<<Why would anyone in his right mind try to override a pilot who prefers to err on the side of safety?>>
Possibly because they have absolutely no clue about aviation operations.
A British Prime Minister flying out of Heathrow once made it clear to the crew that there were to be no delays. Once the PM was aboard the aircraft was to taxy out and take off immediately. Unfortunately, there was a 30 minute ATC delay... so we had the pilot taxy all around the airport for 30 mins and then take off as soon as he reached the runway. The VIP was most impressed with the expeditious service, despite wasting tons of fuel...
Remember - a lot of VIPs are brainless.