1

The expression "an arrow in Satan's eye" is from the Talmud. What is the meaning of the expression "an arrow in Satan's eye?"

2

It's an expression that Peleimu used to say about the evil inclination as we see in Kiddushin 81a

פלימו הוה רגיל למימר כל יומא גירא בעיניה דשטן

In Steinsaltz Gemara it's explained as follows:

החכם פלימו הוה [היה] רגיל למימר** [לומר] כל יומא [יום]: גירא בעיניה [חץ בעיניו] של השטן, שהיה צוחק מפיתויי היצר.‏

The Sage Peleimu had the habit to say every day: An arrow in the eye of Satan, mocking the temptations of the evil inclination.

The same expression is mentioned in Menachot 62a with a similar explanation:

רב אחא בר יעקב ממטי ליה ומייתי ליה ומחוי הכי ואמר גירא בעינא דשטנא 

The Gemara relates: Rav Aḥa bar Ya’akov would extend and bring back the lulav in this manner, and would say: I am hereby shooting an arrow in the eye of Satan, as despite Satan’s best efforts, the Jewish people continue to fulfill mitzvot joyously

2

The meaning may vary slightly by context. In Kiddushin 29b-30a we find the following:

אמר רב חסדא האי דעדיפנא מחבראי דנסיבנא בשיתסר ואי הוה נסיבנא בארביסר הוה הוה אמינא לשטן גירא בעיניך

R. Hisda said: The reason that I am superior to my colleagues is that I married at sixteen. And had I married at fourteen, I would have said to Satan, An arrow in your eye. (Soncino translation)

Rashi there explains as follows:

כלומר הייתי מתגרה בו ושטן הוא יצר הרע ולא אירא שיחטיאני

That is to say, I would have provoked him – and Satan is the Evil Inclination – and it would not occur that he would cause me to sin.

Tosafot Ri Hazaken there (misatributed) writes:

חץ ומשל הוא

An arrow, and it is a metaphor.

R. Samuel Eidels writes:

וענין גירא בעין ע"ש שהעין תחלת סרסור דעבירה

[As for] the matter of "arrow in the eye", see there that the eye is the beginning of the agent of sin.

R. Yechiel Michel Epstein (Aruch Hashulchan E.H. 1:11) adds:

כלומר שהיצר לא היה מתגבר עליו כל ימי חייו

That is to say that the Inclination would have never overpowered him all the days of his life.

Jastrow, in his dictionary, translates the phrase as:

I should say to Satan I defy thee;

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