The role of systems in addressing the needs of elderly and chronically ill populations remains a far from universal way of thinking, much less practice, in health care. Re-engineering the current fragmented system to align providers, patients and payment models to facilitate proactive management of conditions associated with advanced age and/or one or more chronic diseases – rather than responding to costly consequences of a health care system optimized for acute care conditions – will be a major challenge for all stakeholders. There are, however, promising success stories that are taking place in the United States today that may provide a model for improvement. The authors define the issues faced by the health care providers and payers that arise when providing care for the elderly and those with chronic conditions – issues that threaten to overwhelm the financial and human health care resources that exist to serve these populations. They define innovative ways of thinking about systems of care, and provide examples of unique systems that have applied theory into practice. These successful leaders may offer lessons in proactively managing complex health conditions, overcoming communication barriers and using technology to complement the necessary human touch that is essential to health care delivery.