Population projection models based on long-term trends in regeneration and tree survival can be used to predict the future stability of swamp forest species using water management. Population growth and regeneration of a foundational tree species in North American cypress swamps (Taxodium distichum) were compared in the Cache River watershed of southern Illinois USA over several decades. This study examined T. distichum population growth in several regional swamps within the Cache River watershed along a moisture gradient to model growth, stability, or decline based on data of life history stage transitions, using data from the following time periods: the 1990s, 2002–2011, and 2012–2022. Using data from the 1990s, T. distichum populations in Crawford Tract in Buttonland Swamp were projected to increase over time because of the high frequency of juvenile stages at elevations with growing season drawdown and winter flooding. The situation in Crawford Tract had changed by 2019–2021 because T. distichum seedlings had not transitioned (i.e., saplings and young trees were absent) although no old-growth trees had died during or after the 1990s. In other regional swamps, projection models were constructed over two decades (2006–2021) along a dry-to-wet flood gradient including Section 8 Woods, Deer Pond, Wildcat Bluff, Snake Hole, and Heron Pond. Populations in swamps on the drier end of the gradient had more support from juvenile stages. In a tree health survey in 2022 within the impounded interior of Buttonland Swamp (not Crawford Tract), seventy percent of the old-growth T. distichum trees were stressed or declining. Coupled with the fact that no seedlings or saplings were observed, the populations in the interior of the swamp were not stable. Many factors could further stress these ancient T. distichum including interactions of impoundment with chemicals, disease, and changes in air temperature and precipitation. Overall, the seedling abundance in these swamps increased in these environments from 2012 to 2021, except in the most flooded swamps. From a management perspective, drier conditions were more conducive to the success of the earlier life history stages of T. distichum in these old-growth forests.