Yehiel Yeshaia Trunk is known mainly for his literary criticism on Sholem Aleichem and his seven-volume autobiography, Poyln: zikhroynes un bilder (1944–53). His Khelemer khakhomim oder yidn fun der kligster shtot in der velt (The Wise Men of Chelm; or, the Jews from the Wisest Town in the World; 1951), as well as his other imaginative reworkings of Jewish folklore, received very little critical attention, perhaps because his Chelm stories went unnoticed among the many collections of Chelm tales for children. Khelemer khakhomim is a vast book of sophisticated tales that artistically fuse the different Chelm traditions with innovative plots and historical, linguistic, and cultural material. Using mostly formalist methodology, this essay analyzes the devices and materials constituting a process I call shtetlization, in which the Chelm of folklore is immersed with the spirit and qualities of the shtetl to create not a realistic East European Jewish town but a myth of it. Locating Trunk's work in its circumstances of writing, my conclusion explores Khelemer khakhomim as a means of commemoration of the lost world of the shtetl in the aftermath of the Holocaust.