One of the most progressive laws commanded in the Torah was that of yovel – the Jubilee Year – when all Jewish slaves were set free, and fields that had been purchased returned to their original owners. The Mishna (2a) teaches that the yovel begins on the first day of Tishrei, which, our Gemara points out, seems to contradict the simple reading of the Torah. The pesuk – see Vayikra 25:9-10 – commands that the blast of the shofar announcing the Jubilee year – together with the freedom of slaves and the return of land – should take place on Yom Kippur, the tenth day of Tishrei.
In answer to this question, the Gemara introduces us to the teaching of Rabbi Yohanan ben Beroka, who rules that the holiness of the yovel year begins on the first of Tishrei but that its regulations only take effect later on. Thus, beginning with the first of Tishrei, slaves no longer work for their masters, but they do not yet go home; rather, they eat, drink and rejoice, wearing their crowns. On Yom Kippur the shofar announcing the Jubilee year is sounded, and the newly freed slaves return home.
Rashi understands the ruling that the slaves sit “with crowns on their heads” as indicating that they are now free men who can wear crowns should they choose to do so. A similar idea is expressed by the Ritva, who explains that it is an expression indicating that the slaves can now behave like free men. The Meiri, however, quotes the Talmud Yerushalmi (our version of the Talmud Yerushalmi does not include this) as saying that this refers to covering the head with a sudar – a scarf or turban – which was the style of free men, not of slaves. This expression of freedom is one that we refer to daily as part of our morning prayers in the berakha of oter yisrael betifarah – thanking God for covering us with glory.
Historically, it is interesting to note that during the times of the Mishna, it was commonplace in Roman society for the free men to wear olive wreaths on their heads during times of celebration, something that a slave could never do. The week and a half between Rosh HaShana and Yom Kippur is described by Rabbi Yohanan ben Beroka as days of celebration, and it is certainly possible that the popular celebratory wreaths were worn by the former slaves on that occasion.