron and mate Craig Jason Elston faced court on Friday charged with publicly displaying a Nazi symbol without reasonable excuse outside the Darlo Bar in inner Sydney the previous afternoon.
The pair, aged 44 and 51, were arrested at a second bar about an hour later amid heightened anxiety over anti-Semitism and a raft of attacks at Jewish sites in Sydney and Melbourne.
Cameron, who served 20 years in the Australian Defence Force before being medically discharged with PTSD and other issues, acknowledged it was a regrettable situation.
"(He) wishes to place on the record that he is not a person who holds any anti-Semitic views," Legal Aid lawyer Elliot Rowe told the court.
"In the current climate this is an extremely serious offence."
Elston, also a military veteran, was a collector of war memorabilia and had been "excited" to show off his latest acquisition, a German Nazi swastika flag, Downing Centre Local Court was old.
Showing it off involved pulling it from a bag and unfurling it at a table outside the bar, which is 90m from the Sydney Jewish Museum.
"He ... became excited that he had received it and that it would form part of his private collection," Mr Rowe said.
"It was a big mistake."
Elston also did not hold anti-Semitic views, Mr Rowe said.
The incident happened hours after federal parliament passed minimum one-year jail terms for publicly displaying prohibited Nazi or terrorist organisation symbols, or performing the Nazi salute.
But that law - passed with bi-partisan support - is still awaiting assent, meaning Elston and Cameron were charged under NSW law, carrying a maximum one-year jail term.
While acknowledging bail was not punitive in nature, Magistrate Greg Grogin said he could not be satisfied the community would be safe with Cameron on the streets.
"As a former member of the ADF, one would think he would be acutely aware of the actions like these can promote," the magistrate said.
"He must be also acutely aware, unless he has walked around with his head in the ground, of the current waves of anti-Semitism that are disgraceful, disgusting and abhorrent.
"If he's willing to do it once, there is an unacceptable risk he may be willing to do it again."
After the decision, Elston withdrew his own bail application and pleaded guilty.
Both men were remanded in custody until February 21, when Elston will be sentenced.
NSW also announced tougher penalties and new crimes on Thursday after escalating anti-Semitic graffiti, firebombings and most recently a thwarted plot targeting key Jewish sites.
Those changes will be before state parliament in the coming week.
Jewish groups have repeatedly aired concerns offenders are getting away with little more than a conviction and a small fine for crimes striking fear into the community.
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