Even in an election year in which Democrats in swing states are losing re-election by wide margins, Colorado U.S. Senator Michael Bennet would seem to be a shoo-in for a full term. Since his appointment last year by Gov. Bill Ritter to replace now-U.S. Secretary of the Interior Ken Salazar, the freshmen has built something of a reputation as a bland moderate thanks to his professed opposition to parts of the Employee Free Choice Act (Card Check) and President Barack Obama’s plans for a third round of stimulus spending.

A former Denver schools superintendent, Bennet is particular favorite of the centrist Democrats who now hold sway over President Barack Obama’s education policy agenda thanks to his successful battle with the National Education Association to subject Denver teachers to private sector-style performance management. Although the rest of Bennet’s record is a little light on bold initiatives (and despite his unwillingness to say if he supports or opposes charter schools), he has still won plaudits from advocates such as Whitney Tilson, a teacher-turned-hedge fund manager who is one of the movement’s most-prominent financiers. Declares Tilson: “I’d strongly support him even if he weren’t an innovative leader in education reform — which he is.”

But these days, Bennet is having as much trouble keeping office as Senate Majority Leader Harry Reid. After surviving a rough primary battle against a former state house speaker, Bennet trails another veteran politician, Weld County District Attorney Ken Buck by two points (according to Rasmussen Reports). Bennet has gotten so desperate that he is now depending on help from the NEA, which is spending $1.4 million of its massive war chest on his behalf.

Meanwhile conservatives and progressives alike have taken Bennet to task for studiously avoiding positions on any issue. The senator’s latest clarification of his stance on Card Check garnered a Bronx cheer from Huffington Post contributor (and longtime Bennet critic) David Sirota, who notes that Bennet’s been “trying to dance away from answering any questions on the issue.” The headline on Denver Post writer David Harsanyi’s column about the senator summed things up more succinctly: “Where’s Michael Bennet on Health Care? Anywhere He Needs to Be.”

As with fellow moderate Evan Bayh (whose milquetoast reputation has cost him a third term in the Senate), Bennet’s woes are a reminder that wishy-washy politicians will pay dearly for playing both sides of the fence far too often. This is especially true for someone like Bennet, who, unlike Bayh, has no previous experience running for office and thus, little mastery of the art of dancing the political Texas Two-Step. Save for rare exceptions such as former federal budget director-turned-Indiana governor Mitch Daniels and legendary U.S. Senator Daniel Patrick Moynihan (a former diplomat and policy wonk), most mandarins haven’t successfully transitioned from bureaucrat gamesmanship into political office.

School reformers, who are backing Bennet so fervently, also have lessons to learn. They have won over reform-minded politicians and such filmmakers as An Inconvenient Truth director Davis Guggenheim (whose documentary on America’s woeful public schools, Waiting for Superman, is far more entertaining). But they haven’t mastered the brutal art of election politics, in which hard-hitting campaign ads and mobilizing bodies on the ground matter more than arcane policy discussions. As a result, they are often bested by teachers unions, who have what politicians care for most: Vast campaign war chests and armies of teachers ready to work the polls. School reformers won’t succeed in politics until they learn how to play the game — including developing and picking stronger candidates.

THE SON OF A DIPLOMAT WHO RAN the U.S. Agency for International Development under Jimmy Carter (and grandson of a former adviser to FDR), Bennet parlayed his Democratic Party ties into stints with Ohio governor Richard Celeste and the Clinton Administration before spending six years in the private sector helping billionaire Philip Anschutz put together a string of mergers that formed movie theater giant Regal Cinemas.

By 2003, Bennet found himself another powerful patron in Denver Mayor John Hickenlooper, who first made him his chief of staff, then helped him become superintendent of Denver’s woeful public school system two years later. Save for some small moves and for forcing the NEA’s Denver local to go along with ProComp, one of the first efforts to replace traditional degree- and seniority-based pay scales with one based on improving student achievement, Bennet’s tenure was marked by studious poses and what one local education writer charitably called a “visionary, if vague, reform plan.”

Despite the sparse credentials, Bennet was briefly considered by Obama for Secretary of Education in 2008 before he picked the more successful Arne Duncan. A month later, Bennet beat out more experienced politicians (including former boss Hickenlooper) for an even bigger job: Appointment to fill Salazar’s remaining term in the U.S. Senate. But his dearth of experience, lack of support among party activists, awkward efforts at fitting in with fellow Coloradans (including donning western boots and poses in the outdoors), and penchant for mealy-mouthed positioning put him in the cross-hairs.

Early on, Bennet was pilloried by progressives and conservatives alike for his waffling on the public option element of Obama’s healthcare reform plan (he eventually signed a letter asking Reid to include it in Senate legislation). Bennet angered progressives even more when he voted against an Obama plan that would have allowed bankruptcy judges to force banks to rewrite the terms of defaulted mortgages and stop foreclosures.

By March, Bennet found himself staving off a primary battle against Andrew Romanoff, a former speaker of Colorado’s lower house, who managed to obscure his own centrist (and pro-death penalty) leanings and transform himself into a champion for the hard-left elements of the Democratic Party. Despite efforts by Bennet’s patrons and the Obama Administration to snuff out the bid with threats and offers of patronage jobs, Romanoff managed to best Bennet in a Democratic Party straw poll by a two-to-one margin.

Thanks to the efforts of his longtime patrons (and Romanoff’s lack of cash), Bennet eventually beat Romanoff back. But now he must tangle with Buck, who won the GOP senatorial nod (and beat the state’s lieutenant governor) by rallying support from Tea Party activists. Bennet still isn’t doing such a hot job on the campaign trail. An appearance last week with New York Jets linebacker Jason Taylor — on the day the team was playing against the hometown Denver Broncos — didn’t exactly do Bennet any favors. A confrontation with one aging voter, who demanded to know why the healthcare reform plan didn’t require coverage of the impotence drug Viagra, was even less impressive. Wrote Slate columnist David Weigel: “[Bennet’s] answer sounded like his answer to almost everything: Isn’t it a shame that people can’t get along?”

Meanwhile Bennet has said little, if anything, about school reform. When it comes to education, Bennet has done little more than run ads attacking Buck for allegedly wanting the abolishment of the U.S. Department of Education. This isn’t exactly surprising. School reform outfits such as Education Reform Now have ponied up some donations to Bennet’s campaign and even bought a few small ads; the prominent group Democrats for Education Reform put in $11,000 into Bennet’s campaign. But their sums are paltry compared to that being spent by the NEA on the senator’s behalf for the last few weeks of the election season alone. Expect the teachers union to get a little more of Bennet’s attention next year (if he manages to overcome Buck’s lead).

Whether Bennet wins or not, his campaign offers some object lessons for wishy-washy moderates and school reformers alike.