When is pride a sin?

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It always is. Since nothing can, must or should be loved more than God.
 
The point to make is what we mean when we define pride. When we say things such as “I am proud of you” to a child who made the right choice, that is not sinful.

Pride in the sinful sense has been defined as:
desire to be more important or attractive than others, failing to acknowledge the good work of others, and excessive love of self (especially holding self out of proper position toward God).

So in my first example of being proud of a child, is to acknowledge the good work of others. Pride is the opposite of Humility, which is the acknowledgement that God is superior to man, and man is lowly and in submission to God. Man realized himself as he truly is, with defects, especially when compared to God.
 
From the Baltimore Catechism:
PRIDE - The inordinate seeking of one’s own excellence. It is opposed to the virtue of humility. It is the source of presumption, ambition, vainglory, and boasting.
From a teaching I once did on Capital Sins:
CAPITAL SINS: Pride
aka Perfectibility of Man, Progress, Prosperity Gospel, . . .]
Pride is the sin; the basis for all the rest. Pride puts oneself in place of God. It is the sin of Satan, and the sin of Adam and Eve. Pride states: I am the master of my fate; I am the captain of my soul.
Saint Paul reminds us that we have no basis for our pride. What have you that you did not receive? If then you received it, why do you boast as if it were not a gift? [1 Cor 4:7]

The Greeks feared Pride as Hubris; it is the precursor to destruction in their tragedies. The Book of Proverbs [16:18 ] says the same: Pride goes before destruction, and a haughty spirit before a fall.
Archbishop Sheen offers eight manifestations of Pride:
  1. Atheism, which denies our dependence upon God.
  2. Intellectual Vanity, which thinks it encompasses all knowledge.
  3. Superficiality, which judges others by their appearance, dress, wealth.
  4. Snobbery, which sneers at others to support its own superiority
  5. Vainglory, which seeks fame in the trappings of society.
  6. Presumptuousness, which causes one to value oneself too highly, to seek rewards rather than to make a contribution.
  7. Exaggerated Sensitiveness, To be unable to hear of ones faults.
Pride is an especially vulnerable point of one who would be holy. The Pharisees were holy men. However they focused on how far they had come; not on how far they had to go. The Pharisee gloried in his advancement over the Publican [Lk 18:9-14] and missed the call to go further.
Pride is also the vulnerability of the reformer. One sets out to improve the lot of the poor, but comes to believe that if one tries hard enough he can cure all the world’s ills. Heaven on Earth will come not from man’s efforts but by God’s action.
 
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