On February 17, some 35,000 people showed up for a march outside the White House to protest construction of the Keystone XL oil pipeline. The environmental lobby is going all out to stop the pipeline, which will transport oil from Alberta, Canada, to refineries near Houston. In its ongoing offensive against the project, the Sierra Club has endorsed civil disobedience for the first time in its 120-year existence. A Sierra Club protest outside the White House on February 13 culminated in the arrests of actress Daryl Hannah, former NAACP chairman Julian Bond, and Robert F. Kennedy Jr.

The surprising thing is not an environmental lobby’s effort to stop a pipeline, but how successful it has been, given that building Keystone XL is a top priority for another powerful Obama constituency—unions. The $5.3 billion project is expected to create 20,000 jobs in the United States, with a great many of them going to union members. After initially approving the project in 2011, the administration has found various ways to delay breaking ground.

Unions were willing to cut Obama some slack on delaying the pipeline, understanding that the president didn’t want to alienate environmentalists until his reelection was secure. Last August, after the White House had dithered on approving the project for over a year, AFL-CIO head Richard Trumka told The Weekly Standard he was unconcerned. “I think we can get it done in the second term,” he said. In the months leading up to the election, Trumka asserted his belief the pipeline would be built once Obama was reelected so often that it bordered on braggadocio.

On January 19, the day before Obama was sworn in for a second term, the president rejected yet another permit to build the Keystone XL pipeline. This postpones a decision on the project to “the beginning of summer at the earliest,” an anonymous official told Reuters. When and if the pipeline will be built remains anybody’s guess. It’s true that not all unions are enthusiastic about the construction of the pipeline. But the AFL-CIO isn’t simply another union—it’s the nation’s largest confederation of unions, spending hundreds of millions of dollars to elect Barack Obama and Democratic allies over the last three election cycles.

The really bad news for unions is that the Keystone XL episode is emblematic of a much larger failure of organized labor’s political strategy. To be fair, calling it a strategy may be generous. After the resounding Republican victory in 2004, unions simply resolved to spend as much money as they could to elect as many Democrats as possible.

Since 2008, unions have doled out more than $1 billion in campaign cash, including over $400 million in 2012. And that’s just what the unions own up to spending. Thanks to transparency requirements put in place by the Bush administration’s Department of Labor, the Wall Street Journal was able to estimate last year that labor unions spent $4.4 billion on political activities between 2005 and 2011. Union political spending now exceeds all other direct political donations, though this essential fact is ignored in the incessant media harrumphing over super-PACs, special interests, and other campaign finance issues. The GOP wave in 2010 notwithstanding, union spending has been pretty successful at securing Democratic victories. Policy victories, though, have been harder to come by.

Aside from the delay of the Keystone XL pipeline, three other union developments since Obama’s reelection bear mentioning. In December, Michigan, home of the United Auto Workers and long considered an impregnable union stronghold, outlawed union membership as a condition of employment and became a right-to-work state. Even coming on the heels of recent failures to stop public employee union reform in Wisconsin and the success of right-to-work legislation in Indiana, no one had imagined this happening in Michigan. Public employee union reform was turned back in Ohio—but only after unions spent $40 million on a scorched-earth campaign that included ads warning modest changes to collective bargaining laws would make it “harder for nurses to give the patients the quality care that they need” and “take us back to the days of Jim Crow.” But if compulsory unionism can’t be defended in Michigan, it’s probably endangered everywhere. Already there’s a movement gaining steam to put a right-to-work measure on the Ohio ballot this year. The days of labor laws being rigged in favor of unions are numbered.

The second development worth noting is that a federal appeals court ruled on January 25 that three of Obama’s recess appointments to the National Labor Relations Board are invalid. While the White House has been quick to give unions short-term political payoffs such as billions in stimulus construction contracts, Obama’s pro-labor appointments to the NLRB were one of the few tangible things the administration had done to deliver long-term structural benefits to unions. Those appointments have now backfired spectacularly.

