The use of since has more subtleties than I was aware of, and you have good reason to be confused, it also confused me
"Since" can mean:
1.from a definite past time until now
3.after a time in the past
So when saying "since 1982" could mean from 1982 onward, or from after 1982 onward. One being inclusive and the other being exclusive of the earlier time.
"Israeli air strikes against Syria 'biggest since 1982'"
Technically it's not necessary that there were bombings in 1982, that's just the time they chose as the beginning from which to measure. However it's implied that there were larger bombings in 1982 and that they were larger than the current ones. The following timeline would match the meaning of the sentence.
YEAR:--------------------------1977--------1982------------------1997-----------------------PRESENT
BOMBS DROPPED____ 100 tons___ 80 tons _______ 30 tons_____________ 50 tons
As would:
YEAR:--------------------------1977--------1982------------------1997-----------------------PRESENT
BOMBS DROPPED_____ 0 tons____ 0 tons _______ 30 tons_____________ 50 tons
The sentence "implies" that the 1982 bombings were larger, but that is not "technically" required.
"US trade deficit largest since President George W. Bush"
The following timeline would match the meaning of the sentence.
YEAR: ------------1999------------BUSH ERA---------------2012-------------------------NOW
DEFICIT: ____$900bn_______$700bn_________$300bn____________$600bn
as would:
YEAR: ------------1999------------BUSH ERA---------------2012-------------------------NOW
DEFICIT: ____$900bn_______$100bn_________$300bn____________$600bn
"X is the biggest since Y", is Y the high water mark?
No, not necessarily. Both sentences "imply" that Y is the high water mark, but that's not strictly necessary.
There's a point here that's really important that I hadn't consciously noticed before. This can be a great form of rhetoric to mislead people while not lying. I'll give you an example.
Let's just say we're talking carbon dioxide concentration in the atmosphere, and we say that CO2 concentration is the highest it's been since 1980. All of the following timelines would match that statement:
YEAR: ------------------------1970-------------1980-------------2000---------------NOW
CONCENTRATION(PPM): 200________ 400 _______ 100 __________ 200
YEAR: ------------------------1970-------------1980-------------2000---------------NOW
CONCENTRATION(PPM): 200________ 50 ________ 100 __________ 300
YEAR: ------------------------1970-------------1980-------------2000---------------NOW
CONCENTRATION(PPM): no_data ____ no_data ____ no_data ________ 200
As I said, generally speaking it means that 1980 is high point. But it doesn't have to mean that, which is why you have to be careful when hearing something like this. Also according to the dictionary definition I gave above it can be either inclusive of 1980 or exclusive. Strictly speaking this form of expression is saying nothing other than you've started the recording at an arbitrary point in time.