Mitch McConnell’s outside man, Steven Law, plays the long game

Democrats were gaining traction on a legislative reform and Mitch McConnell was looking for a way to quash it.

It’s a familiar Washington storyline now, but at this particular time, almost 27 years ago, the prospects for a bill that would have limited campaign spending and provided some public funding for congressional candidates were real.

Steven Law, then McConnell’s chief of staff, huddled with a parliamentary expert in their Senate office and found good news: Because of differences between the campaign finance limits the House and Senate wanted to impose, multiple motions were required to move the bill to a conference.

McConnell, then only in his second term, could deploy the filibuster to delay the process and eventually exhaust the opposition. He did and it worked. The moment was a formative one for McConnell, who drew respect from his GOP colleagues and considerable media attention for crowing to Democrats that he was proud to kill “this turkey of a bill.”

“We just ground them down,” Law recalled. “There’s a point they just realized this is never going to stop. And they folded their tent.”

Sitting inside a downtown D.C. cafe during one of several conversations, Law offered up a straightforward lesson that’s prescient decades later in the current battle over electoral reforms: “Writing the rules of the games in campaigns and elections ... can shift the playing field.”

Perhaps more than any single operative in Republican politics over the past decade, Law has altered the modern political playing field by collecting enormous sums of money to deploy against Democratic candidates and prop up Republicans. As the president and chief executive officer of American Crossroads and the Senate Leadership Fund, he remains at the helm of the largest and most influential Republican super PACs of the era that are working to make McConnell majority leader again in 2023.

And it all began with the Kentucky senator 34 years ago, establishing Law as the longest-serving and most influential confidante in McConnell’s orbit.

“It would be difficult to measure the enormous impact Steven Law has had on decades of Republican politics,” McConnell said in a statement to McClatchy. “I’ve been fortunate to draw on his razor-sharp political instincts and brilliant strategic thinking, as have successive Senate Republican majorities over the years.”

Many Republicans acknowledge they likely wouldn’t even be in a position to retake the Senate without the hundreds of millions of dollars Law has amassed from Republican donors, who are almost all extremely wealthy and largely anonymous.

Critics of the unlimited, unregulated money cite Law as the purveyor of the practice that is now commonly embraced by both parties and seen as almost an afterthought.

“There are very few people like Steven Law when it comes to the post-Citizens United era,” said Robert Maguire, research director for Citizens for Responsibility and Ethics in Washington, who has written critically about his groups lack of transparency. “They’re catering to these donors, giving them weekend retreats with lawmakers...We’re talking about access that regular Americans don’t get.”

In 2020 alone, with the historic 2021 Georgia runoffs included, the Senate Leadership Fund spent more than $600 million to battle Democrats to an evenly split upper chamber. Law doesn’t expect to top that gargantuan number in 2022, but it’s safe to say that SLF will be leaned on to make up the difference in places like Georgia and Arizona, where Democratic incumbents are stockpiling early financial advantages. One Nation, a nonprofit under the Crossroads/SLF organizational umbrella, has already unleashed a couple million dollars against Democratic incumbents this year.

“It’s McConnell’s faith in Steven, the donors faith in Steven,” said Carl Forti, who serves as Crossroads’ political director.

Staffers and aides regularly come and go from Capitol Hill and party committees -- usually to cash out with leaner hours at a lucrative trade organization, white shoe lobbying firm or private sector company. What makes Law different is his longevity and affability. It’s hard to stick around for such a long time conducting political warfare and not accumulate a handful of enemies, especially within one’s own party. But even operatives who convey they’ve disagreed with Law at a given moment over the years, acknowledge they just plain like the guy.

Kevin McLaughlin, a former executive director of the NRSC said he first met Law during a bipartisan AIPAC trip to Israel in 2015, where Law ended up dancing on a bar in Tel-Aviv on one night of memorable revelry.

Former President Barack Obama once joked that he’d rather not have a drink with McConnell. But apparently some Democrats feel differently about Law, who favors Negronis.

“All the Democrats wanted to hate him. He’s the dark money guy! And they loved him,” McLaughlin recalled. “You can’t hate him.”

Craig Varoga, a veteran strategist who has run Democratic super PACs, describes Law as a “smart, super pleasant guy,” an “able competitor who doesn’t miss a trick” and a professional who predates all the insanity” of Trumpism.

