Question:


Answer: There are strict halachot about what can be done with the sales money of a holy article. The mishna (Megilla 25b) says that one must use the proceeds to buy matters of higher kedusha than that which was sold, which will not be of much help for you. However, the gemara says that if the city’s leadership in the presence of the population sells it, the money can be used freely. The Tur (Orach Chayim 153) says that, similarly, since every individual controls his property, he can sell it and use the money freely.
On the other hand, the gemara says that one may sell a sefer Torah only to enable him to learn Torah or get married. The Beit Yosef (YD 270) infers from the gemara’s and other sources’ use of the singular that it is referring to a privately owned sefer Torah, and still it is permitted to sell it only in very specific circumstances. The Shulchan Aruch (Orach Chayim 153:10) cites two opinions on whether it is permitted to sell, under normal circumstances, a privately owned sefer Torah (if a privately owned sefer was given over to community use the matter is more severe.) While there is not a consensus in deciding between the opinions, many have been lenient on the matter (see sources cited in Piskei Teshuvot 153:19).
Regarding the selling of privately owned tefillin the matter is significantly simpler. Besides the fact that the sanctity of a sefer Torah is higher than of all other religious articles, there is a special mitzva to write/possess one. Thus, if one sells his only sefer Torah, he may be uprooting the fulfillment of that mitzva, which is normally forbidden. However, if it was acquired in a manner that one did not fulfill the mitzva, then it is more likely to be permitted to sell (see Pitchei Teshuva, Yoreh Deah 282:16). Likewise, if one has another sefer Torah and thus will continue to fulfill the mitzva even after the sale, there are greater grounds for selling it (see Igrot Moshe, YD 163). In any case, the Magen Avraham (153:23) says that the prohibition for an individual to sell does not apply to holy articles other than a sefer Torah, such as tefillin. While not everyone agrees (see Be’ur Halacha to 153:10), the consensus seems to be to be lenient on the matter (see Shevet Halevi I, 41).
In your case, there are further reasons for leniency. Obvious it cannot always be forbidden to sell tefillin for normal profit, for if it were, what would a producer or merchant of religious articles do? The Beit Yosef (YD 270) says that for them, it is permitted because the holy articles were always slated for sale and not for their own personal use. The Kaf Hachayim (OC 153:90) takes this logic a step further. Since it depends on the owner’s intent when the article entered his possession, we check an inheritor’s intent upon receiving the tefillin. If he planned to use them for the mitzva, then the aforementioned questions arise about switching its designation and selling them. However, if, for example, he already had tefillin and wanted to sell them, then doing so would not be changing their designation and would be permitted. Since you fit into the latter category, leniency is even more strongly indicated.
While your financial situation is not our business, you may want to consider the following. If your financial situation is very difficult, it is possible that you need the money so that you can continue learning Torah with the regularity that you desire, which the gemara stated is justification for selling even a sefer Torah. If your situation is less dire than that, you may be one who gives significant tzedaka, and you may prefer not to sell your grandfather’s tefillin¸ but to do the following. Donate the tefillin to someone in need, and the money you save the poor recipient can be credited as your tzedaka, thereby lowering your out-of-pocket tzedaka expenses.