Our Gemara on Amud Beis warns of various careless financial practices:

And Rabbi Yoḥanan says: In the case of one whose father bequeathed him a great deal of money and he seeks to lose it, he should wear linen garments, and should use glass vessels, and should hire laborers and not sit with them to supervise. 

A unique feature of this Talmudic passage is that it seems to be resorting to sarcasm. Sarcasm is a particular human style of communication that employs irony and indirectly communicates criticism and hostility. Often, sarcasm is a passive aggressive remark, made by those who do not feel empowered to express themselves directly.

If so, why would the Gemara resort to sarcasm here? 

There are other Jewish sources for sarcasm as well. Here is a brain teaser: Name two places in the Chumash that are sarcastic:

Kayin defensively responds to God‘s inquiry on the whereabouts of Hevel, “Am I, my brother’s keeper?” (Bereishis 4:9). 

When the Jews were in a state of panic, thinking that they were facing certain doom as Pharaoh’s army was closing in on them by the Red Sea, they sarcastically complained: 

“Is there a shortage of gravesites in Egypt that you had to bring us out to the wilderness to die?” (Shemos 14:11)

In both of these instances, the sarcasm and passive aggressiveness came from a feeling of being cornered, such as how Kayin felt when questioned by God, or how the Jews felt trapped. The powerlessness and fear allows aggression to come out only indirectly.

We must ask ourselves, then why would our Gemara need to resort to sarcasm? The Rabbis were providing a reasonable and important message, so why obstruct it with unnecessary sarcasm and irony?

There is some fascinating research, which seems to show that there is a social function for sarcasm, which actually can aid learning and creativity, notwithstanding the more frequent toxic effects of hostility and passive aggressiveness.

Researchers Huang, Gino, and Galinsky (Organizational Behavior and Human Decision Processes 131 (2015) 162–177, “The highest form of intelligence: Sarcasm increases creativity for both expressers and recipients”) studied the communication patterns and learning that occurs when ideas are expressed sarcastically. They found:

“Both expressing and receiving sarcasm, regardless of its content, can facilitate creativity by increasing abstract thinking. We also identify a factor, interpersonal trust, that helps reduce the relational cost of sarcasm for both parties but still allow organizations to take advantage of its creative benefits.”

Yet, the toxicity of sarcasm cannot be ignored: 

“Because sarcastic remarks often express the poisonous sting of contempt (Gottman & Silver, 1999), they can undermine relationships and harm communication in organizations. For example, Fredrickson and Losada (2005) analyzed 60 management teams and identified sarcasm as a form of negative communication among team members and an important cause of poor performance in struggling teams.”

In one study they cited, it was found that:

“When participants expressed sarcasm toward or received sarcasm from a trusted other, creativity increased but conflict did not. We discuss sarcasm as a double-edged sword: despite its role in instigating conflict, it can also be a catalyst for creativity.”

It would seem that the jarring, challenging and conflicting effect produced by sarcasm, can also inspire a certain degree of letting go of preconceived notions, reconsidering, and creativity. This might be similar to the process how on Seder night we do odd things in order to stimulate curiosity in the children, כדי שישאלו התינוקות (see Shulchan Aruch OC 473:7.) Artists use satire which also can be a form of sarcasm to the authorities and rigidly held beliefs. Sometimes it might be out of fear of persecution, and so it is done humorously indirectly (such as anti vax or election deniers who might perform songs on YouTube, in the hopes that they won’t be banned as “misinformation” because, after all, it is just a song.  Unfortunately, that did not work out well for Michoel Green.  Our media overlords do not tend to have a good sense of humor.) Other times, it might just be social critique done in a challenging and humorous manner to force people to confront themselves in a way the other otherwise might not.

Sarcasm might be analogous to tickling or other forms of intrusive discomfort that can either be seen as playful or disrespectful. Much of it depends on the intention and the trust in the relationship.