I would find it difficult to ever argue that the Trail of Tears was the right thing to do, morally, politically or otherwise. While, of course, the times were different and prejudice against Native Americans was nearly universal back then, the end result of the long march to Oklahoma was, quite simply, genocide.
In a legal sense, the Cherokee of the 1830s were full US citizens, assimilated, Christian, farmers and English-speakers. To rob them of their property and exile them to Oklahoma, not to mention killing nearly a third of them in the process was a criminal act. The Supreme Court of the United States, even in those racist days, declared the Indian Removal Act unconstitutional, yet Jackson went ahead with the forced march anyway. This makes it almost impossible to argue that ignoring the Supreme Court and killing citizens (not to mention humans) was in any way handling the issue correctly.
To me, the Trail of Tears is a stain on our national history.