“My goal is to see that all Americans are treated equally regardless of sexuality,” he told me when we met. Tall and lean, Gill is a vigorous fifty-three years old, a sci-fi buff and an avid snowboarder (he runs a social networking site for gay snowboarders, called Outboard). He was dressed in the manner of a successful Denver businessman—casual, but not overly so, in jeans, a sports shirt, and Italian leather shoes. In our conversations, he gave the impression of someone who feels he has been picked on and now, having acquired the means, fully intends to do something about it.
Gill led me through his evolution as a donor. For years he gave generously to gay organizations and dutifully supported gay-friendly candidates. His guiding ambition was helping to teach other donors and nonprofits how to operate more efficiently, and he had organized a series of major-donor conferences toward that end. But several years ago, a growing number of his peers began to sense that they were playing in the wrong arena. “A lot of [gay donors] are driven, cycle to cycle, by the notion that there’s going to be an epiphany—that one day they’ll wake up and accept us,” he said. “But this group had spent millions of dollars on philanthropy, and yet woken up the morning after the election to see gay-marriage bans enacted all across the country.”
Gill decided to find out how he could become more effective and enlisted as his political counselor an acerbic lawyer and former tobacco lobbyist named Ted Trimpa, who is Colorado’s answer to Karl Rove. Trimpa believes that the gay-rights community directs too much of its money to thoroughly admirable national candidates who don’t need it, while neglecting less compelling races that would have a far greater impact on gay rights—a tendency he calls “glamour giving.” Trimpa cited the example of Barack Obama: an attractive candidate, solid on gay rights, and viscerally exciting to donors. It feels good to write him a check. An analysis of Obama’s 2004 Senate race, which he won by nearly fifty points, had determined that gays contributed more than $500,000. “The temptation is always to swoon for the popular candidate,” Trimpa told me, “but a fraction of that money, directed at the right state and local races, could have flipped a few chambers. ‘Just because he’s cute’ isn’t a strategy.”
Together, Gill and Trimpa decided to eschew national races in favor of state and local ones, which could be influenced in large batches and for much less money. Most antigay measures, they discovered, originate in state legislatures. Operating at that level gave them a chance to “punish the wicked,” as Gill puts it—to snuff out rising politicians who were building their careers on antigay policies, before they could achieve national influence. Their chief cautionary example of such a villain is Senator Rick Santorum of Pennsylvania, who once compared homosexuality to “man on dog” sex (and was finally defeated last year, at a cost of more than $20 million). Santorum got his start working in the state legislature. As Gill and Trimpa looked at their evolving plan, it seemed realistic. “The strategic piece of the puzzle we’d been missing—consistent across almost every legislature we examined—is that it’s often just a handful of people, two or three, who introduce the most outrageous legislation and force the rest of their colleagues to vote on it,” Gill explained. “If you could reach these few people or neutralize them by flipping the chamber to leaders who would block bad legislation, you’d have a dramatic effect.”
Gill’s idea was to identify vulnerable candidates like Danny Carroll and move quickly to eliminate them without the burden of first having to win the consent of some risk-averse large organization or board of directors. Another element of this strategy is stealth. Revealing targets only after an election makes it impossible for them to fight back and sends a message to other politicians that attacking gays could put them in the crosshairs. Independence also allowed Gill to pursue an element of his philosophy that chafes many national gay organizations: the belief that enduring acceptance can be won only with Republican support. “If you want a majority, you have to change people’s minds,” he said, noting that in Colorado, Republicans outnumber Democrats. “Just because you’re conservative doesn’t mean you’re antigay.”
With that in mind, he assembled a bipartisan team of political operatives and tested his theory in 2004, quietly targeting three antigay Colorado incumbents; two of them went down. Through the combined efforts of a host of progressive interest groups, including many supported by Gill, Democrats captured both chambers of the legislature for the first time in forty years. Gill’s decision to back Democrats in Colorado was the only choice that would produce the gay-tolerant leadership he’s pursuing. But ten years from now, he told me, he hopes he’ll be able to give evenly to Republicans and Democrats.
Convinced his approach was sound, Gill decided to go big. When I visited his headquarters last fall, liberals were working alongside conservatives on a list compiled by his top consultants—one a national Democratic consultant, the other a former Karl Rove protégé—of seventy races in which a key antigay candidate was vulnerable or the outcome of a race was likely to affect control of the legislature. The list included state legislators, governors, and judges, not just Republicans but Democrats as well—like Philip Travis, the Democratic legislator leading the push to overturn gay marriage in Massachusetts.
From the standpoint of an entrepreneur, Gill saw opportunity and believed he could amplify his return on investment. Last spring, he sponsored another conference for wealthy gay donors, only this one designed to steer money to the right political races instead of the right nonprofits. His pitch was simple: Instead of waiting for a political savior to fix everything, consider donating to these races, where you’ll have more effect at a fraction of the cost. As Trimpa later characterized the rationale for such an approach: “We live in a post–Will & Grace society. Americans believe and understand that gay people are everywhere, and most view them in a mainstream context. But this is a recent development, and the political world has not yet caught up—it’s lagging behind. The day will come when all of this is aligned, but we’re not there yet.”
In the 2006 elections, on a level where a few thousand dollars can decide a close race, Gill’s universe of donors injected more than $3 million, providing in some cases more than 20 percent of a candidate’s or organization’s budget. On Election Day, fifty of the seventy targeted candidates were defeated, Danny Carroll among them; and out of the thirteen states where Gill and his allies invested, four—Iowa, Michigan, Pennsylvania, and Washington—saw control of at least one legislative chamber switch to the Democratic Party. (In Massachusetts, Travis decided to retire rather than seek reelection.) The national climate, which was strongly anti-Republican, helped bring about this transformation. But Gill’s stealth campaign was both effective and precedent-setting. For the first time, in a broad and organized way, gays had taken the initiative in a sweeping multistate strategy and had mostly prevailed.