Meg Whitman licks her goggles, steps up to the ledge, places one hand on the concrete, and hurls herself, pencil-straight, into the turquoise-blue water. She’s off in a brisk freestyle crawl—“Race pace!” yells a coach—covering close to half the pool before coming up for air. It’s 7 a.m. at the outdoor community pool in Menlo Park, Calif., where the CEO has been swimming almost every morning since January 2011—just after she lost the race for California governor, just a few months before she took over Hewlett-Packard at the darkest point in its history. She’s not just doing laps; it’s a “boot camp–ish” routine of breaststrokes and freestyle sprints and flip turns, and Whitman, in lane six of the 10-lane pool, is at the center of it all.
“I needed something to take my mind off losing,” she says of her decision to jump back in after three decades away from competitive swimming. By the time she emerges after an hour, glistening and flushed, she’s beaming; standing beside the water in a black, pool-worn one-piece bathing suit, she puts her hands on her hips and turns her face to the morning sun. It’s the ultimate power pose: This is what winning looks like.
The 61-year-old Whitman hasn’t exactly won yet. She holds a unique distinction, not just as a woman running a Fortune 500 company but as the only woman to have run more than one—first eBay, now Hewlett Packard Enterprise. (Irene Rosenfeld, the outgoing CEO at Mondelez, ran a predecessor of the same company, Kraft.) Yet today, about five years after she laid out a five-year plan to rescue HP, her success there is far from assured.
Nearly two years ago, Whitman led Hewlett-Packard through the biggest corporate breakup by revenue in history, cleaving the $103 billion company into two: HP Inc. (hpq), where she recently stepped down as chairman, and Hewlett Packard Enterprise (hpe), where she remains CEO. At HPE, which sells servers, cloud-computing software, and “Internet of things” networking systems for businesses, Whitman has continued slicing off divisions and coaxed profits into rising. But HPE’s revenue has shrunk to an estimated $33 billion this year, and she’s not positive she can get it to grow again. Meanwhile, HP Inc., the stodgier printer- and PC-maker, has been posting near-double-digit sales growth and upstaging HPE’s stock.
“I might be the only CEO in America who wants to run a smaller company,” Whitman likes to say. But it’s not clear how much longer she’ll do that. In June she promoted Antonio Neri, head of HPE’s enterprise group, to president, positioning him as her likely successor. In August she was a top contender to replace Travis Kalanick as CEO of Uber, in which Whitman was an early investor—a job that could have teed her up to eventually lead an unprecedented third Fortune 500 company. (The ride-sharing giant went with Dara Khosrowshahi.) And recently she’s been leading on a bigger stage. A lifelong Republican, Whitman switched her support to Hillary Clinton three months before last year’s election—she was the only Fortune Most Powerful Woman to publicly campaign for a nominee—stoking speculation that the former gubernatorial candidate would reenter the political arena. “Frankly, I think a leader of every organization now needs to stand up and be counted,” Whitman says. “History will judge.”
Whitman is still most celebrated for her decade at eBay, which she grew from oddball dotcom startup to e-commerce powerhouse. But the reputation she earned there is the opposite of who she’s become: a turnaround CEO, the grownup who could clean up HP’s mess—and why not Uber’s too? The cynic’s view is that she’s a one-hit wonder, boxed in at a company whose glory days are long behind it. Now, confidants think the intensely competitive Whitman wants another chance to solidify her legacy. Says Neri, “Meg does not like to lose, trust me; she does not like to lose.”
A hard hat: That’s what Whitman’s new coworkers gave her when she became Hewlett-Packard’s CEO. Covered in stickers bearing idioms such as “Catch a falling knife,” the construction gear sent a not-so-subtle message: In this job, use extreme caution.
When she took over in September 2011, HP was enjoying its best year ever, with sales peaking at $127 billion. But it didn’t feel that way. Her predecessor, Léo Apotheker, had lasted barely 11 months; he had succeeded Mark Hurd, who left Hewlett-Packard after being accused of sexual harassment and expense account discrepancies. (Hurd, now co-CEO of Oracle, has always denied wrongdoing.) And Apotheker’s $11 billion deal to buy British software company Autonomy would soon go down as one of the worst acquisitions in corporate history, leaving HP with a hangover that included an $8.8 billion write-down.
