Melanie Sloan, executive director of the left-leaning Citizens for Responsibility and Ethics in Washington, had a close relationship with her biggest funder, billionaire insurance mogul Peter Lewis — but not with his three children or his younger brother.

So, when Lewis suffered a heart attack after a two-hour workout late last year and died unexpectedly at age 80, his family’s money suddenly stopped flowing to CREW, dealing the watchdog group a devastating blow.


Indeed, Lewis was one of the most significant funders of the institutional left — donating a combined $300 million over the years to liberal organizations, including the American Civil Liberties Union, the Center for American Progress, Media Matters and CREW, among others. Yet he did not leave a dime to any of them, nor to any of the universities and apolitical charities to which he had given another $300 million. And his children, who inherited most of Lewis’ fortune, haven’t given significantly to any of the political groups, despite assiduous courting by some of them.

“It was a huge loss for CREW and also for the progressive movement,” said Sloan.

Now, Lewis’ passing and those of a pair of Republican sugar daddies around the same time have become cautionary tales for political organizations across the spectrum, sending them a message about the importance of cultivating their donors’ children and younger spouses before it’s too late.

Since federal courts struck down key campaign cash restrictions in 2010, a few dozen super-rich activists have gone on a historic spending spree that has reshaped American politics. The group skews older and male, and a single death in its ranks can fundamentally reorder the political landscape.

“Obviously, I knew that he was older and that he had his health issues, but he was always really vibrant and on the go, never frail,” Sloan said of Lewis. “I always knew that Peter was not making bequests to his groups — that the money was going to be left to his kids. So I wasn’t surprised that he didn’t leave anything for us, but that doesn’t mean it wasn’t a shock.”

Like Lewis, neither Houston homebuilder Bob Perry nor billionaire Dallas investor Harold Simmons left much in the way of a political money succession plan, and their 2013 deaths shook the financial foundation of the right. The pair had combined to donate $132 million in federal contributions, including $44 million to Karl Rove’s American Crossroads super PAC.

“When they lost those two donors last year, it was really debilitating,” a prominent conservative fundraiser said of American Crossroads.

Thus, the most influential political money networks on the left and the right have increasingly encouraged their donors’ kids to attend the closed-door confabs that serve as de facto private conventions for the big-money set, complete with strategy presentations from operatives and get-to-know-you sessions with the most in-demand politicians.

Chase Koch, the 37-year-old son of billionaire industrialist Charles Koch, has been spearheading an initiative to involve the children of wealthy contributors in the Koch brothers’ vast political network, partly by holding special events for them at the network’s twice-annual donor seminars.

Next-generation participants have included Rebekah Mercer, the 40-year-old daughter of hedge fund billionaire megadonor Bob Mercer, as well as one of the daughters of Las Vegas casino mogul Sheldon Adelson. Adelson, his daughter, and his wife, Miriam Adelson, attended a June 2012 Koch seminar in Carlsbad, California, at which the casino owner told attendees that he hoped his daughter would one day take over the family’s political portfolio.

The fate of the family’s $37 billion gambling fortune has become an increasing concern for big-money conservative operatives, who worry privately about the health and erratic political decisions of the family’s 81-year-old patriarch.

Miriam Adelson, who is 69, sits in on political meetings and has been involved in key decisions, according to operatives who have assiduously courted her as a guardian of the Adelson political legacy.

“I’ve always dealt with them as partners — equal partners where it was a joint decision,” GOP lawyer Randy Evans said of Miriam and Sheldon Adelson in an interview at Adelson’s Venetian Resort Hotel and Casino this past summer. Evans has met with the Adelsons several times in his capacity as a top adviser to Newt Gingrich, whose political career the Adelsons have subsidized with nearly $30 million over two decades. “I can just remember meetings where I walked in and [Miriam] would dive right into” inquiries about a candidate’s position on the family’s pet issues, said Evans. “You could forget whatever it is you planned to say, because you were there to answer questions.”

Asked whether Miriam Adelson would give as much if her husband passed away, Evans was careful. “I don’t think that the Adelsons’ passion for Israel, for stopping the legalization of marijuana, for card check, for the kinds of issues that are of critical importance to them, will stop regardless of what happens.”

On the left, the Democracy Alliance major donor club has endeavored to make big-money politics a family affair, with mixed results. The club, which holds twice annual meetings, requires its members to pay annual dues of $30,000 and contribute a total of at least $200,000 a year to recommended groups.

