For days, like so many other people, I’ve been thinking about why the loss of Teddy Kennedy has hit me hard. There are the obvious reasons: from the larger than life sway the Kennedy family holds in Massachusetts most especially to Teddy’s (I’m going to call him Teddy) incredible contributions as a United States Senator. Of course, his isn’t a simple story; he wasn’t merely a straightforward individual. Being the youngest brother in a generation that rose early to power and influence and tragedy—though not the first generation to command influence—explains some of the inherent burden to being Edward Moore Kennedy. Being left behind had to have been its own burden, balancing the pressures of expectation—to serve country not just well but gloriously—to taking on leadership within a complicated family system, to doing all of this with phenomenal privilege. In terms of money, privilege meant Hyannis, sailing, skiing, hard drinking, and private planes. It was more than dollars, though. This is old tethered to more than financial bounty: Kennedy connotes political influence and legacies of many stripes, and also, purpose. No one could argue that the Kennedy clan has had access to too many get out of jail free cards. The partying ways, the playboy ways, seemed to come alongside a strong, principled, honorable sense of commitment to the country, an obligation—indeed, a passion—to serve. It is impossible to imagine being young, losing one’s brothers so publicly and so violently and then reckoning with finding a suitable place in the world.

Not surprisingly, people have extremely intense reactions to the Kennedys. The incredible outpouring over the past days—those on line to pay their respects and offer their sincerest thanks ran the gambit from wealthy to working class to poor—reveals the gratitude and admiration Teddy earned. But there were naysayers too, people angry about what was overlooked or nominally glossed over—things that would have stopped others from having any chance to rise to such glory—even when offering retrospective to his life. There were people who felt Teddy didn’t always stand up tall enough on certain issues. Given the towering heights the family enjoyed and the devastations and the overwhelming power, reactions to his passing can only be varied and fervent.

What I’ve been thinking about—along with my great admiration for Teddy’s Senate career, his contributions to my state, his critical support of Barack Obama, and the graciousness of his final years—is how many children of privilege relate, generally with more subtlety, to those being-Teddy-Kennedy contradictions. You can spin Teddy’s story many ways, including that after Chappaquiddick, he was granted a miraculous second chance. Depending upon how you spin the story, you can praise all he ended up doing with that—and other—second chances (including his spectacular union with Vicki, one makes me cry it is so moving), or you can curse the unfairness of operating outside the system and above the law. There is no way to argue against either narrative, because both are true.

Even in his final weeks, as Teddy championed health care—which he called “a right, not a privilege”—the irony lingers that his personal battle with brain cancer was fought by a team of doctors better than any money alone could buy. Don’t get me wrong: I am glad he could assemble a dizzyingly smart team to try to heal him. I would wish such expertise for all. And at the same time—in fighting for universal health care—the hoped for outcome isn’t that every single person can assemble all the greatest minds and resources; the hoped for outcome is that everyone will have enough health care to thrive and that the system can meet as many needs beyond well-care as possible. Access to health care for all will inevitably mean some tough choices. There are tough choices now, too.

We are currently experiencing the aftershocks of a period of rapid change in this country, one in which the rich—especially at the very top levels—really did get richer and the rest… not so much. Arguably, the increased concentration in wealth at the top levels is rising too quickly. Meaningful reform—health care, banking—are not forthcoming. Paul Krugman wrote in the New York Times this past week: “But it’s hard to avoid the sense that a crucial opportunity is being missed, that we’re at what should be a turning point but are failing to make the turn.” Krugman referenced a study, Striking it Richer, out of Berkeley that has charts depicting the trajectory. It seems completely clear that the kind of change we need involves a leveling of the playing field and for that to occur, those with privileg—extreme, not so extreme—will have to cede some in order for a successful next step in democracy complete with principles—“for all”—to remain within our collective grasp. On almost every front, we see how grabbing for more takes us further from securing a sustainable world: energy consumption, the size of new home construction, the obesity epidemic, big pharma, monopolization of the food industry, the insurance industry’s hold on Washington… and I could go on. Universal health care is one solid step, but not the end goal. To do Teddy proud—and possibly take pressure off of future generations of Kennedys to uphold such extreme legacies—we have to go much further. Rather than choosing smaller cars for a few years—in response to long gasoline lines—we have to choose smarter cars and invest in smarter transportation, such as railways and bicycle paths. In doing so, perhaps the nature of privilege itself begins to change.