I don't know how the World Press Freedom measures things, but the US has a totally free press. I don't see how it could be any more free, so I don't see how it can be less free than another country's, including African ones.
As for the Democracy Index, the US has democratically elected Trump, for better or worse. Trump's executive orders are also within the democratic framework. We might not like them, but all previous presidents have also used executive orders freely. US presidents have always had that power. They're much easier to undo than laws that have been pushed through Congress.
The Constitution has a set of checks and balances written into it so that no one branch of the government is more powerful than the other. The president can’t use an executive order to sidestep those checks and balances, and the president can’t take over powers from other branches, such as the power vested in Congress to pass new statutes or in the courts to invalidate certain laws as unconstitutional.
Many orders do not have any impact until a government agency takes some additional steps. Very often, an executive order requires a federal agency to write a report, undertake an investigation, or promulgate a new regulation. Those steps can often take months, and sometimes years.
There is nothing undemocratic about the US. Not liking the politics and actions of the president that was democratically elected does not equal the country being undemocratic. So I'm taking the Democracy Index with a pinch of salt, I'm afraid. I spend a lot of time in the US and I'm perfectly free to say what I want against the government without fear of retaliation, I have the freedom to carry a gun if I want (I don't, but not the point), and I can make any protest I want, as long as I do it peacefully without hurting others or property. I have 100 percent freedom in the States, as does everyone else who lives there.