I must caveat upfront that I am not going to take a stance on whether or not you should let your kids participate in certain aspects of this traditional American holiday. I have found some Christians believe it to be a slippery slope, while others focus on redeeming the holiday. My focus is quite different. I’m remembering a specific evil that upset Jesus; not the overt imagery of horrors, but the evil that masquerades as good, especially within the church.
In Matthew 23: 1-12, Jesus instructs the crowd that though they were to listen to and observe the teaching of the religious leaders, they were not to do as the religious leaders did. Why? The religious leaders were merciless at holding people to burdens they could not bear. They were unsympathetic and insecure. These leaders’ “good” deeds were twofold: for show and for earning approval of men. They loved their titles and desired to be recognized as great men of God. As the Holman New Testament Commentary explains, these leaders had even fooled themselves into believing they were righteous.
While none of the imagery above would fit into a traditional category of Halloween, Jesus used imagery to describe these religious leaders, which goes well with today’s holiday. He said, “Woe to you, scribes and Pharisees, hypocrites! For you are like whitewashed tombs, which outwardly appear beautiful, but within are full of dead people’s bones and all uncleanness. 28 So you also outwardly appear righteous to others, but within you are full of hypocrisy and lawlessness.” (Matthew 23:27-28) Sure, on the outside, we may look the part of upright and moral Christians because we say this or dress like that, but what do our insides look like? Are we a spooky collection of rottenness on the inside?
To keep in line with the holiday terms, which is scarier: the evil imagery of decay and destruction that is obvious to the human eye or the evil ideology which presents itself as the good and beautiful, and therefore is not so obviously detected? Halloween traditions generally communicate evil for what it is: that which is not good. However, in our churches, and in our own lives, how much evil is masquerading as good?
Suggested resource: C.S. Lewis, The Screwtape Letters
“I live in the Managerial Age, in a world of “Admin.” The greatest evil is not now done in those sordid “dens of crime” that Dickens loved to paint. It is not done even in concentration camps and labour camps. In those we see its final result. But it is conceived and ordered (moved, seconded, carried, and minuted) in clean, carpeted, warmed and well-lighted offices, by quiet men with white collars and cut fingernails and smooth-shaven cheeks who do not need to raise their voices. Hence, naturally enough, my symbol for Hell is something like the bureaucracy of a police state or the office of a thoroughly nasty business concern.”
[From the Preface]
― C.S. Lewis, The Screwtape Letters
 Note: I use “generally” because it could be argued that some evil things, like vampires, in 21st century media are now being portrayed as good. As was the case with our own kid, we were cautious about her exposure to this kind of material until she was of an age to understand the themes represented of good and evil.
So......how do we handle Hypocrites?