Brad,
 
I'm not sure what you learn in the 5th grade.  I think it is sequencing of tenses that is the root of this "onry diffugalty," but it comes later, doesn't it? 
 
"By the time I'd finished paying for everything he had broken, I didn't have any money left to buy anything I needed." 
 
Breaking this down into propositions; a sentence for each clause:
 
1. He broke some things.
2. I finished paying for every one of these things at some time.
3. I needed some things.
4. I didn't have any money left to buy any of these things at that time.
 
Conceptually there are four points or periods of time being referred to: 
1) the period of time of the breaking,
2) the point of time of the finishing of payment,
3) the period of time of the needing, and
4) the period of time of not having money left.
 
The times relate to each other on a time-line:
(1 - - - > 1)(2)(4 - - - - >
(3 - - - - - - - - - - - - - >
 
The past tense of 3 is embedded in 4 as a relative clause and so shares its tense. 
Both 1 and 2 occurred at times previous to the time of 4 and thus also past tense. 
2 is embedded in 4 and occurs previous to it.  
1 is embedded in 2 as a relative clause and would thus share its tense. 
 
To some English users the relative previous time signals a need for agreement and the use of the perfect aspect.  The effort has been to make sure that (1) and (2) of the temporal clause are both in the same aspect as well as tense.  Perhaps the author (or editor) should have considered indicating the aspect in (2) and leaving (1) alone:
 
"By the time I'd finished paying for everything he broke, I didn't have any money left to buy anything I needed." 
 
However, I think that to you and more sophisticated users the time periods are perfectly clear without having to be explicit about it.  The description of the situation would be more alive without the aspect being expressed at all.  The discourse moves perfectly clearly from one event to the next without having to use aspect to explicate the relative times involved:
 
"By the time I finished paying for everything he broke, I didn't have any money left to buy anything I needed." 
 
Does this mean that using the perfect aspect is incorrect?  The cartoon author (or his editor) seems to have lost sight of clarity by hypercorrecting the more straight-forward writing.  Is spontaneity what you teach your fifth graders -- the grade that this author needs to repeat?  Better than repeating the 5th grade, perhaps a refresher course in correct grammar (use of tense and aspect markers) would be advisable. 
 
I'm not sure that Voltaire would be very well received in today's world, by the way.  I do not believe it's a question of being right or wrong.  Authorities (such as Voltaire himself) are certainly to be denied where they can be shown to be misleading.  I think authorities are best quoted to show respect for experience and understanding.  If those qualities are missing or not helpful in the authorities, the facts should speak for themselves, which they must in any case.  Perhaps we can quote Voltaire here to show that authorities such as he cannot be trusted with such sweeping generalities.  I feel that to rule out the use of the past perfect aspect out of hand is one of those sweeping generalities that we should be very cautious of. 
 
Bruce
 
 

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