Critics often accuse Jackson of simply being a cheerleader of causes, a person who favors style over substance. Despite his unflagging energy and devotion to his causes, many felt that he was devoted only to his own self-aggrandizement. "This is the long-term pattern of Jackson's politics. He has always sought to operate and be recognized as a political insider, as a leader without portfolio or without accountability to any constituency that he claims to represent" wrote political critic Adolph Reed Jr. in The Progressive. "PUSH ran as a simple extension of his will and he has sought to ensure that the Rainbow Coalition would be the same kind of rubber stamp, a letterhead and front for his mercurial ambition."

Despite the criticism he has faced, Jackson continues to advocate for the rights of the downtrodden and challenge others to move beyond adversity. In 1995, Jackson wrote in Essence magazine, "People who are victimized may not be responsible for being down, but they must be responsible for getting up. Slave masters don't retire; people who are enslaved change their minds and choose to join the abolitionist struggle.. Change has always been led by those whose spirits were bigger than their circumstances… I do have hope. We have seen significant victories during the last 25 years."

In November 1999, Jackson came to the defense of six high school students expelled for fighting in Decatur, Illinois. The Decatur school board expelled the students for two years for their involvement in a brawl during a football game on September 17, 1999. After being pressured by Jackson, board members later reduced the punishment to one year and agreed to let the students attend an alternative school. Jackson met with the board to try to reach a compromise that would allow the students to return to regular classes, but the board refused to waver. As a result, Jackson led a protest march at Eisenhower High School where he was arrested on November 16, 1999, and later released on bond. He was charged with three counts each of criminal trespassing and contributing to the delinquency of a child. A federal judge later upheld the expulsions. Jackson received his master of divinity degree from the Chicago Theological Seminary on June 3, 2000. He had been only three courses short of earning his degree when he left the school to work with a minister more than three decades ago. On August 9, 2000, President Bill Clinton awarded a Presidential Medal of Freedom to Jackson. The medal is the highest civilian honor and may be awarded only by a U.S.