If in 2008 you had pondered the possibility of a winner-take-all matchup between president-elect Barack Obama and then Archbishop of Milwaukee Timothy Dolan, I think few would've considered it a fair fight.
As President-elect Barack Obama stood between the Greek columns delivering his acceptance speech, not only the country applauded but the world. There were few who weren’t moved. Barack Obama seemed to be a man astride the Earth.

One can look back now and say he was just reading off a teleprompter or that the Republican Party had nominated a candidate who was never really sure he wanted to beat Obama. One could even say that the image of Obama between the columns was a foreshadowing of the overreach that would lead to so many difficulties later. But all of that came later. Think of the man at that moment. All things seemed possible for that man, at that moment. Even his opponents were proud of what his election said about the country.

And now oppose this image in your mind with the then chubby amiable archbishop of Milwaukee who had little national notoriety at the time. To most culture watchers, he likely would've been classified as likable middle management of a increasingly irrelevant institution. Dolan's own diocese was awash in allegations of clergy abuse. In Dolan's own words, he was reportedly “haunted” by the scandal.

But let’s face it, if some fever brained Vegas mind created a matchup between the president-elect and the archbishop of Milwaukee, it likely would've been considered a warm up bout for Obama. An under card.
A little over a month after Obama’s inauguration, Dolan was appointed the 10th archbishop of New York by Pope Benedict XVI. Archbishop Dolan was known as an outspoken pro-lifer but not with the stick in-the-eye verbiage of others. In September of 2011, Archbishop Dolan he did issue a stern challenge to the Obama administration's decision not to support a federal ban on gay marriage, and warned the president that his policies could "precipitate a national conflict between church and state of enormous proportions."

Those were strong words but if anybody believed that Archbishop Dolan would be a force to be reckoned with in a any national conflict they would likely have been disappointed early on as Governor Andrew Cuomo pushed "gay marriage" through the New York Legislature in Dolan's back yard with relative ease.

Many Catholics wondered why Archbishop Dolan didn't put up a stronger fight. Even the New York Times wrote a piece, wondering where Dolan and the Church were on the fight.

"It was befuddling to gay-rights advocates: The Catholic Church, arguably the only institution with the authority and reach to derail same-sex marriage, seemed to shrink from the fight.

As the marriage bill hurtled toward a vote, the head of the church in New York, Archbishop Timothy M. Dolan, left town to lead a meeting of bishops in Seattle. He did not travel to Albany or deliver a major speech in the final days of the session. And when he did issue a strongly worded critique of the legislation — he called it “immoral” and an “ominous threat” — it was over the phone to an Albany-area radio show. Inside the Capitol, where a photograph of Mr. Cuomo shaking hands with Archbishop Dolan hangs in the governor’s private office, the low-key approach did not seem accidental. Mr. Cuomo had taken pains to blunt the church’s opposition.

When he learned that church leaders had objected to the language of the marriage legislation, he invited its lawyers to the Capitol to vent their frustration.

Mr. Cuomo even spoke to Archbishop Dolan about the push for same-sex marriage, emphasizing his respect and affection for the religious leader. An adviser described the governor’s message to Archbishop Dolan this way: “I have to do what I have to do. But your support over all is very important to me.”

By the time a Catholic bishop from Brooklyn traveled to Albany last week to tell undecided senators that passing same-sex marriage “is not in keeping with the will of their people,” it was clear the church had been outmaneuvered by the highly organized same-sex marriage coalition, with its sprawling field team and, especially, its Wall Street donors.

“In many ways,” acknowledged Dennis Poust, of the New York State Catholic Conference, “we were outgunned.”

In fact, Archbishop Dolan wasn’t even in town when the vote occurred. He later explained that what looked like apathy was the product of heeding bad advice. He later reportedly said,:

“We got burned last year when we were told the redefinition of marriage didn’t have much of a chance — and of course it did. Our Senate leaders, we highly appreciated them being with us all along. When they kind of assured us it didn’t have much of a chance — not that we let up, but we probably would have been much more vigorous and even more physically present if we knew there was a chance. … We got a little stung, and it could be as much our fault as anyone else’s."

