“Which is the road leading to the city?” asked Rabbi Yehoshua ben Chananya of a youngster sitting at a crossroads.

“This is the shorter one,” replied the lad while pointing to one road, “but it is longer. The other road is longer but shorter.”

Rabbi Yehoshua decided to take the first road, that had been described as the shorter one, but when he approached the city he found access to it blocked by gardens and orchards. He returned to the crossroads and challenged his young guide for suggesting the shorter road that had turned out to be the wrong one.

“But I told you,” replied the boy, “that although it is shorter in distance, it is longer in reaching your goal.”

The Sage was so impressed by the boy’s wisdom that he kissed him on the head and exclaimed, “How fortunate are you, O Israel, that all of your people, from old to young, are so wise!” (Gemara Eruvin 53b)

There are several explanations in the commentaries (Maharsha1 and Etz Yosef[2]) of how it was possible for this great Sage to misunderstand the directions of the youngster. What is perhaps even more difficult to understand is why this story is mentioned by the Gemara in this particular place?

According to one view, this episode illustrates how careful one must be in expressing oneself and in understanding nuances in the speech of others, both of which are discussed in the previous Gemara.

Iyun Yaakov, however, viewed this story as an allegorical introduction to the next Gemara that elaborates on the way one succeeds in learning Torah and remembering it. Torah is compared in several passages in Tanach to a road. There are people who aspire to be Torah scholars but are reluctant to invest the effort and make the sacrifices necessary for reaching their goal. They foolishly believe that there is a shortcut to reaching the “city” of Torah knowledge. Rabbi Yehoshua saw in his experience that the road that seems easier to travel is not the one that will lead him to his destination.[3] He therefore praised the youngster for teaching him a vital lesson in life and did not hesitate to record for generations that it was a mere lad who cleverly taught him this lesson.[4]



1. Rabbi Yehoshua ben Chananya misunderstood: This road is short and long – i.e. the shortest way, but lengthy; This road is long and short – i.e. the longest way, but looks short.

2. Rabbi Yehoshua ben Chananya misunderstood: This road is short and wide – i.e. the quickest route; This road is long and narrow – i.e. if a passerby comes in the opposite direction, the journey will be delayed.

3. This last explanation supports the notion of chazarah, reviewing one’s learning. Although it might appear longer it is actually shorter because one retains knowledge thereby facilitating subsequent learning. (Rabbi Daniel Levy)

4. Based on Rabbi Mendel Weinbach’s article “The Long Shortcut” in TalmuDigest from Ohr Somayach.