In 1988, in the dealings between his father and Michael Dukakis at the 1988 Democratic National Convention, Jackson's father obtained for him a position as an at-large member of the Democratic National Committee (DNC) by a nomination from Democratic Party chairman Paul Kirk.At the time, in Time magazine, Margaret Carlson depicted the younger Jackson as a well-spoken and compelling personality who would likely carry any of his father's political aspirations that his father was unable to achieve himself.
In October 2012, Jackson was investigated for financial improprieties including misuse of campaign funds.
While serving as the field director for the National Rainbow Coalition, he helped register millions of new voters through a newly instituted national non-partisan program.
He also created a voter education program to teach citizens the importance of participating in the political process.
Campaign controversy arose when it was revealed that Jackson's salary as field director the Rainbow Coalition had been subsidized by the Hotel Employees and Restaurant Employees Union, which was accused by a U. Senate investigative committee of having ties to organized crime.
Jackson was one of several Democrats who received campaign contributions from John Huang, a Democratic fundraiser who illegally funneled over 0,000 to Democratic candidates and was later convicted of conspiracy to commit campaign finance fraud.