After helping elect Obama in 2008, unions demanded their own personal fox be appointed to guard the NLRB’s henhouse. Craig Becker, a former attorney for the AFL-CIO and the Service Employees International Union, who had authored a law review article arguing “employers should have no right to be heard” in a wide swath of labor disputes, was to be appointed to the federal body that’s supposed to arbitrate disputes between labor and management. Becker’s appointment was so controversial that his nomination to the NLRB failed in the Senate on a bipartisan vote.

Regardless, Obama installed Becker with a recess appointment. True to form, Becker was behind a flurry of controversial pro-union NLRB decisions, heard several cases involving his former employers, and even ruled on an NLRB decision despite having filed a brief in the case as a lawyer a few years before. This all led up to his involvement in the Boeing fiasco, in which the NLRB told the aviation giant that it couldn’t open a new plant in right-to-work South Carolina while it was embroiled in a labor dispute in Seattle. In effect, the supposedly impartial NLRB put pressure on a private company to resolve a labor dispute in favor of the union.

Becker’s recess appointment expired, and Obama was facing additional vacancies on the board. With the business community justifiably fearing that Obama would continue to politicize the NLRB, Senate Republicans threatened to block Obama from making recess appointments, denying the board a quorum and hobbling it. There is precedent for blocking recess appointments—when President Bush started making recess appointments after the Democratic-controlled Senate did nothing to approve a backlog of 190 appointees, Senate majority leader Harry Reid retaliated with 30-second-long “pro-forma” sessions on days off so the Senate would technically not be in recess. Bush made no more recess appointments.

Facing threats to have his nominees blocked, Obama made three recess appointments to the NLRB—disregarding whether the Senate was in recess. The federal court’s rebuke was sharp. Allowing such appointments, it held,

would demolish the checks and balances inherent in the advice-and-consent requirement, giving the President free rein to appoint his desired nominees at any time he pleases, whether that time be a weekend, lunch, or even when the Senate is in session and he is merely displeased with its inaction. This cannot be the law.

The court’s ruling also invalidates all of the decisions the NLRB has made in the past year, including hugely significant decisions in which the NLRB overturned a 50-year precedent and ruled that employers have to continue collecting union dues after a collective bargaining agreement has expired. This gives employers significantly less leverage in labor negotiations and would constitute a major union victory had it been allowed to stand.

The NLRB is moving forward in defiance of the ruling, but questions surrounding its validity and recent history of activism abound. The board risks significant political blowback if it courts more controversy. Republicans have been kicking around a bill for some time that would abolish the NLRB, and there’s a strong case to be made for doing just that. The number of labor disputes is no longer sufficient to justify resolving them with a politicized administrative body rather than in the courts. When the NLRB was created in 1935, one in five American workers was unionized. Union numbers, at least in the private sector, have dwindled considerably since then.

As it happens, the latest membership numbers are the third postelection development that augurs poorly for unions. Though union membership has been steadily declining, it dropped steeply last year. Union membership, now 11.3 percent of the workforce, is at its lowest level since 1916, according to Labor Department statistics released in January. Just 6.6 percent of the private sector workforce is unionized. If electing Democrats was supposed to stop the bleeding, it turns out to have been a mere bandage at a time when a tourniquet was needed.

Taken together, these three developments paint a picture of how the political efforts of a professional class of union bosses have failed workers. They spent vast sums on federal electioneering, instead of shoring up local unions and exerting influence at the state level, where they were most vulnerable. And despite Democrats’ owing their victories to billions in union dues, union bosses failed to extract meaningful structural changes when Democrats controlled Congress or when the president needed support for his reelection bid. In the end, unions gave Barack Obama everything. Now all they’ve got to show for it is a second-term president who seems to feel he owes them nothing.

Mark Hemingway is a senior writer at The Weekly Standard.

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