FORTUNE — Remember how the 2008 presidential election turned on the debate over education reform? And then how Democrats and Republicans finally came together on a national energy policy that called for massive investments in wind power? And who could forget just a few months ago when policymakers resolved the fiscal cliff crisis by striking a sweeping deficit reduction agreement that overhauled entitlement programs and the tax code?
There may be alternate realities in which CEOs solved big, entrenched policy problems by throwing wads of their own money at them. Just not this one. So the precedent for Mark Zuckerberg as he launches his attempt at bending Washington leaders to his will is less than encouraging.
The 28-year-old billionaire is rallying fellow Silicon Valley chief executives to pitch in for a new advocacy group that will lean on Congress to pass comprehensive immigration reform and then move on to other issues. He’s already assembling a team of consultants steeped in both lobbying inside Washington and waging political campaigns out in the states, suggesting he’s looking to borrow the playbook from Mike Bloomberg’s ongoing gun-control quest and will be meting out electoral reinforcement. His reported initial fundraising goal of $50 million indicates his seriousness of purpose — no Potemkin “earned media” campaign here.
But the recent history of billionaires trying to break through the Beltway logjam shows those efforts achieved little besides separating their sponsors from some of their bankrolls. Take original tech capo Bill Gates. Back in 2007, he teamed with fellow billionaire entrepreneur Eli Broad to try to make school improvements the defining issue in the presidential campaign. They jointly pledged $60 million to the cause, set up a fully staffed office in downtown Washington, and hired teams to get the word out in the early primary states of Iowa, New Hampshire, Nevada, and South Carolina. Operating under the banner “ED in ‘08” the group developed a policy tool kit, staged events around debates, ran ads, and recruited grassroots support. It was for naught. The election turned on the economic crisis, and, to a much lesser degree, the war in Iraq. Education didn’t rank, and whether the group’s push ever prompted so much as a twitch in the national debate is arguable.
The story repeats itself. During the same campaign season, billionaire Texas oilman T. Boone Pickens kicked off his quixotic drive to wean the United States off foreign oil by transitioning the American auto fleet to natural gas and replacing it as an electricity source with wind power. He committed $58 million of his fortune — and his inexhaustible charisma — to promoting the effort. The money funded an ad blitz and helped him recruit an online army of converts. More than $400,000 in lobbying help from an array of firms helped him make inroads on Capitol Hill. But as the price of oil plummeted, lawmakers shrugged off his pitch. Pickens has since shelved his plans for building a huge Texas wind farm.
More recently, a broader contingent of CEOs, many from Wall Street, ponied up $43 million from their own pockets to force a resolution to the fiscal standoff that’s dominated our politics for the last two years. The initial aim of the Fix the Debt campaign was to leverage the year-end pileup of austerity shocks into a long-term agreement to shave trillions from federal spending. The CEOs made a lot of noise, even inspiring CNBC to hop aboard with wall-to-wall coverage the network branded “Rise Above.” Starbucks (SBUX) CEO Howard Schultz pitched in by drafting DC-area baristas to scrawl “Come Together” on cups. Alas, as with so many other deadlines, the White House and Congressional Republicans averted the fiscal cliff with a punt that achieved a fraction of the savings the CEOs sought.
It’s too early to judge whether Bloomberg’s drive to tighten gun restrictions in the wake of the Newtown massacre will prove more successful. The billionaire is putting bite behind his advocacy by using a super PAC — the new must-have for the politically inclined rich — to try to answer the NRA’s clout. Last fall, he spent $3 million to oust eight-term Rep. Joe Baca, a pro-gun California Democrat. He spent another $2 million last month in a special election for a Chicago-area Congressional seat, helping secure victory for a gun-control advocate over the NRA-endorsed candidate. But momentum for a comprehensive new gun law appears to be waning on Capitol Hill.
Zuckerberg’s project, meanwhile, is still in its formative stages. How it fits itself into a scene already crowded with deep-pocketed players remains to be seen. There’s already an organization in Washington representing CEOs — the Business Roundtable. Its head, former Michigan governor John Engler, who served on the steering committee for Gates’ 2008 campaign, welcomed the Facebook (FB) chief to the table with a cautionary note: “Whether or not a group like this will stand out in what is a fairly cluttered playing field will depend on the uniqueness of their ideas and how they advance them,” he said.
Indeed, there’s already an organization representing just CEOs from Silicon Valley. TechNet, founded in 1997 by Kleiner Perkins partner John Doerr and Cisco (CSCO) CEO John Chambers, lobbied successfully against trial lawyers for a law limiting shareholder lawsuits. Its profile has shrunk considerably since, and it now belongs to a desultory alphabet soup of tech-focused lobby groups. Dan Schnur, a political director for TechNet when it launched and now the director of the Jesse M. Unruh Institute of Politics at the University of Southern California, says Zuckerberg’s involvement alone will mean “triple the media coverage and quadruple the attention on Capitol Hill.” But he predicts the group’s success will turn on the CEO’s commitment to it. “The most important lesson from those previous efforts is that it’s not simply enough to have a checkbook and good intentions. You have to have ongoing top-level involvement.”