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execve("/usr/lib/valgrind/memcheck-amd64-linux", ["/usr/bin/valgrind.bin"], [/*
39 vars */]) = 0
open("/proc/self/maps", O_RDONLY) = 3
read(3, "38000000-381f5000 r-xp 00000000 "..., 100000) = 549
read(3, "", 99451) = 0
close(3) = 0
mmap(0x402001000, 4194304, PROT_READ|PROT_WRITE|PROT_EXEC,
MAP_PRIVATE|MAP_FIXED|MAP_ANONYMOUS, 0, 0) = -1 EPERM (Operation not permitted)
getpid() = 27233

When trying to start valgrind on grsec enabled machine. Any ideas why this fails?

It's the new MPROTECT behavior to reject RWX mappings instead of silently demoting them to RW. You'll have to turn off mprotect on the valgrind binary.

-Brad