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There is no pressurized oil going through the head gasket. A leak that allowed draining oil to enter the coolant via the head gasket would also allow coolant to enter the oil. Usually.
A cracked head could pass it either way.
A cracked block might be more prone to a "one way" leak.
How much oil is he getting in there? A trace or a ton?
If it's just a little brown sludge on the cap, try a little clean up or flush if you want and watch it. But if it's measurable amounts regularly, get your tools out....
Rezvani's Latest Post-Apocalytic Monster Is a Ford F-150 Raptor Underneath
Slideshow: Called the Fortress, the 850-horsepower pickup combines Raptor underpinnings with military-inspired features, survival equipment, and a starting price of $285,000.