After a federal magistrate denied him bail yesterday, Joseph "Mousie" Massimino, the reputed underboss of the Philadelphia mob, left the courtroom shaking his head.

It wasn't a close call for U.S. Magistrate L. Felipe Restrepo.

John Han, a trial lawyer with the U.S. Department of Justice, said Massimino, 61, had a criminal case file dating to 1968 with 40 arrests, including three prior felony drug convictions, and a 2004 conviction in New Jersey for racketeering and related offenses for which he was sentenced to 10 years. (He was paroled in 2009 after serving five.)

According to Han, Massamino potentially faces a sentence of up to 21 years under advisory sentencing guidelines if convicted of all charges. The prosecutor said Massimino had demonstrated over the years an "absolute unwillingness" to abide by the law.

Defense attorney Robert Gamburg noted that the drug convictions dated back 30 years, that the new charges didn't involve actual or even threatened violence and that Massimino had always shown up for official proceedings while on parole for the 2004 racketeering conviction in New Jersey.

But Restrepo said he was "not comfortable," given the potential sentence, that there were any conditions short of keeping Massimino locked up to assure his future court appearances.

Massimino was charged Monday, along with reputed mob boss Joseph "Uncle Joe" Ligambi and 11 others, in the biggest indictment in more than a decade against the Philadelphia mob.

Authorities said Massimino, Ligambi and co-defendant Anthony "Ant" Staino Jr. set up a front company called JMA Industries that they used to facilitate the video-poker-machine business.

The machines were allegedly set up in bars, restaurants, convenience stores and coffee shops in Philadelphia and the burbs.

Massimino also allegedly extorted yearly "tribute payments" from a mob bookie from 2002 to 2006 so he could avoid personal harm and disruption of the illegal bookmaking operation. (Part of that time period he was behind bars in New Jersey.)

He pleaded not guilty to all the charges yesterday.

Bail hearings for two other defendants in the case - Martin "Marty" Angelina, 48, and Gary Battaglia, 50 - were continued until Tuesday.

Thus far, four defendants, including Ligambi, have been denied bail and five have been released on bail. Two others are in prison on unrelated charges and have not yet been arraigned.