“He’s probably having nightmares about the QAnon types, MAGA super nuts and others who are running in Republican Senate primaries next year,” Varoga said.

At 61, Law is still in the center of the field and serving McConnell -- just from the outside.

And with every Senate election a potential majority maker next year -- and the second half of President Joe Biden’s agenda riding on the outcome -- 2022 might just become his most challenging game yet.

“The path to the majority in the House is clearer, and therefore appears more likely,” Law said. “On the Senate side, it’s just less clear.”

‘We might lose’

Law first met McConnell in February 1987. He was making close to nothing as a young aide to New York Sen. Al D’Amato and seeking an exit ramp. The freshman McConnell was looking for a lawyer and the Ivy League educated Law charmed him in their first meeting, yielding “not a full-fledged grin, but a gentle smile” from the usually stoic senator.

Hired the next month, Law was initially tasked with the portfolio of tort reform and judicial nominations. But once Democrats began to gain momentum on campaign finance reform, McConnell asked Law to prioritize a plan to stop it. McConnell was concerned there wasn’t enough robust opposition to it within the Republican caucus and he worried President George H.W. Bush might not veto it.

“His view was, ‘Kill it here,’” Law said.

It morphed into a years-long battle but they were successful in beating reforms back during both the Bush and Clinton administrations.

McConnell then tapped Law to run his 1990 re-election campaign, when it was still a challenge to be elected statewide as a Republican in Kentucky. The senator was endangered by a “throw the bums out” midterm feeling that brewed from Bush breaking his “Read my lips” pledge to not raise taxes.

McConnell’s numbers were dropping and the Wednesday before the election, their pollster delivered a gut-punch to Law. McConnell was behind, on track to lose. Law described a disposition he hadn’t seen before: McConnell was “rattled.” So the senator made what was a controversial call among his team. He wanted to cut a positive TV ad to cut through the ugliness permeating the campaign season.

Almost all of McConnell’s aides were dead-set against it, including Roger Ailes, but McConnell had made up his mind and ordered up the spot. He won by 4 points in a year Democrats picked up seats in both the House and Senate.

“He was really right. He turned it around. He just gritted it out,” Law said. “There were several days where he and I were both thinking we might lose, and he just soldiered on.”

Sports car or Super PAC?

McConnell appreciated Law’s effort as well, elevating him to his chief of staff in Washington and then transferring him to steer the National Republican Senatorial Committee in 1998 when McConnell became chairman.

Law would even go on to work for McConnell’s wife, as chief of staff and deputy secretary to Elaine Chao when she was tapped to run the Labor Department in President George W. Bush’s administration.

Having served in nearly every possible role in McConnell’s world, Law decamped to the private sector, landing the coveted and lucrative position of general counsel at the U.S. Chamber of Commerce. A year later, Barack Obama won the White House, Democrats added eight Senate seats and the Republican Party looked like they were stuck in the wilderness.

In the fall of 2009, GOP operatives Karl Rove and Ed Gillespie met to plot what needed to happen next to fix the party’s institutional shortcomings and jumpstart its chances at a resurgence. They knew they wanted to build a Cadillac outside group with five-star organizational, strategic and fundraising components. Rove recalls it was Gillespie who said they had to get Law to run it.

“I said, ‘You’re nuts. He’d be fantastic but he’s not going to do it,” Rove said. “General counsel of the U.S. Chamber is one of the great jobs in Washington. He could go on to become general counsel of a Fortune 100 company. There’s no way in hell we’re going to get him...It was a huge pay cut.”

But when Gillespie approached Law about the prospect of a new project that could revitalize the Republican Party, he leaped at it.

“He said he was enjoying the job at the Chamber. He actually wasn’t, but he said he was,” Rove said.

Law jokingly remembers it as his midlife crisis moment: “I just turned 50...Buy a sports car or start a super PAC.”

A more colorful McConnell

With the seismic January 2010 Supreme Court ruling that corporations and outside entities could spend unlimited money on elections, American Crossroads and Crossroads GPS, its nonprofit policy offshoot, were born.

But without a clear sense of their viability, Law kept things lean at the outset, subletting office space like a start-up and eschewing fundraisers who requested big fees.

