Officially known as the Office of Counsel to the President and Vice President, this role was created in 1943 and is responsible for advising on all legal aspects of policy questions, legal issues, ethical questions, financial disclosures, and quite a bit more. With all that big responsibility, comes an even bigger check of $180,000 per year.
Although this role is to offer legal advice to the president and vice president, the counsel is in an official capacity without serving as an attorney for the White House. However, some amount of controversy has arisen due to attorney-client privileges.
Portrait Artist — $500,000
The White House portrait artist might not take down an annual salary, but they still get plenty of work, since they will often paint presidents, first ladies, vice-presidents, and second ladies. They are commissioned per portrait, and it's a weird gig.
President Theodore Roosevelt destroyed the first painting Theobald Chartrand presented, stating it wasn't masculine enough. For the Teddy Bear, that's a pretty easy mistake to make. President John F. Kennedy's portrait was done posthumously, so painter Aaron Shikler had to piece it together from photographs of Kennedy's face, and used his brother Ted as the body.
Chimney Sweep — $0
Yes, really. The White House has a lot of chimneys, and while they might be used less these days than when the structure was originally built, the big building still requires plenty of heating to stay warm during those cold East Coast winters. Jeff Schmittinger was the White House chimney sweep since he started in the Clinton administration. He refused to accept any money for the gig all the way up until his retirement in 2017.
He kept an old-fashioned chimney sweep costume in case someone wanted the full, classic experience. Jeff's website features a picture of him in full regalia, on the White House roof, holding an American flag.
Assistant to the President and Principal Deputy National Security Advisor — $180,000
It's not unfair to say national security is one of the more important tasks of the president, which is why the National Security Council is so stacked with members. The Principal Deputy National Security Advisor is responsible for being the Executive Secretary to the National Security Council Principals Committee and the chairman of the National Security Council Deputies Committee.
The role does tend to change depending on what is needed in the council. There are often numerous deputies – there's a lot of work to do. For all that work, this role commands the price of $180,000 per year.
Director of the Office of Administration — $180,000
The Office of Administration is within the Executive Office of the President (consider it a small division of a company) and is tasked with overseeing the general administration of the entire Executive Office.
Since 1977, it has overseen the administrative functions of the entities of the Executive Office, mostly by providing administrative services. It seems like the person who holds the role has a lot on their hands, but don't feel sorry for them as they earn $180,000 each year.