What’s Better - Giving Tzedakah With a Condition or Without?
Question
It is common for people to make a condition, saying: “If I manage to sell the apartment, I will give such-and-such amount to charity,” etc. Is it better to simply give charity without making it conditional, and thereby merit Divine assistance? And if it is indeed better to give without conditions, then why did Yaakov Avinu speak in such a way, saying: “If G-d will be with me and guard me, etc.”?
Answer
Shalom uVracha,
Chazal say that it’s Le'Chatchillah to give tzedakah on condition, for example, “so that my son will live,” meaning for a specific salvation. What’s important is that in your heart you truly mean to give it regardless, even if what you wanted doesn’t happen.
And regarding Yaakov Avinu, that’s not a proof, since this was before Matan Torah.
Source
Rosh Hashanah Page 4. Tosafot Ibid, Tosafot Pesachim Page 8.