This study explores the inverse relationship between sea level pressure and tropical cyclones in the tropical Atlantic (TA). Upper-air observations, the National Centers for Environmental Prediction (formerly the National Meteorological Center)/National Center for Atmospheric Research (NCEP/NCAR) reanalysis, and regional SSTs provide clues as to the physics of this relationship using composite and regression methods. Stratification of upper-air data by sea level pressure anomalies in the TA yields several interesting results, including anomalously high (low) pressure association with relatively dry (moist) middle levels, cooler (warmer) midlevel temperatures, and stronger (weaker) 200–850-mb vertical wind shears. The configuration of these composite wind differences suggests that higher summertime pressure in the TA is associated with an anomalously strong tropical upper tropospheric trough (TUTT) circulation. The observations show systematic association between the composite moisture, temperature, and wind differences. Studies of longwave sensitivity using a two stream model show that the moisture field dominates the longwave radiative cooling; hence, dry midlevels enhance cooling of the atmosphere. The effects of SST variations and tropical cyclones on TA pressure anomalies suggest that summertime pressure in this region is strongly influenced by additional (unresolved) climate forcings. These findings lead to a hypothesis that explains both the persistent nature of the summertime pressure (in the TA) as well as how variations of this pressure modulate the TUTT circulation strength. The hypothesis states that positive feedbacks operate between pressure/subsidence variations, midlevel moisture, and differential longwave radiative cooling that affects local baroclinicity (i.e., TUTT). When pressures are anomalously high, subsidence is greater and middle levels are dryer, resulting in increased atmospheric cooling to space and increased baroclinicity. Hence, pressure-related variations of both the midlevel moisture field and the TUTT circulation result in modulations of the upper-level winds and vertical wind shears in the TA. These, in turn, are found to be the primary cause of the observed pressure–tropical cyclone relationship; higher tropical Atlantic pressure results in an environment that is dryer and more sheared and, thus, less favorable for tropical cyclone formation and development.