The most common and most likely answer to this crossword clue is the 4 plus 5 letter word ROAD AGENT
I've seen this crossword clue in Financial Times
R
O
A
D
A
G
E
N
T
Buddy explains!
The straight part
We know that "Old highwayman" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case old highwayman = road agent.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.