If the judge set conditions on the dismissal, like paying the costs and doing community service, then the case is not dismissed until all conditions are met. His attorneys know that, it's just attorney bullspit.
As I understand it, he can’t be tried in State court ever again for any charge that were dismissed. He can however be tried in Federal Court for different Federal charges The pending civil lawsuit is not double-jeopard since its civil, not a criminal proceeding. Just like OJ was sued in civil court, the City of Chicago can in essence sue for damages.