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The Kitzur Shulchan Aruch (119:10) writes:

מי שאינו שותה יין כל השנה מפני שמזיק לו, אע"פ כן צריך לדחק את עצמו לשתות ארבע כוסות, כמו שאמרו רבותינו זכרונם לברכה, על ר' יהודה ב"ר אילעי, שהיה שותה ארבע כוסות של פסח, והיה צריך לחגור צדעיו עד שבועות. ומכל מקום יכול למזגו במים, או לשתות יין צמוקים - עין לעיל סימן ו או שישתה מעד [מי דבש] אם הם חמר מדינה

This seemingly implies that although one may get a headache from drinking he should nevertheless drink wine. Does the Kitzur speak about 'Shavuot' figuratively for emphasis? Otherwise, I would imagine that if a person had a migraine for 7 weeks as a result of wine on Pesach he may be exempt?

The Shulchan Aruch (272:10) states that "A person who doesn't drink wine because it damages himself, or he dislikes it, needs to push himself to drink, to fulfil the obligation of the mitzvah of four cups". The Mishna Berura on this says that 'mitztaer' explicitly means a headache and not a bed-ridden ailment.

This seems to be speaking about a person with a predisposition to headaches from red wine. Why is the Torah obligation to drink four cups of wine so strong, in this instance, that you must deliberately place yourself into a situation of tza'ar?

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Its a Rabbinic Obligation –  sam Apr 23 at 21:58
    
The quote about shavuot is straight from the yerushalmi (pesachim 10 1). Note that they (in the days of the yerushalmi) didn't have grape juice so nowadays this isn't really applicable. Also in the original story he had the headache until sukkot. –  Double AA Apr 23 at 22:09
    
The kitzur himself mentions alternatives and brings this story of praise. his phrase 'yachol' could mean that he is advocating drinking wine regardless of if you'll get a headache until shavuot –  bondonk Apr 23 at 22:11
    
@DoubleAA See this comment. In my subsequent comment, I note the Korban HaEida whose interpretation of the Yerushalmi is contrary to that of the Kitzur: וכאיב ליה ראשו עד עצרת לכך הכשיר במבושל שאינו מזיק כל כך. –  Fred Apr 24 at 1:47

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