His schooldays are irrelevant, it's about now & his use of convenient plausible deniability.

Raubgold

Here's a summary of Trump's reputation.

No words needed.

Bonfires blaze, the crowd delights,
While history’s ghost rewrites the nights.
They burn the man who dared to stand,
Yet steal far more with a careful hand.

The rule is not absolute for all personnel; special operations units may be able to request/receive exceptions for “mission-essential” reasons where blending in may be required. However, the exception is not automatic; it must be justified as mission-essential, which is ridiculous & unworkable.

TRUMPTON | EP 6 "The Mayor's Birthday"

Chippy Minton, wearing a suit that fits where it touches, gatecrashes the festivities.