A German American from the South Side of Chicago, Pfleger attended Archbishop Quigley Preparatory Seminary South, Loyola University and the University of Saint Mary of the Lake. He was ordained a priest for the Roman Catholic Archdiocese of Chicago on May 14, 1975. Since 1981, he has been pastor of the mostly African American parish of Saint Sabina, a Catholic church in Chicago's Auburn Gresham neighborhood. His uninterrupted tenure in just one parish is normally unheard of in a diocese where pastors usually serve for only six to twelve years. When he was appointed to his present position, at age 31, he became the youngest pastor in the Chicago archdiocese. Under his leadership, Saint Sabina has established an Employment Resource Center, a Social Service Center and also an Elders home.
In 1981, Pfleger adopted an eight-year-old son, Lamar, in defiance of Cardinal John Patrick Cody, who had threatened to fire him if he went ahead with the adoption. Lamar graduated from college and got a job with Continental Airlines, which he lost after the September 11 attacks. He subsequently enlisted in the United States Army. In 1992, Pfleger adopted another son, Beronti, who attended the University of Central Florida before his sudden death on May 20, 2012. Pfleger says his son had been coping with an illness the past few years. In 1997, Pfleger became the foster father to Jarvis Franklin, who was killed by stray gunfire on May 30, 1998.
Pfleger's social activism has brought him media coverage throughout Chicago and beyond. He has often collaborated and associated with African American religious, political and social activists such as Jeremiah Wright, Joseph Lowery, Jesse Jackson, Harry Belafonte, Cornel West and Louis Farrakhan.
Under Pfleger's leadership, the community of Saint Sabina demanded the shutdown of a number of Auburn Gresham businesses specializing in drug paraphernalia. His parish also campaigned for the removal of tobacco and alcohol billboards from their neighborhood. When billboard owners refused to cooperate in the early 1990s, he and others decided to climb ladders and deface the signs. He was charged with destruction of private property, but was acquitted by a jury in 1991. In September 1997, the Chicago City Council voted 44–1 to eliminate tobacco and alcohol billboards from selected areas in Chicago. Pfleger described the decision as "a tremendous victory for the children of Chicago, for our neighborhoods, especially black and Hispanic neighborhoods."
Pfleger has become one of the best known critics of The Jerry Springer Show, a controversial television program which was videotaped in Chicago. Believing the program to be immoral, he and his parishioners began picketing outside the show's studios in 1991. By 1998, he had organized a boycott of the show's advertisers. "[Springer is] glorifying violence every day.... Calling a woman a ho and a bitch is sick. This is not normal behavior," he declared. The show's producers eventually claimed that they would attempt to decrease the number of on-stage fights on the program.
Pfleger later targeted radio personality Howard Stern in response to Stern's late 2005 advertising campaign to promote his move to satellite radio. Pfleger specifically objected to a pair of Stern's billboards in Chicago that featured an image of the black power salute with the caption "Let freedom ring. And let it be rung by a stripper" (a parody of a line in Martin Luther King, Jr.'s "I Have a Dream" speech). Pfleger told the media, "As we prepare to celebrate Dr. King's birthday, we will not tolerate this kind of disrespect. We should not have to tolerate it in our communities." Viacom, the owner of the billboards, eventually removed the signs because of Pfleger's protests. Pfleger received criticism from Stern's fans, who questioned Pfleger's commitment to freedom of speech. Jesse Jackson came to Pfleger's defense, saying, "There are two freedoms at issue here. They have the right to advertise, and we have the right to resist it in our community. Sometimes freedom is challenged by a community's tolerance level. I think Father Pfleger is a man of great dignity and has an acute social conscience. And he deserves our support."
In 2000, Pfleger received international attention for encouraging his parishioners to buy time from prostitutes as a means of inviting the women to counseling and job training. The Chicago Archdiocese largely distanced themselves from his efforts, to which he responded, "How is what I'm doing not part of the gospel? The church leaders talk about evangelization. Well, if this isn't evangelization, I don't know what is." Saint Sabina raised several thousand dollars for his program, attracting many donors from outside their parish. St. Sabina has used similar methods to reach out to drug dealers.
