The most common and most likely answer to this crossword clue is the 2 plus 5 letter word AT WORST
I've seen this crossword clue in The Guardian
A
T
W
O
R
S
T
More clues leading to the result AT WORST
- Dodgy two-star, taking the most pessimistic view
- Taking most unfavourable view of opener, conclusively stumped on a pair
- 8’s not begun, surprisingly, with glass completely empty?
- Taking the most pessimistic view, a team’s leader before defeat
- Two-star resort in the most awful condition
- Two-star novel taking the most pessimistic view
Buddy explains!

The straight part
We know that "with glass completely empty" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case with glass completely empty = at worst.The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.