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Should we consider everyone better than us?
The answer is DEPENDS on what we are comparing. We also need to remember that in some cases we need to compare ourselves to God instead of to our neighbors.
Can all of those arguments be put in harmony?
The answer is YES. You listed 3 arguments (below) but this answer currently focuses only on the first two. Because this answer's explanation makes a critical distinction between what we are comparing, we need a more detailed source before we can harmonize the third argument.
Introduction
We need to be very careful NOT to compare things that the text doesn't ask us to compare. For proper interpretation context, I read the whole Question 161 from the Summa and the whole Chapter II from the Immitation of Christ (1886 translation). More modern English translation here.
The Preface of the 1886 translation says that George Stanhope adds "words, clauses, and even sentences, that do not alter the purport and order of the thoughts, but give more time for dwelling upon each link in the chain" and still preserves the spirit of the book. But I think this translation changes the meaning somewhat for your bolded quote, which warned me that I should better read the larger context:
For lowliness of mind, and not thinking of a man's self "more highly than he ought to think," is the most difficult, but withal the most profitable, lesson; and the preferring others before ourselves, is a point of true wisdom and high perfection. Nor ought our opinions of this kind to be changed, though we should see another guilty of some egregious folly, or very grievous wickedness, since we ourselves are men of like passions and frailties; nor can we tell how long our own virtue may continue unshaken. Remember then, that infirmities are common to all mankind; and so remember it, as to persuade yourself, or at least to suspect, that these are dealt to thee in as plentiful a measure as to any other person whatsoever.
I had to look up the dictionary to get the less common meaning of "frailty" which is:
imperfection or weakness of character; frailty implies a general or chronic proneness to yield to temptation
ANALYSIS of Aquinas's relevant text
HUMILITY (Question 161) is part of the discussion on MODESTY (Intro in Question 160), which in turn is part of Temperance. In Q160 Art.1, Aquinas says Modesty is for less difficult things to moderate compared to Temperance which is for concupiscences of pleasures of touch. There are 4 kinds of Modesty (listed below). HUMILITY is treating the first kind.
Movement of the mind towards excellence, moderated by HUMILITY which is opposed to PRIDE
Desire pertaining to knowledge, moderated by STUDIOUSNESS which is opposed to CURIOSITY
Body movements and actions, becomingly and honestly, whether seriously or in play
Outward show in dress and the like
Then he made the 2 distinctions, in both cases HUMILITY does NOT apply:
What CAN we apply Phil 2:3 to? There are 2 things that we can humble ourselves to them.
PARAPHRASE of Chapter II of Imitation of Christ
Section 1:
Section 2:
Section 3:
Section 4:
INTERPRETATION: digesting the data
Here's my interpretation for the last paragraph: Therefore, the perfect wisdom is to tune your attention to other's virtues. When you see your neighbor commits a serious crime, remember that both you and your neighbor share a common human frailty, namely the chronic proneness to yield to temptation. You can say that NOW you are better (since you didn't commit that crime) but your desire for knowledge will deem you more vulnerable than your neighbor for the reasons stated earlier. So it is best to ADMIT that at your current state (preferring knowledge to virtue/serving) you are much weakened, and to motivate you to seek virtues why don't you say to yourself "none is more frail than myself".
The previous chapter 1 and succeeding chapter 3 should also provide support for my interpretation in #5:
[Chapter 1 paragraph 3]: What good does it do to speak learnedly about the Trinity if, lacking humility, you displease the Trinity? Indeed it is not learning that makes a man holy and just, but a virtuous life makes him pleasing to God. I would rather feel contrition than know how to define it.
[Chapter 3 paragraph 7, emphasis mine]: A good and devout man arranges in his mind the things he has to do, not according to the whims of evil inclination but according to the dictates of right reason. Who is forced to struggle more than he who tries to master himself? This ought to be our purpose, then: to conquer self, to become stronger each day, to advance in virtue.
CONCLUSION
There is no conflict between Q161 and Chapter II since:
The main point of Thomas Kempis's chapter II is the danger of pursuing knowledge instead of virtues. It offers mortification exercises (below). Therefore we shouldn't take the quote out of context.
What both texts DID NOT SAY: It's a virtue to consider ourselves the greater sinner than our neighbor despite the facts of the case.
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Should we consider everyone better than ourselves?
The short answer is no.
Everyone encompasses a lot of people!
True humility will admit that there are both people better and worse than ourselves.
No matter what sins we may have committed, there is someone who has done worse and is a greater sinner.
Take Adolf Hilter for example. Are our sins equivalent to his. Priests have told me that many persons in the confessional expressed the idea that they believe that they are the worst person on earth. But this is just not true. There is always someone who is worse than ourselves.
Are there any Judas Iscariots amongst us?
The saints have often considered themselves the greatest of all sinners. The fact is, that the closer we are to God the greater the reality of sin is and of our own sinfulness and need to be redeemed.
“Poor men and women who are sinners, I, a greater sinner than you…” St. Louis de Montfort from the beginning of his book The Secret of the Rosary.
This great saint of the Holy Rosary chose to address men and women by stating that he was a greater sinner than they were; which is interesting because we can honestly conclude that he was quite a holy man here on Earth and that he is now in heaven because he has been canonically recognized as a saint by the Catholic Church and thus is truly known to be in heaven.
To add to the gravity of the proposition that St. Louis de Montfort was the greatest sinner, I want to point out that being canonically recognized as a saint by the Catholic Church means that there was a thorough investigation done into his life and writings to prove that he lived a life of heroic virtue, including an investigation by someone called the Devil’s Advocate (hence the name of the term) who tries to prove that this person did not live such a life. If the person passes this test, then there has to be two scientifically unexplainable miracles that have to be investigated by a number of scientists; and the miracles must have occurred because of the potential saint’s intercession to God. - Why The Greatest Saints are Also The Greatest Sinners
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I would also answer, "no." I follow the Dominican tradition of truth. It is easy to see that if everyone esteems others to be better than themselves, then everyone (except one person) will be wrong. As St. Augustine says in the Summa article you quoted, "We must not esteem by pretending to esteem" (ST IIae IIae, Q. 161, A. 3, ad 2).
Secondly, even in the quote from your question, Aquinas is clear:
On like manner. humility does not require a man to subject that which he has of his own to that which his neighbor has of man's: otherwise each one would have to esteem himself a greater sinner than anyone else: whereas the Apostle says without prejudice to humility (Galatians 2:15): "We by nature are Jews, and not of the Gentiles, sinners." (ST IIae IIae, Q. 161, A. 3)
Note the terminus of Aquinas' reductio: "...otherwise each one would have to esteem himself a greater sinner than anyone else." Ergo, we do not have to esteem ourselves as the greatest sinner. We know this because St. Paul didn't do so in Galatians 2:15, where he pointed out that Gentiles are, ceteris paribus, greater sinners than Jews.
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St. Benedict's 7th degree (of 12) of humility (Rule ch. 7)
is, when, not only with his tongue he declareth, but also in his inmost soul believeth, that he is the lower (inferiorem) and viler (viliorem) of men, humbling himself and saying with the Prophet: "But I am a worm and no man, the reproach of men and the outcast of the people" (Ps 21[22]:7). "I have been exalted and humbled and confounded" (Ps 87[88]:16). And also: "It is good for me that Thou hast humbled me, that I may learn Thy commandments" (Ps 118[119]:71,73).
The Latin uses the the comparative inferiorem (lower) and viliorem (viler), not the superlative infimum (least) and vilissimum (most vile), respectively. He doesn't say we should consider ourselves the lowliest or the most vile. We are in a better state than those in hell, for example.