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Barring some shocking eleventh-hour twist, Nancy Pelosi will almost certainly be voted Speaker of the House. Depending on how you look at it, that’s either good or bad news. On the one hand, Pelosi is undoubtedly an able hand at the practical aspects of the job, and in several high-profile episodes she’s successfully resisted parts of the Republican agenda and occasionally even the more right-wing elements of her own party. On the other, Pelosi is arguably the perfect avatar for today’s moribund Democratic Party: awash in money, steeped in conflicts of interest, hopelessly anchored to an illiberal and always-moving center, and pathologically unable to fully stand up for what should theoretically be its own principles — all of which makes her unsuited to leading the party in the current moment. Yet as Alexandria Ocasio-Cortez has pointed out, with a challenger to her left on the horizon — the lawmakers now opposing her, for one, are largely right-wing Democrats, some of whom are demanding changes to “revive bipartisanship” — Pelosi is poised to once more become the most powerful woman in the United States. Pelosi’s re-ascent isn’t a disaster — in a darker timeline, it could have been centrist Steny Hoyer in her place. But throughout her four-decade-long political career, Pelosi has amply demonstrated why the Democratic leadership needs to be challenged.

Family Ties While Pelosi started her political career relatively late, at forty-seven, her pedigree all but ensured she would become a major player at some point. Her father, three-term Baltimore mayor Thomas D’Alesandro Jr., was a Roosevelt Democrat who ran the party’s machine in the city, doling out favors for votes and giving the nod to aspiring politicians even in retirement. Her brother, Thomas D’Alesandro III, followed in their father’s footsteps for one term. Although Pelosi eschewed the family business for decades during her years as a homemaker and mother of five, this period of her life helped lay the foundations of her political career by providing the wealth and connections she would use to assemble power. The Pelosis moved to San Francisco in 1969, just as the city’s radical, countercultural politics had crested, and just as the Silicon Valley tech boom began its ascent. Her husband, Paul Pelosi, became rich from real estate investing and finance, while Pelosi started getting involved in Democratic politics, volunteering and raising money for the party. Pelosi has joked before that her family “were all christened into the Roman Catholic Church and the Democratic Party,” and the statement suggests where Pelosi’s highest political loyalty lies. Her friend, former California Rep. Barbara Boxer, noted that Pelosi never got involved in any of the state’s copious activist movements. “Her passion was always the Democratic Party as opposed to these issues one at a time, because she believed that the Democratic Party embraced these issues,” she said. Pelosi served in a number of volunteer positions, first managing Jerry Brown’s successful 1976 primary campaign in Maryland before serving as chair of the California state party, the country’s largest, through 1982, as well as overseeing the delegate selection process for the 1984 national convention. Four years later, Pelosi would run for Congress after being personally tapped by the family of the recently deceased Congressman whose seat she was running for. In doing so, she eschewed the typical route of first running for local office, instead basing her run on her status as one of the party’s preeminent fundraisers. Even at the time, Pelosi’s wealth was an issue, with some voters voicing doubts that she could relate to working people. But it was also a boon: Pelosi won a narrow plurality of the vote by spending $1 million, more than all the other candidates combined. And for all the hatred Pelosi attracts from the Right as the embodiment of decadent San Francisco liberalism, she won her first race by winning over the district’s Republican voters. Most of Pelosi’s early political career was laser-focused on a few issues of intense concern to her constituents. These included the AIDS crisis and matters important to the local Chinese community; according to Asian Week, Pelosi won the support of half of the respondents in Chinatown. It was on the back of the this that she became a champion of immigrant rights and a fierce critic of the Chinese government, even rebelling against Clinton’s attempts to upgrade the country’s trade status. By 2002 Pelosi became known as “the House’s leading advocate for human rights.” Pelosi’s other major initiative in this period was to privatize San Francisco’s Presidio, originally a defunct military base and later a national park. She shepherded legislation through Congress to turn management of the park over to a trust run by figures from the private sector, who were encouraged to lease buildings to commercial interests, exempt from government regulation