On Friday morning, John Boehner announced he will be resigning from his position as speaker of the House, and from his congressional seat, in October.  Many conservatives greeted this news with unbridled adulation.  Breaking the news to his audience at the Values Voter Summit on Friday morning, Marco Rubio sent the crowd into a frenzy, despite adding that he’s not “here to bash.”

How did it get to this point for Boehner?  Where did it go wrong for the person who Vox’s Dylan Matthews claimed “did more to reduce the size of the federal government than any other politician in recent memory”?

We can boil down conservative dissatisfaction with the speaker to two main criticisms: (1) he did not resist President Obama’s liberal agenda as fully as he could have, and (2) he did not articulate a conservative alternative to Obama winsomely enough.

In his nearly five full years as speaker, Boehner did much to slash spending.  But he also did much to avoid putting the kind of pressure on Obama that conservatives clamored for.  Recall that Boehner was elevated to speaker during the 2010 midterm elections, widely regarded as the high political moment of Tea Party sentiment.  The resounding message from conservative voters was that they wanted significant pushback against the president’s agenda – not just in terms of winning legislative victories, but in terms of vocalizing their deep antipathy toward the president’s attempts to "fundamentally transform the United States of America."

Certainly Boehner’s speakership generated outcomes that conservatives far preferred to those achieved during the Obama-Pelosi partnership.  But Boehner was too much of a deal-maker, too much of a backroom tactician, to satisfy the conservative political yearnings of the moment.  Obama’s presidency portended sweeping liberal changes, announced in lofty, soaring language.  Combating this program with backroom compromises was never going to be enough.  The people demanded visible resistance; they got covert counterproposals instead.

But it would be a mistake to leave it at that, for Boehner’s failure went beyond mere appearances.  There is a substantive point here about how political aggressiveness can become electorally inspirational.  The last five years have provided example after example of conservative disaffection with Washington’s Republican compromisers.  Had Boehner adopted a stronger policy of denunciation, an absolute refusal to compromise, he might have engineered conservative victories – not in the legislative sphere, which would have been repelled by Obama, or, until recently, defeated by Harry Reid, but in the political sphere more broadly, in the form of American approval.

Jonathan Chait writes: “Boehner and the party leadership have resisted [shutting down the government] not because they agree with funding Planned Parenthood, but because this tactic has no chance of success.”  But could it be that there are ways of measuring success other than simply registering whether a bill is passed or not?  Could it be that the American people, as a result of being exposed to an endless loop of the Planned Parenthood videos, have come to see Obama’s refusal to strip funding for the abortion provider as the cause of the shutdown?  Why take the view that Republicans will always endure the blame for a shutdown?  This was never even debated.  It was accepted that Obama would never go for it, so the Republican leadership – not just Boehner, but McConnell, too – laid off.  But this reveals a troubling lack of political imagination, which brings us to the second criticism.

Boehner, unlike Newt Gingrich in the mid-1990s, has lacked anything resembling a political vision able to win over the American public.  I have spoken of Obama’s ability to present his policies in shiny packaging.  There was nothing of comparable political allure from Boehner, nothing approximating a captivating ideological profile that could run counter to the president’s project to reshape America along even more liberal lines.  In short, Boehner lacked the political imagination to succeed as the president’s most visible legislative opponent.

It’s striking that Boehner, who played an important role in Gingrich’s "Contract with America" in 1994, would fail to understand how important it is to captivate the public.  Gingrich’s Contract, issued under circumstances similar to the opportunities Boehner himself enjoyed in 2011, was a sharp, forceful, and dynamic alternative to Bill Clinton’s political agenda.  By contrast, 2010’s "Pledge to America" came up well short of offering a lasting, winsome conservative alternative to Obama.  It was too defensive, too reactionary, too negative.  (Interestingly, it was penned by Kevin McCarthy, the current odds-on favorite to assume the speakership once Boehner resigns next month.)

John Feehery notes that “Mr. Boehner knew how to cut deals and how to make good laws. What he didn’t know how to do was reconcile an angry conservative movement with an implacable liberal president. … But no political leader could have brought those two forces together.”  But why should it be the Republican leader of the House’s job to “bring those two forces together”?  That assumes a liberal understanding of governance; for conservatives, obstructing bad policies is arguably more important than passing legislation.  If conservatives are for smaller government, then it follows they won’t be pursuing legislative changes with the same expansive zeal that possesses their liberal counterparts.  But crucial to rightly understanding American electoral politics is that this negative, or destructive, approach needs to be articulated properly and winsomely if the conservative agenda is going to have success.  The act of demolition doesn’t naturally inspire; the people have to be shown how an agenda that pushes back against government encroachment is the most life-affirming program that there is.

This is where political imagination comes in.  And Boehner, for all his accomplishments, did not have any.