The Hamodia magazine published a tribute to someone who died recently and the story highlighted his generosity specifically in how he provided tefillin to bar mitzva boys who couldn't afford them.
However, the story was very troubling on another level. The recipient of the tzedaka seemed to feel entitled to the gift and had no sense of shame in taking it and felt no need to try to do anything to avoid needing the tzedaka.
The story is as follows.
Reb Nosson was a middle aged single man (no wife no children) who made aliya from Brooklyn. He learned in a yeshiva with Reb Shlomo "a very chashuve yid, a tremendous talmid chacham and a real masmid". When Reb Shlomo's oldest son was approaching Bar Mitzva Reb Shlomo had no money to buy him tefillin. A few months before the Bar Mitzva Reb Nosson gave him an envelope full of cash, enough to buy the best teffilin.
The next year was his second son's bar mitzva and again he had no money for tefilin. "I had no idea whether Reb Nosson's generosity would repeat itself this time around and with little alternative I waited to see what would happen. And in fact a few months before the bar mitzva the same scenario reoccurred. The story repeated itself four more times."
As you can see from the story already from the second son he felt a certain entitlement. He simply waited to see what would happen if the money would appear. Was there really nothing he could do? Why didn't he feel the need to try something so that he wouldn't need to take Reb Nosson's tzedaka?
The story goes on. "When my fifth son's bar mitzva was approaching Reb Nosson had already taken ill and hardly came to Yeshiva. I wondered whether this was the end of his generosity to me. After all out of sight means out of mind, didn't it?
Well it didn't ..."
Can you believe it? Reb Nosson is dying, alone, childless, and his friend (Reb Shlomo) is worried that Reb Nosson won't give him money so that he can buy tefillin for his son? How selfish is that? In fact, Reb Shlomo says that he was out of sight of Reb Nosson and he was worried that Reb Nosson forgot about him. Imagine, the man had no children, he is dying, and his chavrusa for whom he has done tremendous chesed for doesn't visit (otherwise why does he consider himself out of sight?)???
Contrast this to the following story about the Brisker Rav (published in במחיצתם). R' Shlomo Lorincz (the author) was traveling in America when he got an urgent letter that the Brisker Rav was sick and needed to move out of his small dark and dank apartment for health reasons. R' Lorincz immediately went to a rich relative and got a check for $20,000 to buy the Brisker Rav an apartment. However, before taking the check he said that he had to check with the Brisker Rav. He sent a telegram explaining things, and the Brisker Rav immediately responded "absolutely not". When he returned to Israel he went to the Brisker Rav to discuss the matter. The Brisker Rav asked him, how could you even consider that? How could I walk in the street living in someone elses house?
What a difference, the Brisker Rav was embarrassed to take charity while Reb Shlomo not only took it not once not twice but 5 times, but expected to get it and felt entitled to it.
This is a very big issue in today's world. everyone feels entitled. Boys who get married feel entitled to get an apartment from the girl's parents. They feel entitled to be supported. Today's Yeshiva Bachur has no compunction and feels no shame to take things for free even if he could do it himself. The idea of נהמא דכיסופא (literally free bread), which means that Hashem put us on this world so that we could earn our עולם הבא so we wouldn't be embarrassed by being נהנה מזיו השכינה for free, is a completely foreign concept to today's Yeshiva Bachur.
See these posts
Bnei Torah and a sense of entitlement
Why are you turning into a schnorrer?
for a similar theme.