Regenerating longleaf pine (LP) (Pinus palustris Mill.) is essential for sustaining the production of high-value wood products and ecological benefits. Understanding the relationship between LP growth and cone production is critical for this effort, as both processes contribute to natural regeneration. In this study, we tracked the growth and cone production of individual LP trees at three sites across the natural range of LP over six-decades. Our results indicate that diameter growth increased linearly with time on a yearly scale before sampling, though the radius increments at tree bases varied from 0.5 mm to 8.0 mm each year. Basal area increment had no significant correlations with annual precipitation or average air temperature. Tree height growth generally slowed after 30~40 years. Cone production had no significant relationship with basal area increment, and their variance dynamics differed. During the cone monitoring period, the basal area increments of each tree followed power laws. A significant relationship existed between radii (basal areas or stem volumes) and the accumulated cone production. These results provide helpful information on the growth characteristics and functional tradeoff between growth and reproduction at individual trees.