Before he was elected governor of Florida in 1998, Jeb Bush "often benefited from his family connections and repeatedly put himself in situations that raised questions about his judgment and exposed him to reputational risk," report Robert O'Harrow Jr. and Tom Hamburger in The Washington Post, noting that five of Bush's business associates have been convicted of crimes.
Bush, who cites his business experience to bolster his run for president, says that he was taken advantage of by unscrupulous businessmen and had no knowledge of wrongdoing. The Post found that Bush's intervention with federal officials helped one later-convicted fraudster get a government loan, and it opened its exposé with Bush's work with Florida company MWI, focusing on a trip he took to Nigeria right after his father was inaugurated in early 1989.
"My father is the president of the United States, duly elected by people that have an interest in improving ties everywhere," Bush told a group of Nigerian officials, while trying to secure an $80 million deal for water pumps financed by the federal U.S. Export-Import Bank. "The fact that you have done this today is something I will report back to him very quickly when I get back to the United States." He did, and President George H.W. Bush wrote a letter to Nigeria's president thanking him for hosting his son. MWI got the deal, and was later convicted on U.S. civil charges related to the Nigeria business. Jeb's speech was recorded, and The Post features it in this video on Bush's dealings:
Bush has never been convicted of any wrongdoing, and his moderate success (by his family's standards) turned into a financial windfall after he left office in 2007. He has given more than 100 speeches for $50,000 or more, and earned millions sitting on corporate boards. You can read more about his spotty business history at The Washington Post.