This question is a bit subjective depending on your view of the United State's current situation. However, looking to Theodore Roosevelt's point of view (based on his politics and ideology), we can make some assumptions as to what he would be thinking.
Theodore Roosevelt discusses many ideas that he has about the way to live life in his speech on "The Strenuous Life." He believes that, as a people, we should work hard and almost suffer in order to earn and provide for each other and this country. He believed in avoiding a life of ease and comfort, and he encouraged the American people would strive through difficulty and adversity in order to triumph.
Based off of this mentality, one can argue that he would be disappointed by the US's current political and social climate. It could be argued that today we live in a way which seeks comfort, quick solutions, and avoiding difficulty. This can be seen through the technological revolution of the past thirty or so years, and by the ideas that current politicians promote.
It would be good to avoid generalizing too much, but there is a certain level of subjectivity that comes along with this question. For more knowledge on this, look up his speeches for more details as to what he believed.