Jared Kushner, who serves as a senior adviser to his father-in-law, was skiing with his wife Ivanka Trump and their three children in Aspen, Colorado in the days leading up to Friday's vote. The family were photographed relaxing in the expensive resort.
Back in Washington DC, other members of Mr Trump's administration were trying to secure support for the President's draft American Health Care Act (AHCA).
Despite his Republican Party holding both houses of Congress and the US Senate, it was not put to a vote.
Speaker Paul Ryan persuaded Mr Trump to pull the measure on Friday, as it became clear it did not have enough votes to pass.
Mr Kushner did appear at the White House that day.
But a source told CNN that the President was "upset that his son-in-law and senior adviser was not around during this crucial week.”
A White House spokesperson denied the claim.
Although Mr Trump was able to avoid the humiliation of a defeat in house, it is widely seen as a failure for the President, who made repealing and replacing Obamacare a cornerstone campaign pledge.
White House press secretary Sean Spicer said Mr Trump “left everything on the field” in his efforts to get the bill passed.
Although it is not clear what Mr Kushner in particular could have done to help persuade Republicans to back the policy, Mr Trump may have been relying on his son-in-law and daughter for moral support.
Instead Ms Trump and the children took off for Aspen in Mr Trump's private 757 jet, accompanied by her brothers Eric and Donald Trump Jr, and Eric's wife Lara. They were later joined by Mr Kushner.