We report the discovery of SDSS J0909+4449, an exceptional system consisting of a quasar at z = 2.788 strongly lensed by a group of galaxies at z ˜ 0.9 into three images separated by up to 14 arcsec based on archival data collected by the Sloan Digital Sky Survey, extended Baryon Oscillation Spectroscopic Survey, Beijing-Arizona Sky Survey, the Mayall z-band Legacy Survey, and the Gemini Telescope. We discuss two hypotheses on the nature of SDSS J0909+4449, i.e. a rare triply imaged quasar in the naked cusp configuration and a typical quadruply imaged quasar with the fourth image undetected in this data. We find that simple lens models can provide excellent fits to the observed image positions and the non-detection under either hypothesis. Deeper imaging data, spectroscopic observations, and follow-up light-curve measurements will be helpful in determining which hypothesis is correct and provide better constraints on the lens mass distribution. Nevertheless, given its unusually large image separations, SDSS J0909+4449 will be a unique probe for the mass structure and the underlying cooling and stellar feedback processes on group or cluster scales.