Most perceptive, 8 letters
Most shrewdly informed, 8 letters
Most well-informed, 8 letters
Common sense, 5 letters
Hip, 5 letters
Perspicacious, 5 letters
Query from Captain Jack Sparrow, 5 letters
Shrewd, 5 letters
Shrewdness, 5 letters
Street smarts, 5 letters
Streetwise, 5 letters
The cognitive condition of someone who understands, 5 letters
Wall St. whiz, 13 letters
Wall Street whiz, 13 letters
Hip relative?, 10 letters