Winning,” football coach Vince Lombardi once said, “is not a sometime thing; it's an all the time thing.” Chuck Colson was not much good at football, but he was good at winning. He puckishly turned down Harvard, excelled at Brown, became a Marine, worked for the Assistant Secretary of the Navy in procurement, had three lovely children, practiced lucrative law, and capped it all off by serving his country as Special Counsel to President Richard Nixon (1969-73).

This was an impressive winning streak, and he did it all by age 38. As a young man, Colson had already stockpiled a lifetime worth of achievement. In his black Brooks Brothers suits, he fit the profile of the classic D. C. powerbroker—young, influential, and untouchable. Until he wasn’t.

‘I Would Walk Over My Grandmother’

Colson played hardball. During his time in Nixon’s administration, he targeted the President’s enemies, at one point spearheading a smear campaign of Daniel Ellsberg, leaker of the “Pentagon Papers.” The staffer became known as “Nixon’s hatchet man,” a sobriquet that followed him the rest of his life.

The hatchet man did not know it all, though. When Bob Woodward and Carl Bernstein published their Washington Post story about the break-in at the Watergate hotel in June 1972, Colson learned about it through the very same paper. Further revelations about Nixon’s team followed, including the taping of presidential conversations. Taken in concert with the Watergate burglary, this news drove public outcry against the President to fever pitch.

At this perilous time, Colson affirmed a reporter’s characterization from a week-old story: “Last week’s UPI story that I was once reported to have said that ‘I would walk over my grandmother if necessary’ is absolutely accurate.” This bold self-description would come back to haunt Colson in spades—and it helped end his prodigious winning streak.

In the summer of 1973, with the press still simmering over Watergate, Colson drove with his wife, Patty, to the Massachusetts coast. He visited a friend named Tom Phillips, CEO of Raytheon. In conversation with Phillips, Colson attempted a meager defense of himself. Phillips would have none of it. “If you had put your faith in God, and if your cause were just, he would have guided you. And his help would have been a thousand times more powerful than all your phony ads and shady schemes put together.”

Thrown off balance, Colson listened as Phillips read C. S. Lewis and shared the gospel with him. His simple testimony crashed into Colson’s defenses. After leaving his friend’s house, Colson began weeping so hard that he could not drive. He was undone, in the language of Isaiah, and he cried out to Christ for forgiveness. Against the odds, Chuck Colson had become a Christian.

Little did he know how much he would need his newfound faith. Not long after this moment, in July 1974, Colson stood before a Washington judge. He was sentenced to three years in prison. In September 1974, he entered the prison camp at Maxwell Air Force Base in Montgomery, Alabama.

Colson’s time in jail was not easy. The air was foul. At night, many fellow convicts struggled to sleep. He watched as inmates fought one another to no purpose, and he struggled to experience spiritual health in this deadened environment. In January 1975, Colson received incredible news: He was released from jail. He returned to everyday life and puzzled at his future. As he prayed, Colson could not shake an emerging, and surprising, conviction. He felt that he should launch an effort to help prisoners. You could say it like this: As soon as he got out of prison, Chuck Colson went right back in.

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‘Against the World for the World’

Colson threw himself into his newfound mission. He never went half-speed. As Michael Cromartie, Ethics and Public Policy Center vice president, told me, “Chuck thought like a Calvinist but worked like an Arminian.” Not many of the high and mighty would voluntarily—enthusiastically—return to the scene of their public humiliation to share the gospel with the malformed and forgotten. But Colson did.

Prison Fellowship formally incorporated in 1976. Initially, Colson funded it with royalties from his book Born Again. He soon added staff and initiatives. Justice Fellowship focused on prison reform. Angel Tree facilitated the giving of gifts to children of inmates. (President George W. Bush and his wife, Laura, participated in the program). The Chuck Colson Center for Christian Worldview, now led by John Stonestreet, enabled Colson to comment on cultural trends and featured the radio show BreakPoint, which over 1,400 stations carried by 2010. Colson worked closely with friends like Timothy George, Carl F. H. Henry, and David Dockery in this multi-colored tapestry of ministry. He and George co-wrote a popular Christianity Today column for several years. Everything Colson did, it seems, expanded.

Colson’s public-square work offers modern evangelicals a workable model. Initially, Colson considered himself contra mundum, “against the world,” as a believer. He wished to stand against evil. He never lost this vital perspective, but his friend, First Things editor Richard John Neuhaus, suggested Colson tweak the self-descriptor. The Christian, he said, is contra mundum pro mundo, “against the world for the world,” an elegant and accurate summation of evangelical engagement with a fallen order. The believer, and particularly the public-square witness, opposes evil, but does so not to defeat opponents or gobble up cultural territory. We are against the world out of love, seeking always to win lost friends to Christ and usher them into flourishing.

This is the key to understanding Colson. It differentiates him from the “culture warrior” label that is sometimes affixed to him. Colson was not a culture warrior; he was a Christian witness. In his mind, when he spoke against recidivism or postmodern amorality, when he created new projects to promote a united front against cultural decline, and when he talked quietly with a wayward person about the effects of sin and the reality of damnation, he was opposing evil out of love for neighbor. You could read Chuck Colson as an agent of the “religious right” or the “Moral Majority,” but in truth, he was in but not of these groups. Like his hero, William Wilberforce, he was against the world for the world.

What Victory Really Means

For all this work, Colson won the Templeton Prize for progress in religion in 1993. By the time his life ended in 2012, his investments had paid off. Amidst a panoply of projects, the core of Colson’s work was this: talking with prisoners about redemption. Over and over again, Colson entered prison cells and shared his conversion story. His hearers responded. The inmates of famously hostile Angola Prison so embraced Colson that they made a wooden coffin for him upon his death, as Colson's pastor Hayes Wicker revealed in an interview.

Some onlookers disliked Colson’s work and doubted his motives. One person who had every reason to do so was Bob Woodward, the journalist who had essentially ended Colson’s winning streak. In 2012, Woodward gave remarkable testimony to his transformation: “When Colson went to prison, he experienced, I think, a really genuine conversion and devoted himself to prisoners and prison reform. In a way you can’t question [him] because you talk to people in the prison reform movement and Chuck Colson is a god.” In the eyes of Woodward and others, Colson really had changed in the 1970s. Something had happened to him, something profound. Colson was not a “god,” but he met God. He was never the same.

Chuck Colson, like many a red-blooded American, loved winning. His understanding of success changed greatly during his life, however. It was only when he lost, and lost in spectacular fashion, that he tasted what victory really means.

Owen Strachan is the author of The Colson Way: Loving Your Neighbor and Living with Faith in a Hostile World (Thomas Nelson). He is a professor at Midwestern Baptist Theological Seminary.