That was an auspicious beginning.

But in July of last year, the brewings of a new fight started, a suddenly announced new front in the culture war.

The Institute of Medicine recommended that the HHS mandate coverage of surgical sterilization and all FDA-approved birth control in private health insurance plans nationwide. Everyone waited to hear what the religious exemption would be?

The thinking from the left is that there was nothing to be afraid of by going up against the Catholic Church. Who would possibly worry about being opposed to the Church after the decade the Church has had? Heck, the administration likely thought that the Catholic Church was a good enemy to have.

The thinking from the right was something akin to "uh-oh."

Obama publicly pretended to be considering widening the religious exemption, offering a heavy dollop of conciliatory verbiage. In November, President Obama asked Abp. Dolan to meet. James Taranto recently reported on this meeting:

Mr. Obama knew that the mandate would pose difficulties for the Catholic Church, so he invited Archbishop Dolan to the Oval Office last November, shortly before the bishops' General Assembly in Baltimore. At the end of their 45-minute discussion, the archbishop summed up what he understood as the president's message:  "I said, 'I've heard you say, first of all, that you have immense regard for the work of the Catholic Church in the United States in health care, education and charity. . . . I have heard you say that you are not going to let the administration do anything to impede that work and . . . that you take the protection of the rights of conscience with the utmost seriousness. . . . Does that accurately sum up our conversation?' [Mr. Obama] said, 'You bet it does.'"

The archbishop asked for permission to relay the message to the other bishops. "You don't have my permission, you've got my request," the president replied.  "So you can imagine the chagrin," Archbishop Dolan continues, "when he called me at the end of January to say that the mandates remain in place and that there would be no substantive change, and that the only thing that he could offer me was that we would have until August. . . . I said, 'Mr. President, I appreciate the call. Are you saying now that we have until August to introduce to you continual concerns that might trigger a substantive mitigation in these mandates?' He said, 'No, the mandates remain. We're more or less giving you this time to find out how you're going to be able to comply.' I said, 'Well, sir, we don't need the [extra time]. I can tell you now we're unable to comply.'"

This is the part of the story where President "I won" Obama was supposed to do a touchdown dance to the cheers of liberals everywhere.

President Obama had the enemy he wanted or at least one he didn't fear at all.

But something unexpected happened. In recent months under the guidance of Archbishop Dolan, priests and bishops spoke out publicly and forcefully in a way that few can remember having been done previously.
So effective was the pushback that Obama blinked or maybe he just pretended to blink. He sought new phrases and new clarifications. He sought "an accounting gimmick" to make his policy seem more acceptable.

Recent weeks must have proved even odder for the Obama administration in that they received everything they wanted from the media. A story spoon fed to them had Rush Limbaugh calling Georgetown Law student a name that we're not going to mention here and the media treated it like the story of the century. Nancy Pelosi allowed the young woman a one-woman show hearing and President Obama himself called her. Talking heads were crowding into camera frame to declare this the greatest week ... evah for President Obama.

But a funny thing happened. Nothing. Obama's approval ratings didn't go up. Cardinal Dolan and the Catholic Church didn't change their mind. The fight continued.

The Obama administration wasn't ready for this kind of political enemy because it wasn't an enemy who played politics. You see, the "compromise" was a perfect offering for a would-be politician looking for an excuse to sidestep a continued direct confrontation with the most powerful man in the world. Obama had gotten into these fights before and when he offered a way out, his opponents took it. And they were grateful for it. But Cardinal-designate Dolan didn't step to the side.

When Cardinal Dolan said "We will not comply" he wasn't sloganeering. He was saying what he meant. He didn't mean that he'll put up a bit of fight to make it look good. He meant we will not comply.

This wasn't something the Obama administration knew how to handle.

Obama was the "I won" President and Cardinal Dolan was supposed to be a middling figure of a reportedly disappearing organization. This wasn't supposed to be the fight that would define the Obama presidency.

This wasn't supposed to be a fight that Obama could lose. It wasn't supposed to happen this way. And the Church is just getting started.