I don't know the glibc implementation, but in Doug Lea's malloc the answer is "no". Quote from the link:
> treat the wilderness chunk as ``bigger'' than all others, since it can be made so (up to system limitations) and use it as such in a best-first scan. This results in the wilderness chunk always being used only if no other chunk exists, further avoiding preventable fragmentation.
I guess there is one case in which the invariant could be technically violated: if the user allocated a chunk that was exactly the size of all remaining system memory.
There is a somewhat more in-depth discussion of how the wilderness should be managed in Wilson; Johnstone; Neely; Boles: "Dynamic Storage Allocation: A Survey and Critical Review", _Int'l Wkshp on Mem Mgt_ , 1995.