Modest inquiry exists to elucidate why donors make large contributions to community colleges. Of every charitable dollar donated to education, two-year colleges receive 2 to 4 cents. This grounded theory study included 30 major donors to 23 colleges in 18 states. The questions were comprehensive: why donors and how donors make major gifts; internal and external factors, and how they work together; important synergies for cultivation, invitation, and stewardship; and why contributors choose community colleges. Six themes emerged: family history and role modeling; relationships with the college and its leaders; the desire to make a meaningful difference; the institution's role as an economic driver; a wish to give back; and donor recognition tailored to each individual. Forty percent of donors who made six- and seven-figure gifts were never invited to contribute; these extraordinary donations were unsolicited. The findings also suggest myriad recommendations for practice. Opportunities and models exist for staff to understand what inspires each unique donor. Volunteers may engage through storytelling and activism. Connections can deepen through core mission work. Colleges may expand interaction with students and faculty through shared experiences. Nurturing close relationships with major benefactors may help to engage their circles of influence. Leaders should challenge the myth that alumni give only to universities. Involving families may result in allies today and contributors tomorrow. College retirees often are excellent prospects. Donors prefer personalized recognition. Professional advisers can serve as influencers, potential conduits, and roadblocks. The two-year college fiscal model speaks to bottom-line donors. And the crucial message? It pays to ask. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]