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Sometime in the 2350s, Whaldron met Steve Tecklenberg under "extraordinary circumstances." Tecklenberg recommended him for the Starfleet, but rather than attending Starfleet Academy, Whaldron enlisted in 2360. (Star Trek: Pendragon: "Still Comes the Dawn")
Two years later, he joined the Starfleet SEALs and was assigned to SEAL Team Zeta-2, where he served with distinction for many years. Following the Federation Civil War, Whaldron was promoted to Master Chief Petty Officer. (PDN: "To Follow a Sinking Star")
In 2375, he was part of a team assigned to bring down a cell of the Destiny's Hand terrorist group operating on Kaldora V. During a skirmish, the team was pinned down near the colony's fusion core. Whaldron threw himself on a photon grenade to shield his teammates and prevent catastrophic damage to the reactor. His Brikar physiology enabled him to survive the blast, but his epistrata and dermastrata were ruptured beyond his natural ability to heal completely. (PDN: "Red Sky")
Though he was awarded the Bronze Star, Whaldron was no longer fit for active SEAL duty and transferred to the Starfleet Corps of Engineers, with a field commission of Lieutenant junior grade. He was a full Lieutenant when he was posted to the USS Pendragon, replacing the deceased Lieutenant Svek as Chief Engineer. (PDN: "Still Comes the Dawn")