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What is the history of Jewish bar mitzvah boys giving a Drasha/Pshetel? Is this a Minhag?

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It is a minhag. It is recorded by the Mishnah berura 225:5.

Based on this it seems to be about 400-500 years old:

The religious aspect of the bar mitzvah feast was enhanced in Poland, where the drasha was introduced. In Poland, the center of talmudic learning in the 16th and 17th centuries, there were precocious and highly gifted boys of bar mitzvah age who were capable of delivering an original casuistic discourse in talmudic law. Naturally, these boys were the exceptions, but there were many others who could, with the assistance of their teacher, accomplish this feat of learning. It was a test and display of talmudic knowledge. In many cases, the teacher prepared the drasha, and the boy learned it by rote and then delivered it.

The Kaf Hachaim 225:11 explains the reason for the drasha -

והטעם משום דבהתחלת שנת י"ד זוכה לבחינת נשמה כידוע וע"כ נוהגין לדרוש ולעשות סעודה ביום שנכנס לבר מצוה כדי שע"י עסק התורה ומצות סעודה שעושין לכבוד הכנסו למצוה יזכה לבחינת הרוח היותר גדולה במעלה וקדושה ואם אינו יודע הבן לדרוש דורשין לפניו ואם אביו יודע לדרוש הוא יותר טוב משאר אדם. ועיין בסה"ק חקי חיים שסדרתי שם קצת דרושים השייכים לבר מצוה ולהלבשת תפילין קחנו משם

The Mishnah berura says that the drasha can make the seuda in to a seudas mitzvah if it isn’t held on the exact day of his birthday.

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