of staff hires, requiring only that it “generally” adhere to the original Park Service plan. In doing so, Pelosi rejected calls from community and church groups, the city’s mayor, and even its board of supervisors to alleviate the city’s housing shortage by using the Presidio for public housing. She subsequently lost the support of the Bay Guardian, San Francisco’s progressive weekly, which ever since has refused to endorse her. “Pelosi has been bucking the Bay Guardian and like-minded voters for most of her fifteen-year career in Congress,” the Los Angeles Times wrote in 2002. Pelosi’s prodigious fundraising continued apace once she entered Congress. Two years in, she became the eighth-largest recipient of PAC money according to the Post, receiving over half a million dollars. At one point, Pelosi served as an auctioneer at a celebrity auction, literally selling off access to party bigwigs to the highest bidder. On the whole, Pelosi had a progressive record throughout the decade. She opposed the Gulf War, co-sponsored a single payer bill to preempt the Clintons’ health care plan, put forward legislation mandating aid to Haitian refugees, criticized Clinton for his balanced-budget crusade, and opposed his attempt to pass “fast track” legislation expanding his power to negotiate trade deals. She also voted against some of the lowlights of the Clinton era, including welfare reform and the immigration bill that helped create today’s deportation machine. She also voted for some of the lowlights, including the crime bill and the repeal of Glass-Steagall that helped deregulate the financial sector. Pelosi showed there were limits to how far she would buck her party. She co-chaired the committee that produced the Clintonite 1992 Democratic platform that included a capital gains tax cut, a “pay-as-you-go” requirement, and a focus on “individual responsibility.” She vacillated for weeks on NAFTA under pressure from her constituents and her president, ultimately siding with the latter. “Words failed to express our revulsion of your action,” said the secretary treasurer of the San Francisco Labor Council at the time. The decade also offered the first hint of what would become a theme in Pelosi’s career: the intersection of her private wealth and her political work. She was singled out in a Wall Street Journal report in 1994 scrutinizing lawmakers’ investments in IPOs, which pointed out that Pelosi’s husband had made a killing off a purchase of shares in computer software company Gupta. While several other lawmakers ended the practice in the ensuing controversy — the concern was that the IPOs, reserved by brokers for their most favored clients, were being laid open to lawmakers as a form of influence — Pelosi’s husband continued buying and selling IPO stocks for years. It would land her in substantially hotter water years later.

Resistance, Act I After more than a decade in the House, the new millennium saw Pelosi begin her ascent up the Democratic Party ladder, running for whip against longtime centrist nemesis, Steny Hoyer. She won. Like her political career as a whole, Pelosi’s victory was rooted in her ability to attract and dole out globs of cash to other Democrats. Tapping Bay Area tech companies, lawyers, and venture capitalists, Pelosi alone gave more money ($557,000) to House candidates than the entire House Democratic caucus combined and raised $1.1 million for the Democratic Congressional Campaign Committee. She had raised just short of $4 million for candidates in the preceding election, more than double Hoyer’s haul. Two years later, Pelosi rode that tsunami of cash all the way to the position of minority leader, raising a massive $7 million for Democratic candidates in that most recent election cycle. She violated campaign finance laws in the process, running two leadership PACs in order to “give twice as much hard dollars,” as the PACs’ treasurer candidly explained. Prior to the victory, Pelosi had been a fierce opponent of Bush’s policies, voting against his tax cuts, resisting the creation of a Department of Homeland Security, and becoming one of the most vocal critics of Bush’s march to war in Iraq, even as then-minority leader Dick Gephardt worked to give him a blank check to wage it (Unlike high-profile Democrats like Hillary Clinton and Joe Biden, Pelosi voted against Bush’s Iraq War resolution). Perhaps owing to fears among the party’s centrists over Pelosi’s liberalism, however, her climb up the ladder seemed to temper these views. Pelosi now talked about finding “common ground” and named “Do they grow the economy?” as the chief metric by which to evaluate economic measures. She ultimately bucked the rest of her colleagues in the House, including even Gephardt, to vote for Bush’s Homeland Security department. Mere days after taking the position, she told Tim Russert that “we stand shoulder-to-shoulder with the president in the fight against terrorism,” pledged to support Bush if he invaded Iraq, and refused to take a