- Despite having a very clean reputation, James Monroe did make a questionable decision during his time as a U.S. Diplomat in France. Tensions being high between Britain and France, the French wanted to ensure that the U.S. would not favor Britain and possible give them an upper hand. But the signing of the Jay-Treaty did just that, the French however did not find out about this agreement until weeks later, even though Monroe knew about it.
- During his first term Monroe met with sever Cherokee Chiefs to discuss the possibility of re-locating them out of Georgia. Monroe assured them with promise that they would never be forced to leave, but a mere two years later he forced all Cherokee's to move far south of the Mississippi