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Answer: There are different types of triggers for Shehecheyanu: cyclical mitzvot, holidays, and fruit (Shulchan Aruch, Orach Chayim 225); acquisitions of significant objects (ibid. 223); finding out good news (mainly, ibid. 222). In your question, you use the latter two interchangeably; we will separate them.
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Because good news (ibid. 222:1) and bad news (ibid. 2) are very broad, the beracha trigger must elicit strong feelings. Most types of Shehecheyanu, according to most, are not obligations, but are voluntary and recommended when applicable (see Rama, OC 223:1; Mishna Berura 223:7). In cases where it is unclear whether they are warranted, most poskim (see Mishna Berura 223:12) apply safek berachot l’hakel (refrain when in doubt); some say it does not apply to such a subjective beracha when one feels the urge to recite it (see Tzitz Eliezer XIV:67). The above may explain what the Mishna Berura reports – most people do not make berachot over good and bad news. (The minhag is that one recites Dayan Ha’emet as a full beracha only for the death of a close relative – see Mishna Berura 223:8).
One could solve beracha l’vatala questions by combining it with a Shehecheyanu on clothing (Shulchan Aruch, OC 600:2) or by omitting Hashem’s Name. However, people have the right and maybe should (see Mishna Berura ibid.) make the berachot according to the opinions that when there is true happiness from good news (and sadness from bad), one makes a full beracha. This can include a variety of significant financial events (see Mishna Berura 222:1). However, your clients should be consistent. Take a real estate agent who does not make Shehecheyanu when he makes a sale. Should he recite it only when his fee was questioned, and he wins the same amount of money in adjudication?! In fact, as a dayan, I see several reasons why a ruling in adjudication should not bring on Shehecheyanu or Dayan Ha’emet.
Many rule not to recite Shehecheyanu on a fruit that was grown in a forbidden manner (see Yabia Omer V, OC 19) – that is not supposed to make you happy. Adjudication at times includes aveirot, e.g., going to a secular court; lying or misrepresentation; improperly insulting one’s "opponent." If one thereby received money he did not deserve, there should not be a beracha. If one lost the case, he should usually assume he deserved to lose, in which case Dayan Ha’emet is not appropriate, as he did not really lose anything.
In cases where one side is clearly right, the ruling reveals the obvious; it is likely different from the Mishna Berura’s (ibid.) retrieving property from a thief. If both sides have strong logic, making the ruling significant, one could factor in that his good fortune is at the expense of another, who is now upset (compare to the Ra’avya, Shabbat 289, who says not to make Shehecheyanu at a brit because of the baby’s pain).
There are other complications. In many cases, rulings include elements of winning and losing for both sides. Also, timing is not simple, considering that one: receives a ruling, there is time for appeal, and receiving payment can be a process (see Aruch Hashulchan, OC 223:4 on not making Shehecheyanu at a wedding).
I have not seen classical poskim suggest these berachot for adjudication, and the minhag is not to do so. Finding a different way to thank Hashem, and contemplating how to be a most moral litigant or not be one at all, may be wiser than solving a halachic doubt by including a new suit.
Lessons
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Shlach Lecha "Why So Many Don't Make Aliya?" - Parshat Shlach
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Kuzari -Rabbi Ari Shvat Kuzari class 2
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based on ruling 83033 of the Eretz Hemdah-Gazit Rabbinical Courts
based on ruling 83033 of the Eretz Hemdah-Gazit Rabbinical Courts

