position on his surveillance of Iraqis living in the US, saying only, “I stand with the president in rooting out terrorism.” About this same time, Pelosi was secretly briefed on the CIA’s overseas detention centers and “enhanced interrogation” methods, including waterboarding, and raised no objections. Pelosi later offered up an ever-evolving series of explanations for this, but at best she was informed about it five months later and failed to do anything. An apoplectic Pelosi later — and commendably — scuttled a secret CIA plan to “interfere” in the Iraqi elections on behalf of moderate parties, so who knows how history might have been different had she mustered the same outrage over torture. Pelosi’s anti-Bush resistance was a mixed bag. On foreign policy, it was weak, with Pelosi and the Democrats passing a resolution praising Bush’s “firm leadership and decisive action in the conduct of military operations in Iraq.” (Pelosi made sure to give a speech criticizing it before voting for it, however). When Pelosi did criticize Bush, it was over not spending enough on homeland security, though as the war became more unpopular — and the antiwar movement gained strength — she and the Democrats took an increasingly forthright position against the war’s continuation. It was slightly better on the domestic front. The Democrats unveiled a tepid alternative to Bush’s tax plan in 2003 that combined extending unemployment insurance with several measures benefiting businesses, and put forward a platform in 2006 that was slightly more progressive — a $7 minimum wage, tax-deductible college tuition, lower drug prices, and an end to fossil fuel subsidies — but remained excessively cautious, particularly given that it once again included pay-as-you-go. According to one report, Pelosi specifically insisted that traditionally progressive measures like universal health care be left out of it. She did at least lead an (unsuccessful) united Democratic front against Bush’s Central American free trade agreement (CAFTA), attacking Bush for hollowing out the US industrial base, but years later made a deal with him to advance free trade agreements with Peru and Panama anyway. Pelosi was also instrumental in killing Bush’s radical and deeply unpopular plan to privatize Social Security, and under her leadership, Democrats passed a modest minimum wage increase, the first in a decade. Some successes were tempered, like when Pelosi personally watered down a prescription drug measure for fear that big pharma would derail it. In other ways, the party went backwards, as when she pushed Democrats to end their decades-long opposition to offshore oil drilling. Meanwhile, as Pelosi increased her influence over the party, so did moneyed interests. Together with her Senate counterpart, Pelosi ousted the Democratic member of the FEC most devoted to enforcing the McCain-Feingold campaign finance law, replacing him with a labor lawyer who had worked to block the law. Two years later, in 2005, she personally lobbied the FEC to neuter part of the law and allow politicians to raise unlimited amounts of money for groups campaigning for ballot measures, going against the advice of its own lawyer. What required this extraordinary step? Arnold Schwarzenegger, then the Republican governor of California, was pushing a ballot measure that would have taken the task of redistricting out of the hands of the Democrat-controlled legislature and put it into the hands of a panel of retired judges. In other words, Pelosi helped weakened campaign finance laws to make sure Democrats could keep gerrymandering the state. At the same time, the Democratic Party’s dependence on corporate fundraising intensified under Pelosi. She and then-DCCC chair Rahm Emanuel would harangue lawmakers who hadn’t paid their DCCC “dues” — fundraising benchmarks that Democratic Congress members must meet to sit on or chair committees, and which range from tens to hundreds of thousands of dollars. Pelosi, like her predecessor, would shame lawmakers by making public how much they had, or rather, hadn’t, raised. At one point, she threatened a senior Minnesota Democrat that he would miss out on a ranking position on the House Agriculture Committee, leading him to start taking large amounts of money from wealthy donors and business PACs. In 2006, Pelosi tried and failed to get rid of arch-rival Hoyer by endorsing conservative Pennsylvania Rep. John Murtha for his position. Murtha, who in the 1970s had come extremely close to being indicted in the Abscam bribery scandal (the same scandal that served as the plot of American Hustle) had been named as one “to watch” in Citizens for Responsibility and Ethics in Washington’s annual “Most Corrupt Members of Congress” report for using his position on a defense appropriations subcommittee to line of the pockets of one of his former staffers and the clients of his lobbyist brother. The whole episode made a mockery of her incessant “culture of corruption” attack line against the GOP.