“There were holes in our walls,” said Jonathan Collegio, one of Law’s first hires at Crossroads. “The wire ran outside of the wall to plug the TV in.”

It was all meant to signal to donors their investments wouldn’t be wasted on perks or amenities.

“If you gave money to Crossroads, 99% of it was going to hit the target,” Collegio said.

Crossroads raised $70 million during the 2010 cycle, helping Republicans sweep back a record amount of House seats and knocking off bewildered Democratic incumbents with the muscle of an unprecedented advertising budget.

But in addition to setting the strategy and hauling in the cash, Law, a music major who plays an electric piano and counts himself a fan of EDM, got involved in the creative aspects of Crossroads, weighing in on details as fine as the font coloring and music used in their advertisements.

In one instance, Law personally helped write the jingle that accompanied a memorable web video targeting the chair of the Democratic National Committee as “Debbie Downer.”

“Steven is a more colorful McConnell,” said Larry McCarthy, a veteran Republican admaker who has worked for McConnell and Crossroads. “He is a man of strong creative opinions and he’s not shy about expressing them.”

The march to take back the Senate took longer than anticipated due to the Tea Party movement and a flurry of messy anti-establishment primaries from 2010 to 2012. But Law was always thinking about how to improve the Republican ecosystem, helping plant the seeds for the GOP opposition research group, America Rising, which will turn 10 years old next year.

After the GOP finally clawed back the majority in 2014, McConnell sent word through another top lieutenant, Josh Holmes, that he could use a separate super PAC brand solely dedicated to maintaining Senate control to counter Democrats’ Senate Majority PAC.

Law worried that adding another group would confuse donors; McConnell thought it would widen the aperture of potential contributors. In January 2015, the Senate Leadership Fund was established and eventually Law surmised that McConnell was right.

With the surprise ascendance of Donald Trump and his chaotic candidacy dominating the cycle, most prognosticators saw Democrats on a path to wresting back Senate control in 2016. But Trump’s victory wouldn’t be the only surprise that night.

In the final week of the campaign SLF had four polls showing Pennsylvania Sen. Pat Toomey losing his re-election bid. Instead of abandoning him, Law solicited fresh capital from donors, doubling-down on advertising that soiled Democrat Katie McGinty’s image with voters. Toomey won by just over 1% and now suggests SLF’s late infusion might’ve been the difference.

“My campaign was being outspent on television and most public polling showed me trailing,” Toomey told McClatchy. “Despite this, Senate Leadership Fund and Steven Law never gave up on me or my campaign.”

With Democratic candidates increasingly outraising Republicans through the strength of their liberal low-dollar donor network, Law sees his work as all the more important. In the spring of 2020, Law broke his own rule against spending too early and appropriated $30 million in places like North Carolina and Iowa.

“He looked at what the other side was doing and was like, ‘We can’t sustain this. Iowa was crazy, they just kept on spending money,’” said McLaughlin. “It wasn’t planned on, it was new money.”

Looking back, Republicans believe it probably saved Sens. Joni Ernst in Iowa, who ended up winning handily, and Thom Tillis in North Carolina, who survived much more narrowly.

“I think without our countervailing financial impact, I think you would’ve seen a number of our races washed out,” Law said.

Super PACs don’t generally receive the credit for a surprise outcome. After all, they can’t control the quality of a candidate or unforced errors by the campaign due to the ban on direct coordination. Similarly, they also have enough distance to avoid blame for losses, like the twin defeats sustained by Republicans in Georgia earlier this year that handed Democrats their slimmest possible majority.

But no matter how far and wide the 2022 Senate map expands, both sides of the aisle expect Law to be there with an arsenal that’s usually unmatched.

Asked if he ever has any qualms about the amount of money he’s pouring into purely partisan politics, Law said he’s guided by the late Charles Krauthammer’s writing in his book, “Things That Matter.”

“If you get the politics right -- and in that I include policy -- the other important things in life can go well. But if the politics are wrong, the rest of life will suffer too,” Law said. “Those who contribute to us -- and I presume the same about Democratic donors -- believe that investing in getting the politics right is neither frivolous nor wasteful nor unseemly, but the honorable work of democracy.”