But records, lawsuits, interviews and newspaper accounts stretching back more than three decades present a picture of a man who, before he was elected Florida governor in 1998, often benefited from his family connections and repeatedly put himself in situations that raised questions about his judgment and exposed him to reputational risk.

Years after Bush’s visit to Nigeria, MWI was found to have made dozens of false claims to the U.S. government about its dealings in Nigeria, according to a civil jury verdict in a case brought by the Justice Department. MWI has denied the allegations and appealed the verdict. Bush was not a party to the lawsuit.

Five of his business associates have been convicted of crimes; one remains an international fugitive on fraud charges. In each case, Bush said he had no knowledge of any wrongdoing and said some of the people he met as a businessman in Florida took advantage of his naiveté.

Bush, now 62, has said that he has learned to be more careful about vetting his associates, telling the Miami Herald during his first, failed run for Florida governor in 1994 that getting “burned a couple of times” made him “better at deciphering people’s motives.”