In 2001, Pfleger fired racism accusations towards a mostly-white primary school athletic league, the Southside Catholic Conference, after they refused to admit Saint Sabina's parish school. The league claimed that visiting teams and parents would be unsafe in Saint Sabina's neighborhood. He responded, "Racism continues to be alive and well both inside society and inside the church. To be denied admission on the sole premise that certain coaches and parishes feared for the safety of their children is illegitimate, ridiculous and insulting. It is very troubling that the conference would insinuate that we would place their children in harm's way." Chicago's Cardinal Francis George eventually pressured the league to reverse its decision.
In 2007, Pfleger and his Saint Sabina parishioners erected twenty billboards across Chicago with the words "Stop Listening To Trash", followed by a list of "disrespectful rappers", which included Fat Joe, Lil Wayne, Nelly, 50 Cent, G-Unit, Twista, Snoop Dogg and Ludacris. Pfleger said in a press release, "If we are going to end the violence and disrespect of women, we must fight every form of negativity, including the music industry." He explained to WMAQ-TV's Alex Perez, "When you disrespect women and you continue to demean a community or race by names and by language, that's unacceptable. ... We can kill with our words."
On March 28, 2008, Pfleger invited Jeremiah Wright, former pastor of Barack Obama, the former president of the United States, to deliver a blessing at Saint Sabina during a visit by poet Maya Angelou. Wright had been criticized by President Obama, academics and political pundits on the left and right for several controversial sermons, but Pfleger came to Wright's defense. "I wanted him to come here so he could see that people really stand with him and support him while he's under all this attack. America, unfortunately, has been really cheated of knowing the real Dr. Wright," said Pfleger. In a statement on Saint Sabina's website, Pfleger wrote, "Dr. Wright is one of the great biblical scholars of our country and the best of preachers in the prophetic tradition. Dr. Wright has been shamefully demonized by 30 second sound bites that have tried to re-define him into someone other than who he is."
In 2009, a documentary film called Radical Disciple: The Story of Father Pfleger was released. It was directed by Bob Hercules.
In February 2003, Pfleger generated controversy by inviting Al Sharpton to speak at a mass during Black History Month celebrations. Cardinal Francis George disapproved of Sharpton's appearance, due to Sharpton's pro-choice stance on abortion. Since Sharpton was a presidential candidate at the time, archdiocese officials were concerned that having a political candidate speak in church would cause them to lose their tax exemption. However, George decided that trying to stop Sharpton from coming "would be a futile gesture and a waste of effort".
Of his disagreements with George, Pfleger once said, "I can only assume the Cardinal sees my style of ministry to be something he doesn't agree with. In that sense, he sees me as a thorn. That's what I'm left to feel like. I don't revel in that. In fact, it's very difficult. It's a very difficult feeling [being] on the fringe, getting public reprimands, public criticisms. I don't enjoy that at all. [But] my focus right now is to try to continue building up the Church. A lot of what we do is [considered] out of the ordinary. That kind of puzzles me. It's not the Church I grew up in. The Church then was very involved in justice and civil rights issues."
In May 2007, during a Rainbow/PUSH Coalition protest outside a suburban Chicago gun shop, Pfleger was accused of threatening the life of the owner, John Riggio. The Illinois State Rifle Association released a tape where Pfleger was heard telling the assembled crowd, "He's the owner of Chuck's. John Riggio. R-i-g-g-i-o. We're going to find you and snuff you out… You know you're going to hide like a rat. You're going to hide but like a rat we're going to catch you and pull you out." Pfleger later claimed his use of the phrase "snuff you out" was misinterpreted.