Whitman, who joined HP’s board in early 2011, turned down the CEO job the first time it was offered. The wounds from her most recent leading role were fresh: As the GOP nominee for California governor, the billionaire had spent 2½ years campaigning and $110 million from her own pocket, only to lose decisively to Jerry Brown in 2010. (“This is really not good,” Whitman’s neurosurgeon husband remarked upon catching her watching daytime television after the election.) But after a stealth meeting in New Jersey on Sept. 11, 2011, where the board voted to oust Apotheker, Whitman and fellow director Marc Andreessen were on a plane back to San Francisco when the venture capitalist cornered her with a recruitment pitch. “Two hours in, something in her eyes changed,” Andreessen recalls.
Drawn by what Andreessen calls noblesse oblige, Whitman recognized an opportunity to revive the faltering legacy of the company that birthed SiliconValley: Hewlett-Packard, founded in 1939 in a Palo Alto garage.She had neither tech expertise nor B2B sales experience, but she summoned a sense of patriotic duty: HP was important, she told employees—to them, to the technology industry, and to America itself. “It had been a long time since the great days of HP,” says Ray Lane, an HPE board member and former HP chairman. “She went in and got it to remember its groove.”
Her first changes were cultural. Whitman doesn’t hide her disdain for the way Hurd—who kept all but his inner circle at arm’s length—ran things. On day two she peeled off the smoke-tinted window film that shielded the C-suite from view and tore down fencing around the executive parking lot. As someone who never had a corner office—or any office—at eBay, she moved everyone to cubicles and plunked down in one herself. Getting staff to open up was like pulling teeth, Whitman says: “The company was pretty shell-shocked, honestly.”
HP’s problems, she found, were even greater than she had fathomed. Whitman recalls a vacation trekking in New Zealand where she was without cell phone service for almost a week. She exited the wilderness to a string of missed calls from her CFO, who broke the news that revenue and operating income would be billions of dollars lower than expected. In -November 2012 the company’s stock sank below $12, the nadir of her tenure.
One idea that wasn’t on her rescue road map, but that some investors favored, was splitting the company. Appointing a red team and a blue team to argue the pros and cons, Whitman initially resisted a split. Instead, she looked for efficiencies. In total, she’s eliminated some 75,000 jobs between HP and HPE. Still, customer requests went unresolved in HP’s “technology supermarket,” so she promulgated a new motto: “Run to the fire.” Some HP managers found Whitman’s directives patronizing. She reeled in employees who worked remotely. A punctuality zealot, she’d chide staff for starting meetings a couple of minutes late. Some managers were put off when she personally checked their travel schedules. Says one former exec, “We were all adults there.”
Whitman had predicted 2014 would “be the year you’ll see real recovery and expansion.” But by the time it arrived, a strengthening dollar had sapped international sales, price wars had heated up, and revenue and profits had continued to contract. Amid the bad news, Whitman joined Team Breakup: In October 2014 she announced HP would split in half. “It was so obvious to me that these companies were going to be better off alone and they could go faster,” she says.
The old HP, for one, might never have gone to Mars. A few months after becoming CEO, Whitman dropped in on HP’s R&D laboratory and asked, “You got anything we can sell?” The engineers showed her a curiosity that had been seasoning in their skunkworks since 2003. A supercomputer built with an unprecedented 160 terabytes of memory—equivalent to 20,000 laptops—they called it simply “The Machine.”
Today, The Machine, now part of HPE, is the largest R&D project in the history of Hewlett-Packard; Whitman estimates the total cost at more than $500 million. Veteran lab rats consider it their biggest breakthrough since the laser-jet printer. Already its computing prowess is being used to process genetic research data 100 times faster; HPE engineers hope it will one day travel on Mars missions to empower far-flung astronauts to run experiments without contacting Earth. That said, the term “moonshot” is largely eschewed at HPE. With fingernail profit margins compared to Google’s and Apple’s, the company can’t afford to frivol. “We’re super-excited about it, but we have to commercialize it,” Whitman says of The Machine.
Running a smaller company has freed up Whitman to pitch real-life products. She spends 70% of her time meeting with customers, she says. What she lacks in hardware knowledge, she makes up for with her Rolodex: “She hadn’t sold CEOs servers before, but she knew all the CEOs,” Andreessen says. Whitman cold-calls customers so often that some are initially standoffish, believing they’re being punked. “The first time it happened, I thought, gosh, that customer is so unfriendly,” she says. Three minutes after hanging up, the customer emailed her: “I just got a call from someone who’s impersonating you!”
