After nearly 20 years on the lam, James 'Whitey' Bulger, former head of Boston's Winter Hill Gang, will be arraigned in Massachusetts on a slew of charges, including 19 counts of murder.

But according to Buchanan Ingersoll & Rooney White-Collar Shareholder Barry Slotnick, the hundred plus-page indictment may present a challenge to the government.

"The crimes are so old, the proof may be difficult," Slotnick explained to Bloomberg News. "Are the witnesses still around? Are they still available?"

Bulger faces life in prison for a 1995 racketeering indictment, but could receive the death penalty if convicted in state murder trials in Florida or Oklahoma.