Cardinal George rebuked Pfleger, saying, "Publicly delivering a threat against anyone's life betrays the civil order and is morally outrageous, especially if this threat came from a priest." Pfleger claimed that he did not intend to use the word "snuff" as a slang term for "kill", but rather as a substitute for "pull", as he used later in his statement.
During another protest at the same store, Pfleger and Jesse Jackson were arrested by Riverdale police for blocking the entrance to the store. Both were later released without charge. The store had been the target of multiple protests by Pfleger and Jackson. According to the Americans for Gun Safety Foundation, Chuck's Gun Shop & Range had sold over 2,000 weapons that were traced to crimes committed between 1996 and 2004.
On May 25, 2008, Pfleger gave a sermon at Trinity United Church of Christ, then Presidential candidate Barack Obama's church, where he made controversial statements concerning Senator Hillary Clinton, Obama's opponent for the Democratic Party nomination. Pfleger said, "I really believe that she just always thought, 'This is mine. I'm Bill's wife. I'm white, and this is mine. I just gotta get up and step into the plate.' Then out of nowhere came, 'Hey, I'm Barack Obama,' and she said, 'Oh, damn! Where did you come from? I'm white! I'm entitled! There's a black man stealing my show!'" He then pretended to wipe tears from his face, a reference to Clinton's emotional speech before the New Hampshire primary, and added, "She wasn't the only one crying. There was a whole lot of white people crying."
After hearing about Pfleger's remarks, Obama said he was "deeply disappointed in Pfleger's divisive, backward-looking rhetoric". Pfleger later released a statement through St. Sabina that read, "I regret the words I chose Sunday. These words are inconsistent with Sen. Obama's life and message, and I am deeply sorry if they offended Sen. Clinton or anyone else who saw them." On May 31, 2008, Obama resigned his membership in Trinity Church, saying that his campaign had caused the church to receive excessive media attention. On June 1, 2008, Pfleger released a longer apology to the St. Sabina parish regarding the incident and its aftermath.
On June 3, 2008, Cardinal George asked Pfleger to take a disciplinary leave of absence from St. Sabina. George said in a statement, "I have asked Father Michael Pfleger, Pastor of St. Sabina’s Parish, to step back from his obligations there and take leave for a couple of weeks from his pastoral duties, effective today. Fr. Pfleger does not believe this to be the right step at this time. While respecting his disagreement, I have nevertheless asked him to use this opportunity to reflect on his recent statements and actions in the light of the Church’s regulations for all Catholic priests. I hope that this period will also be a time away from the public spotlight and for rest and attention to family concerns." Pfleger resumed his parish duties on June 16, 2008.
On April 11, 2010, Pfleger delivered a 70-minute sermon in which he said the Apostles "had run out on" Jesus. "They had turned their backs on Him. They had left the One they had been with for three years, 24/7, and they ran away from Him when He most needed them. Only John, at the foot of the cross, and the women. That's why there should be women priests. That's why there should be married priests. That's why there should be women bishops and women cardinals." The Archdiocese of Chicago later issued a statement by Pfleger in which he apologized for his remarks but reaffirmed his support for women's ordination. Pfleger said on his Facebook fan page that he was told to apologize, despite still holding those opinions. Pfleger denounced critics of his comments as "ignorant haters" who took his homily "out of context" and used them “for their own particular motives”.
On Wednesday, April 27, 2011, the homepage of the website of the Archdiocese of Chicago released a statement from Cardinal Francis George in the form of a letter, temporarily suspending Pfleger from administering any of the sacraments (save for the administration of the Sacrament of Penance in an emergency, which even laicized or excommunicated priests may do) and from his active ministry as pastor of St. Sabina's Parish. George had recently suggested that Pfleger take the position of president at Chicago's Leo Catholic High School, but Pfleger said he would consider leaving the Catholic Church if forced to leave his parish. Cardinal George replied, in part, "If that is truly your attitude, you have already left the Catholic Church." Cardinal George lifted the suspension on May 20, 2011.