Doing teshuva is hard work. Sinning can be fun, easy to do, financially beneficial and habit forming. Change is hard. It requires hard work, commitment, dedication and sacrifice. And such is when we are talking about changing our actions. Changing a character trait so that we will be less tempted to sin helping make our teshuva sustainable is so much harder. Becoming less materialistic, less anger prone, more generous and more compassionate takes years of hard work. And there are no guarantees of success. We must remain vigilant in our struggle with the yetzer hara.
“Come and hear: [for] shepherds, tax collectors, custom officials teshuva is difficult.” (Bava Kamma 94b) These are professions where, in Talmudic times at least, theft was most common. Shepherds would all too often allow their cattle to graze in the fields of others. Tax and custom officials might skim some money off the top and/or might collect more than the law required, pocketing the difference. Having stolen from the public at large it is next to impossible to know to whom to return the money. The Talmudic suggestion that they should involve themselves in communal work is only really a half measure as those who benefit from their work will not be the same people who were hurt by their theft. Sadly one who under declares their income cannot do complete teshuva. One does not know who was it that may have received less medical care due to budget constraints from those who paid less than their due in taxes. And even if and when the monies are paid back, different people will be the beneficiaries.
Recognizing how difficult teshuva can be our sages tried to make the process a bit easier. Perhaps too easy.
“Our Rabbis taught: thieves and those who lend money and charge [forbidden] interest who return [their ill-gotten gains] we do not accept it from them. And one who does accept it the Sages are not comfortable with him.” (Bava Kamma 94b) This is a rather unbelievable idea and seems to fly in the face of so many other basic teachings of Judaism. Is it possible that a thief is not obligated to return that which he stole? Can it truly be that the victim is forbidden to take back that which is rightfully his? Don’t the laws of teshuva themselves demand the return of the stolen goods? Yes, yes and yes. But no matter.
To help someone begin on the road to teshuva drastic measures are to be encouraged. The Sages realized that without granting thieves “clemency” they are unlikely to ever repent. It is very difficult to start anew with major debts hanging over oneself. Illustrating this the Gemara tells the story of “one who wanted to do teshuva. Said his wife to him ‘empty one, if you do teshuva even your belt does not belong to you.’ He held back and did not do teshuva.” (Bava Kamma 94b)
Yet allowing, nay insisting, a thief not pay back his money is so radical and so against the regular norms of the Torah that Tosafost claim such was a temporary emergency measure. The Tosafists interpret the comment of Rav Yochanan that this decree was enacted during the generation of Rabbi Yehuda Hanassi most literally insisting it applied during his generation only and none other.
Despite the cogency of Tosafost’s argument there is little evidence that such was enacted only temporarily. Most likely Rav Yochanan was stating the historical fact that such was enacted during the generation of Rebbe, but was not limited to it.
And thus the view of the Tosafists is rejected by the Rambam, Tur and Shulchan Aruch, the main codifiers of Jewish law.
While they may argue that the enactment still applies these authorities do greatly limit its application. For starters it only applies to professional thieves (or money lenders) for whom returning ill-gotten gains would literally bankrupt them. But for the occasional “white collar” theft no such exemption is in order.
Furthermore the exemption only applies if the object has been sold and one would have to pay its monetary equivalent. But if the object itself is still in the possession of the one who stole it, it would need to be returned.
Perhaps most importantly the exemption from payment only applies if one comes to do teshuva of one’s own volition. In such a case we bend over backwards to help, perhaps even refusing to let one pay anything back. But if the thief is caught and brought to court “kicking and screaming” no such leniencies apply. We help those who want to start a new chapter in life not those who want to continue in their sinning ways.
Our Sages looked to find the proper balance between making one pay for one’s actions and giving a helping hand to those who want to amend their actions. It is not an easy balance to find and one that may change from generation to generation. Yet by doing so to the best of our ability we are following in the path of G-d who “lends His hand to those who knock on the door of teshuva.”
 It is not by coincidence Abraham, Moshe and Dovid haMelech were chosen by G-d after having served as shepherds who resisted the temptation to let their cattle graze in the fields of others.
 The fact that there are infinite needs in the world does not mean one is obligated to pay more and more to solve all of life’s problems. There are limits to what one must donate. However once a government imposes a tax on its citizens avoiding one’s obligations makes one liable for stealing from the public – a sin for which teshuva is most difficult, perhaps impossible.
 With this enactment allowing the thief to keep his stolen goods the rabbis “passively uprooted something from the Torah”, akin to instructing us not to blow shofar when Rosh Hashanah falls on Shabbat. Additionally by invoking the principal of hefker beit din hefker, that the rabbinic courts can declare money ownerless, somewhat akin to the legal concept of eminent domain, the Sages can allow a debt to go unpaid.
 Most likely Rav Yochanan’s statement is not the reason for Tosafost’s view but serves as proof to their view that this can only be a temporary measure.
 As to why specifically his generation needed such an enactment Tosafost is silent. Perhaps we may suggest that his generation was one of great upheaval, one that feared for the future of Judaism. It was this fear that led him to commit the Oral Law to writing, something that also violated the norms of Torah. Perhaps in such a climate theft was rampant and the need to bring people back to the fold great. If anyone has any evidence to prove or disprove my speculative theory I would be most grateful.
 The Torah requires that one return the stolen object itself. Paying cash equivalent is not the same especially when dealing with personal items. Thus in any event one who returns a monetary equivalent does not fully fulfill the Torah’s mandate to return the stolen object.
In theory one who steels a beam and uses it in the construction of his home must “tear down” the home so that they may be able to return the beam itself. Recognizing how unlikely it is that one would be willing to do so – teshuva has its limits – the rabbis allowed, or more likely obligated one to pay money instead.