These were all working-class guys who became fabulously wealthy, and their children inherit a different dream because of where they’re born and how they’re born into it.

The sons of founding members Lewis and billionaire financier George Soros had traveled the country recruiting donors to join the club before it launched in 2005.

Jonathan Soros has continued to be active and has played a major role in liberal politics more generally, as well as — perhaps ironically — the effort to limit the role of money in politics.

Yet Jonathan Soros said he had “no interest” in discussing how his father’s big-money political activism affected him.

Other Democracy Alliance kids on the group’s member rolls include Susan Sandler, the daughter of founding members Herb Sandler and the late Marion Sandler, and Cynthia Ryan, the daughter of Boston billionaire investor Vin Ryan.

The Sandler family foundation has given more than $650 million to progressive causes through the end of 2013, and Susan Sandler was recently elected to replace Cynthia Ryan on the board of Democracy Alliance. It also includes a 36-year-old tech heir named Farhad Ebrahimi, who has been involved with a group called Resource Generation that encourages rich young people to get involved in philanthropy. The wealth he received from his father and namesake, a former co-owner of the software company Quark, is “much, much more than I’ll ever need,” Ebrahimi wrote in a 2010 blog post explaining his philanthropy. In it, he compared his father to “an industrious squirrel who continued to collect nuts — despite the fact that we already had more than enough for winter. And so I made a promise to myself that, by the time I hit thirty, I would get into the nut redistribution business.”

It’s not uncommon, of course, for kids to reject their parents’ deeply held political beliefs, particularly if they feel they’re being foisted on them. Thus, liberal operatives have tried to capitalize on generational cultural shifts to woo the kids of rich conservatives.

Weston Milliken, one of the sons of South Carolina textile billionaire Roger Milliken — who funded The American Spectator magazine during its 1990s crusade against Bill and Hillary Clinton and has been credited with providing the cash behind Richard Nixon’s racially polarizing Southern strategy — is a member of the Democracy Alliance.

Weston Milliken co-hosted a panel at last month’s Democracy Alliance meeting called “Southern Discomfort” that, according to an agenda, focused on fighting policies in Southern states deemed “harmful policies to people of color, women, the LGBT community, and organized labor.”

Milliken, who is gay, “is clearly avenging the sins of the father,” said one Democracy Alliance player familiar with Milliken’s involvement.

The Democracy Alliance also welcomed Philip Munger as a new member this year. He’s the son of Warren Buffett’s Berkshire Hathaway colleague, billionaire Charlie Munger, who has donated primarily to conservative causes and whose other son and namesake is a leading GOP donor. And the club courted Laura Ricketts, a top bundler for President Barack Obama whose billionaire father, Joe Ricketts, founded TD Ameritrade and was a major donor to Mitt Romney and conservative causes. Laura Ricketts, a major donor to gay causes, was listed on a document obtained by POLITICO as among the “Prospects Possibly Attending” the club’s March conference in her hometown of Chicago, where her family owns the Cubs.

It’s not clear whether she attended the convention for liberal donors. But her brother, Pete Ricketts, attended the April 2013 donor seminar hosted by the conservative Koch brothers. A significant GOP donor in his own right, Pete was elected governor of Nebraska last month. And their other brother Todd Ricketts is a leading GOP super PAC donor who has broken with the party orthodoxy to support gay marriage.

While the Ricketts clan has split all over the political map, the tendency of sons and daughters of conservative megadonors to gravitate toward the other side presents a great opportunity for the left, asserted Craig Kaplan, a prominent New York Democratic donor who was a guest at the Democracy Alliance’s Mandarin meeting and also happens to be an estate attorney.

“This is a function of generational change and point of view,” he said. “The generation that is dying out, especially on the right, is ideologically driven, and it’s not clear that there’s as much appetite for fundamentalist Christian views or the narrow financial conservatism among their offspring.”

Nonetheless, Stan Hubbard, a Minnesota billionaire and GOP megadonor, said his children, who run parts of the family’s media empire, “are more conservative than I am by a big margin, because they’re probably smarter than I am.”

And while he once invited one of his children to a Koch seminar, he acknowledged: “I can’t dictate to my children or grandchildren what to do. It just so happens we all happen to be pretty much in agreement.”

