How should you start a leniency letter? Dear judge (name), I am writing to ask for leniency in the sentencing of my husband, because (then give all your reasons and speak only from your heart).I am writing this letter on behalf of a former student of mine who is presently before you on criminal charges and is due to be sentenced shortly. Address the judge respectfully. Briefly introduce yourself and your relationship to the individual. A character letter plays a dual role. I am writing this letter behalf of my dear friend Princewill Johnson. Mr. Princewill and I have been close friends over 10 years now. The core of your letter should explain why you believe the judge should show leniency towards the defendant. At the end of a character letter, most writers make an "ask" of the court.