Era of Reform Obama’s election in 2008 heralded the most consequential period of Pelosi’s career. With her speakership converging with Democratic control of the presidency and both houses of Congress, Pelosi was in a better position than arguably any previous Democratic speaker to make longstanding party goals a reality. The Democrats’ greatest accomplishment in this period was health care reform; however flawed, Pelosi was instrumental in rescuing it from even more fatal watering down. When Rahm Emanuel, ever the devil on Obama’s shoulder, urged the president to pass a drastically scaled down, piecemeal version of reform after the effort stalled, Pelosi convinced Obama to do otherwise, and proceeded to work overtime to get it passed. In the process, however, Pelosi killed the public option, despite earlier promising that no health care bill without it would pass the House. Under Pelosi, the House went on to pass a flurry of other progressive legislation, including financial regulation reform, fair pay for women, credit card reform, the DREAM Act, landmark climate change legislation, extension of CHIP, new campaign disclosure rules, ethics reforms, and a reduction in the crack/powder cocaine sentencing disparity from 100:1 to a “mere” 18:1. Not all of these passed Senate; some, like the last two, were still inadequate. Nevertheless, it’s an impressive record, particularly when paired with her rallying of the party behind the Iran nuclear deal years later. The flipside of this is that Pelosi, ever the party stalwart, also moved right in concert with the president. Previously criticizing Clinton for “playing right into the hands of the Republicans” by trying to balance the budget, she became a proponent of the deficit-cutting craze. After initially standing against the Obama-appointed entitlement-targeting Simpson-Bowles commission, one year later she decided that cuts to Medicare and other programs were on the table, because “at the end of the day the deficit has to be reduced.” She adopted GOP talking points and claimed Obama’s planned Social Security cuts would “strengthen” the program, before claiming this was a bluff, only to reverse herself again on the issue and quietly plan to muster votes for Obama’s ultimately doomed attempt at a “grand bargain.” To this end, she also backed making a “simpler and fairer” tax code for businesses and increasing domestic production for fossil fuels. (Indeed, Pelosi would later pass a spending bill that lifted the ban on US oil exports in return for solar and wind energy subsidies). Previously an antiwar Democrat, Pelosi now backed Obama’s illegal war in Libya and urged Obama to take military action against Assad, six years after she had courted controversy by meeting with the Syrian dictator and declaring “the road to Damascus is a road to peace.” In the Libyan case, she explicitly denied Obama even needed to get congressional authorization for the war, advocating for the kind of imperial presidency she had opposed under Bush. Indeed, when asked if the public should be informed when the government assassinates a US citizen via drone, Pelosi said, “it depends on the situation,” and that “people just want to be protected.” Previously a critic of government surveillance, Pelosi now became one of its most powerful defenders. When a bipartisan coalition moved to curtail the NSA’s collection of Americans’ phone records in 2013, Pelosi became the decisive force that killed the effort, aggressively lobbying Democrats to vote against it. This year, after complaining that Trump was attempting “thought control” and generally warning how dangerous he was, Pelosi voted to extend his power to carry out legally dubious surveillance on Americans through the NSA. Pelosi has said that Edward Snowden should be prosecuted for revealing the government’s vast, secret spying regime. Previously a champion of single-payer health care, Pelosi shifted her views to line up with the party’s presumptive 2016 nominee. “It’s no use having a conversation about something that’s not going to happen,” she said about Sanders’s single payer plan, adding that Democrats were “not running on any platform of raising taxes.” Pelosi still refuses to sign on to Sanders’s Medicare For All legislation, which one would think would be pretty safe to support from a seat in San Francisco. One thing that didn’t change was Pelosi’s connections to big money, which only deepened in the Obama years. By 2014, she had raised more than $100 million in a single election cycle, and nearly $430 million since 2002, ensuring her continued hold on the House leadership: in one election cycle, for instance, Pelosi outraised rival Hoyer by about 17 to 1. Pelosi continued complaining about dark money in