Still, there are lingering doubts that Whitman’s pavement pounding will restore HPE to an upward trajectory. This year, HPE divested its enterprise services and software divisions, part of what Whitman calls her “very focused strategy.” But even the CEO doesn’t always sound convinced it will work. Driving to work after her swim, she tells Fortune, “I think we need a couple more years to sort of prove out the revenue growth thesis.”
It’s not just Whitman’s legacy at stake, but also that of the company she leads. She has increased value for shareholders, but while each share of HP held since she took over has returned 120% (inclusive of the separation and spinoffs), that lags the S&P 500’s 149%. What’s more, she has boosted share price by dismantling a business. “In tech, a rule of thumb is, if you’re not growing, you’re dying,” says Steven Milunovich, a managing director at UBS and a longtime enterprise tech analyst. “She obviously wants to be on the right side of that, but it’s going to be a struggle.”
The competitive landscape, meanwhile, remains brutal. While many businesses are moving data to the cloud (using providers such as Amazon and Microsoft), HPE caters to companies that want on-premises storage. That market is slow-growing and fragmented, and HPE is neck and neck with Dell EMC and Cisco, limiting the prices it can charge. The struggle is testing Whitman’s mettle, and as the company shrinks, some former colleagues now see her as merely a financial engineer, gifted at execution but lacking vision.
Whitman’s advocates praise her for making the tough choices necessary to assure Hewlett-Packard’s future. Still, even defenders see the best-case trajectory under Whitman as one of soft landings, not interplanetary ascents. “The question is, could you have gotten your mojo back, and could HP have been great again as a $100 billion company?” asks Lane, the board member. “I don’t think so.”
For a leader familiar with the hard knocks of politics, Whitman has been unafraid to flip-flop. Deciding to split HP was one reversal; another was her Democratic defection after Chris Christie, her GOP candidate of choice, bowed out. Her courtship at scandal-plagued Uber may have been another.
In July she publicly took herself out of the running for Kalanick’s job, tweeting, “Uber’s CEO will not be Meg Whitman.” As an investor in the startup, she had advised Kalanick and his deputies for years, and after his June resignation she had offered her counsel again. Some on the board saw in her his ideal replacement, despite, she claims, her lack of interest. “I wasn’t that attracted,” she told me in mid-August. Though she can see why they’d want her: “I have marketplace experience, I have political experience, I have big complex experience, and I’ve changed cultures. Right? So, there’s sort of a natural, like, ‘Wow, Meg would be great.’”
A week after our meeting, it seems, Whitman warmed to the idea as well. On the evening of Friday, Aug. 25, following Uber’s interviews with other candidates, two board members called Whitman. What would it take, they asked, for you to reconsider? On Saturday she gave her ultimatums—including resolving the board’s lawsuits and installing better governance.
Uber hired Expedia’s CEO, Khosrowshahi, instead. The ride-sharing company’s growth possibilities, Whitman said in a statement afterward, “remind me of eBay in its early days,” but “it wasn’t the right thing.” She reasserted her commitment to HPE, but she didn’t dispel the perception that some part of her would rather work for an Uber. Some expect she could leave HPE by the end of the year. Heidrick & Struggles, the headhunting firm that conducted Uber’s search, wouldn’t comment on Whitman’s prospects, citing its “policy of not commenting on candidates or companies engaging in a search.”
So what’s next for Whitman? “She’s born to run large organizations,” Andreessen says. “I think she’s happiest when she’s doing that.” Which raises the question of politics: There are few organizations larger than the United States, after all. “I wouldn’t be surprised if Meg ended up the first female President,” says Bob Kagle, a cofounder of venture capital firm Benchmark, who helped recruit Whitman to eBay. Indeed, Whitman says she saw elements of herself in Clinton—members of “the same generation of women who were pioneering.” After rebuking Donald Trump last year as a “dishonest demagogue,” Whitman refused a post-election invitation to join one of his now-disbanded business councils. She has since slammed Trump’s actions on the Paris climate accord, white supremacist violence, and immigration. She deflects accusations of betrayal from Republicans. “I haven’t turned my back on the party,” she says. “I would say maybe the party has turned their back on me.”
Whitman won’t rule out being CEO of another company; she had ruled it out after eBay, she points out, and now look where we are. Ask her whether she’d run for President, however, and a look like she ate a sour cherry comes over her face. A political appointment, maybe, but running for office? “I’m definitely not doing that.” But given Whitman’s history, you can never say never.
A version of this article appears in the Oct. 1, 2017 issue of Fortune with the headline “Boxed In.”