Depends. On how much, on if he is willing to do rehab, on if he pleas out on a lesser offense or less sentence, depends on the local (state/regional laws) when it comes to the class of drug in question. I think class D is usually pot,and Class E is something like codeine or vicodin - a prescription medication with a controlled substance in it. Legally the DA may be preparing to stick him with more charges in addition too the simple possession - perhaps a conspiracy to sell/traffic or an attempt to sell/traffic - depends on how much he had. As for the class E (if it is based on a controlled prescription medication) there may be other charges attached depending on how he came to get the drug - for instance if he stole it from someone. 95% of all cases heard in the USA are settled during preliminary hearings - they do not go to trial, instead the lawyers come up with a plea bargain which is usually a lesser sentence of a similar charge or in the case of multiple charges it is only one charge with the optimal or minimum sentence structure of that one charge. Other things that will affect the outcome are: If he is employed. If he has a family to support. If he is now or will soon be entering rehab/AA/NA/ or any other program of addiction recovery. The more 'yes' he has on being a 'upstanding member of society' the less his charges will be. Already having a history of possession of a controlled substance will lessen his chances at getting off 'lightly' Probation. However if he is willing to work with the system he might still get one more chance. If he does get 'one more chance' this will be his last one. The next time he will get hard time and little mercy.