politics even as she raised unheard of amounts from tech firms, venture capitalists, lobbyists, and various other large donors. “My money comes from very idealistic progressives who want to see good government,” she explained. “They have no agenda.” When asked if Silicon Valley firms like Uber and AirBnB “truly stand for the same things that you stand for,” she replied: “It doesn’t matter. I stand for them standing for whatever they want to stand for.” Pelosi and her husband’s personal finances also continued to intermingle with her political work. In a single year, in 2010, the Pelosis saw their net worth jump by 62 percent, largely on the back of her husband’s real estate investments and shares. The value of their Apple stock doubled, for instance, and by 2011, Pelosi owned more than half of the $1.8 million of Apple stock held by a few dozen lawmakers. In 2008, just as a bill aimed at limiting swipe fees on credit cards was making its way through the House, and just as Visa embarked on a massive lobbying and influence campaign to sway Pelosi against such legislation, her husband got a call from his broker inviting him to Visa’s exclusive IPO, which was closed to the public. Pelosi bought 5,000 shares at $44 each, whose value jumped by $20 two days later. Meanwhile, she chose not to bring the bill to the floor before Congress adjourned (a similar bill did eventually pass after originating in the Senate, however). Republicans would later try to pass a so-called “Pelosi provision,” barring lawmakers from using their office to access IPOs. In another case, the $50 million diverted by Pelosi to help build a light-rail project in San Francisco turned out to also be benefiting a four-story commercial building in the area owned by her husband (though unlike the credit card issue, that project at least had an important public benefit). Pelosi’s husband also invested heavily in green tech firm SunEdison just weeks before a major acquisition made its stock price leap by 29 percent, prompting speculation about insider trading, mostly from the Right. This was on top of money that Pelosi’s PAC was paying her husband and his firm, an arrangement that, while not illegal, is ethically questionable.

Trimming Sails Trump’s 2016 victory didn’t seem to have had much of an impact on Pelosi’s worldview. “I don’t think people want a new direction,” she told Face the Nation the month after the party’s loss. The Democrats’ new “Better Deal” platform, as tepid as it was in many respects, did show the party was slowly realizing the importance of class-based politics to take on the Trump agenda. But true to her words, Pelosi has clearly found it hard to let old habits die hard: when she introduced the platform in an op-ed, tax credits for businesses was the policy she led with. Pelosi has continued championing pay-as-you-go and, even worse, following the Democratic midterm victory is reportedly considering a disastrous rule change that would require a three-fifths supermajority to raise taxes on most Americans, a move that would make a host of progressive legislation impossible. Meanwhile, she’s remained distinctly unenthusiastic about the idea of Medicare For All, neither co-sponsoring nor endorsing the policy, and stressing after the Democratic takeover of the House that she and other Democrats would be focused on fixing and protecting Obamacare. There’s another reason why Pelosi can’t be counted on besides her reflexive political caution: her wealth. Not only is Pelosi, one of the richest members of congress — as of 2015, she was worth over $100 million, according to the Center for Responsive Politics — but those riches are tied up in the very corporate entities the Democratic Party will eventually have to take on. This year alone, according to financial disclosure reports filed by Pelosi, she and her husband have invested anywhere between $150,000–$350,000 in Facebook, $250,000–$500,000 in AT&T, and a whopping $1.5–$1.6 million in Amazon, as well as $1.7–$3.5 million in Apple (though they also sold between $1.35–$5.75 million worth of stock in the latter). It’s hard to imagine someone with this portfolio launching a serious campaign against corporate America, let alone breaking up the monopoly power of these specific companies. Regardless, Pelosi’s fundraising prowess all but ensures she’ll be speaker once again. There’s no other Democrat who touches Pelosi in how she hoovers up cash and dispenses it for loyalty, and a group of big money donors has already threatened House Democrats with keeping their wallets shut if Pelosi is kept from the speaker’s chair. That means any challenger from her right is a non-starter — but it could also be a formidable roadblock for any future challenger from her left.