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Answer: Refuah shleima! It is important to realize the nature of the practice of ma’aser kesafim. Tzedaka is a mitzva from the Torah, but its practical parameters are hard to define and quantify. Maa’ser kesafim gives a moderately ambitious (depending on a person’s circumstances) tzedaka formula (compare Rambam, Matanot Ani’im 7:1 and ibid. 5). In general, there are three opinions as to whether the practice of ma’aser kesafim is a mitzva from the Torah (Tosafot, Taanit 9a), a Rabbinic obligation (Maharil 54; Taz, Yoreh Deah 331:32), or a proper practice for one to accept (Bach, cited Taz ibid.; Shut Chatam Sofer, Yoreh Deah 231). The latter is the stronger possibility.
Most poskim rule that if one receives money as a gift and has freedom to use it as he likes, he is obligated in ma’aser kesafim (see Chikrei Lev, Yoreh Deah III:102). If the money is earmarked for a certain purpose, it is as if he received that matter as a present, and, according to many, he is exempt (see Tzedaka U’mishpat 5:(26)), especially if giving ma’aser kesafim will effectively preclude his obtaining that matter.
In your case, on the one hand, you can use the money for whatever you wish. However, medical expenses are primarily necessities one cannot reasonably ignore. One can suggest a proof that ma’aser kesafim does not apply to damage payment’s that relate to medical expenses (=ripuy). Ripuy is intended and calculated so that medical expenses should not harm the victim’s financial situation. It is conceptually optimal for the damager to directly arrange medical services for the victim rather than give an estimated lump sum of money for past and future expenses (Bava Kama 85a). Lump sum payments, when done, are a matter of practicality and convenience. If one had to give ma’aser on those payments, he would sustain a net 10% loss, and we do not find halachot of adding 10% to ripuy to cover the ma’aser. (One can deflect the proof on technical grounds, arguing that the obligation to pay damages is a Torah law, which does not take the victim’s worthy tzedaka practices into account, especially assuming they are Rabbinically-mandated or less. We would counter that the practice of ma’aser kesafim/tzedaka does consider the fact that ripuy is not general profits but necessarily earmarked payment, which it would be wrong to "tax."
In most cases, it is possible to at least approximate the breakup of the elements of large lump sum payments based on an itemized insurance claim or a court or arbitrator’s ruling). Major injuries can include loss of income, which should (halachically and legally) be compensated for, and here, the halachic logic is different. Since such payments are in place of earnings that that are presumed to be lost, this element should be treated as income, which is subject to ma’aser kesafim.
Bemare Habazak - Rabbis Questions (654)
Rabbi Daniel Mann
277 - Effect of Wrong Type of Bitul Chametz
278 - Ma’aser Kesafim from Proceeds of a Damage Suit Settlement
279 - “Ba’omer” or “La’omer”?
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Bemare Habazak - Rabbis Questions Ask the Rabbi: Forgot to Remove Tefillin Before Musaf of Rosh Chodesh
Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
Rabbis in Midrash
Lessons
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Kuzari -Rabbi Ari Shvat Kuzari class 9 - "Seeing is Believing" (parag. 21-30)
These paragraphs elaborate on the theme that seeing and knowing is better than any attempt to prove logically, and begins explaining the difference between Israel and gentiles.
Ein Aya Various Universal Stages of the Geula Process
Rav Kook examines the various stages of redemption, explaining how (in addition to the obvious oft-mentioned stages of ingathering the exiles, reviving the Hebrew language, army, state etc.) the messianic dream of world prosperity, the State of Israel and world unity can and are realistically and logically gradually coming true.
Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
How do we know that the "claim" of mass revelation to 2,000,000 witnesses at Mt. Sinai is really true? This important class answers all of the questions skeptics ask about this claim of the Kuzari.
Ein Aya Armies Still Necessary for Balance & the War Against Wars
Rav Kook explains why the world was originally divided into the various seemingly contradicting ideologies and cultures, in order to develop each one respectively. Swords or armies symbolize how each respective ideology defends themselves, as well as deters their opposing ideologies and cultures. On the other hand, the messianic era will be one of peace, and Rav Kook explains the transition to that stage, which mankind is already undergoing.
The Land of Israel LGBT'S IN ISRAEL
The question was asked, how can one make Aliyah with the LGBT parades?
Kuzari -Rabbi Ari Shvat Kuzari class 7 - Five Accumulative Proofs of G-d
As a preparation for the Kuzari's classic proof of G-d from the mass-revelation at Sinai, we start here with 5 other directions to strengthen our belief which also contribute to what the Kuzari will present as well.
Ein Aya Muscle & Meaning: The Dual Nature of Gevurah (Physical Strength)
Is physical strength and fitness a necessity or an ideal? Although it if often totally overlooked among topics of Judaism, Rav Kook writes that it clearly is also a necessity to deter the many enemies of Israel, but even in Y'mot HaMashiach, in the Messianic era, to a certain extent, it's ideal continues even after our enemies will have been finished off.