Jonathan Lewis, who is 56, initially followed a political path very similar to that of his father, Peter. He joined the board of Media Matters, a core Democracy Alliance group, and he and his father were fixtures at early club meetings.

“It was like a father-son thing that they did together,” Sloan said.

But Jonathan Lewis grew disenchanted in 2009 with what he saw as the timidity of mainstream liberal groups on the gay rights fights that animated his political involvement. Lewis, who is gay, dropped off the Media Matters board and out of the Democracy Alliance.

Lewis did not respond to interview requests, but his longtime political adviser, Paul Yandura, explained that “Jonathan is not interested in going to big meetings, or getting invited to tea at the White House.” He added: “For many years, we had tried to get people elected and play nicely within the system, and still nothing was happening, so we undertook to create such a sh—storm that something would have to happen.”

The younger Lewis vexed Democrats and mainstream gay rights groups alike by almost single-handedly bankrolling a group called GetEQUAL, which catalyzed the fight against “don’t ask, don’t tell” by staging protests in which gay veterans handcuffed themselves to the White House fence. And he joined with pro-gay-rights Republican megadonor Paul Singer to bankroll an effort to pass federal legislation protecting gays and lesbians from workplace discrimination.

“Many people whispered that Jonathan was wasting his money, while privately thanking him for having the courage to stand up for what was right,” Yandura said, adding that Lewis always discussed his giving decisions with his father, who sometimes matched them.

Father and son were aligned in giving to groups supporting marijuana legalization. Peter Lewis’ philanthropic adviser of 27 years, Jennifer Frutchy, called the marijuana legalization movement her late boss’s “largest legacy.” An avowed marijuana smoker until his death, Lewis “played a huge role” in the tide of decriminalization and legalization taking hold across the nation, Frutchy asserted.

“Peter was a bit of an iconoclast,” she said. “He went all in on his philanthropy when he was alive, but he really left it for future generations to decide what’s next, because he knew that needs changed, that circumstances change and that leadership changes.”

Jonathan Lewis continues to support legalization efforts, Yandura said. But he hasn’t been as generous with CREW.

At some point after Lewis’ funeral, which took place last year on a bitterly cold day in his native Cleveland, Sloan penned a letter to Jonathan Lewis and to Peter’s 68-year-old brother Dan expressing her condolences and gently trying to start a conversation about continuing the family’s support for CREW.

“I got a polite note back saying they were not considering funding requests at that time,” said Sloan. Her group, which had about 15 employees and a $2.5 million budget, suddenly found itself in financial trouble.

Less than a year later — facing the loss of Lewis’ contributions and other challenges — CREW was folded into the fleet of better-funded nonprofit groups run by the conservative-turned-liberal enforcer David Brock.

It’s relatively rare for wealthy political activists to leave behind major bequests to their favorite causes. More often, they’ll put their cash into a foundation or trust that requires heirs to give a certain amount to charitable causes but don’t specify which ones.

“What’s unique about Peter is that he left full discretion to his kids to decide, which is consistent with his belief in individual autonomy and liberty,” said Anthony Romero of the ACLU, who was close to Lewis and spoke at his funeral, as did Frutchy. It drew many of the leaders whose outfits benefited most from his largesse, including Sloan and CAP founder John Podesta.

The ACLU had received about $3 million a year from Lewis until his death. While Romero said he “tried mightily” to persuade his benefactor to leave an endowment, he said Lewis told him, “I don’t believe in giving from the grave.”

Romero refrained from soliciting Lewis’ heirs for a year after his death to give them time to grieve and to mull their philanthropic goals. But he conceded that the loss of Lewis’ annual donations “left a huge hole in our budget.”

It’s illustrative of a bigger challenge for groups like the ACLU, three of whose top four donors are in their 80s.

“These were all working-class guys who became fabulously wealthy, and their children inherit a different dream because of where they’re born and how they’re born into it,” Romero said, though he added some “grow up learning about the importance of giving back. Philanthropy is also something that comes to individuals late in life, and it’s very rare that you find 20-somethings of enormous wealth who are giving away large sums of money.”

While he wouldn’t comment specifically on any efforts to woo Lewis’ children, Romero said, “The Lewis family will make the right decision about what makes sense for them. And what made sense for Peter may not make sense for his kids.” He added that, in general, “Just because someone might have a liberal father doesn’t mean their kids will be liberal as well.”