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The gemarah in moed katan (28b-29a) records two statements regarding the experience of death either being as difficult as passing a (knotted?) rope through a hole [Rashi explains this refers to ropes uses in docking ships] or as releasing a cable through a hole [this chord is one holding two adjacent ships together] א"ר חנינא קשה יציאת נשמה מן הגוף כציפורי בפי הוושט רבי יוחנן אמר כפטירי בפי וושט

My questions are:

  1. How do these Rabbis know what death is like?
  2. Why did they choose this specific symbolism?
  3. Earlier the gemarah describes death as taking a hair from milk. The Maharsha explains the descrepancy with the former being the experience of the tzaddik and the latter that of the wicked. However this does not seem to be experientially true. What other explanation can there be?
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    Perhaps the Talmud is referring to the state of the soul, and its suffering or lack thereof, rather than the body. – mevaqesh Jul 28 '16 at 2:19
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    Rashi there explains the nautical symbolism a little (see this answer). – Fred Jul 28 '16 at 3:55
  • Your third question relates to a different passage - unless you combine it with this one, it sounds to me like it should be asked separately. Also, are you sure that you're quoting the right passage? How does ציפורי בפי הוושט mean a rope through a hole? Looks to me like it's referring to a bird (or something) through the opening of the trachea... – Shimon bM Jul 28 '16 at 11:35
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(How do you know this is not experientially true?)

Rabbi Mordechai Miller explained the greater the attachment the neshama has to the guf and its lusts, the more painful it is when it is seperated.

He gave an analogy of pulling a dressing from a wound when the scab has formed into the dressing.

It seems the chachamim had the sensitivity to quantify the pain of exodus from the body at the moment the neshama departs.

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    maasim b'chol yom. There are documented cases of righteous people suffering at death and wicked ones dying peacefully in their sleep. – rikitikitembo Jul 28 '16 at 2:17

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