- "Let them taste the triple guns."
- ―Davy Jones and Ogilvey
At an unknown point in his life, he became a part of the Crew of the Flying Dutchman under Davy Jones. The crew of the Dutchman gradually took on characteristics of sea creatures over time, slowly taking away their humanity. Ogilvey was likely one of the crew members to have been serving under Jones the longest at the time of the mad search for the Dead Man's Chest as his transformation was particularly startling; his face had lost all humanity. A single red eye peered out from a grimy, coral-like countenance dominated by a twisted mouth. He spoke with a gravelly tone, and commonly wore a bandana. He fought with a hook and carried a sword. Overall, Ogilvey was a tall man, with a chubby belly and was, like Maccus and Crash, counted among other long-time members of Jones's crew as being among the fiercest and most efficient, which eventually earned him the accolade of head gunner aboard the Dutchman. Perhaps ironically even Ogilvey could not compete with the outlandish transformations of some of the Dutchman's even older and more haggard members like Hadras, whose head actually became an entire conch shell, or Wyvern who had actually started to meld to the ship itself. He was one of the crew members who attacked Will Turner during Jack Sparrow's attempt to settle his debt with Davy Jones. After Clanker, Ogilvey attacked Will, who proceeded to set fire to his sword. He sliced open Ogilvey's gut with the flaming sword, spilling fish and chum onto the deck. Later, he would stitch it up with a fishhook. While Will was distracted by watching Ogilvey scream and fall over, Crash knocked Will unconscious using his pulley. After Jones arrived and persuaded some of the surviving men of the ship to join his crew, he was indirectly notified by Turner that Sparrow was attempting to weasel his way out of his debt, whereupon Jones, with Ogilvey and the rest of the Dutchman crew in tow, immediately teleported to the nearby Black Pearl. While Jones confronted Sparrow over his debt Ogilvey and the rest of the Dutchman crew held back the Motley crew with Ogilvey and Crash taking Joshamee Gibbs prisoner.
Later, as several crewmen were working around the ship, Ogilvey was among them. He watched as Davy Jones had William "Bootstrap Bill" Turner Sr punish his son. He watched as Maccus, Koleniko, and Clanker played Liar's Dice, and then looked on as William Turner challenged and played against Davy Jones. He executed a crewman of the Edinburgh Trader after the ship was ripped apart by the Kraken.
As the crew travelled to Isla Cruces in Jones' stead, Ogilvey remained aboard the Dutchman. Later when the Dutchman ambushed the Pearl off Isla Cruces, Ogilvey was ordered to 'let them taste the triple guns' by Jones, and relayed this order with obedience. The Pearl got away, but was soon tracked down and destroyed by the Kraken. Ogilvey witnessed Jones' rage when he opened the chest and discovered his heart was not there.
He was present as the East India Trading Company crew of the HMS Endeavour under Lord Cutler Beckett boarded the Flying Dutchman. Jones pushed past him to talk to Beckett. The East India Company soon took over the ship. By order of Beckett and Jones, he and the crew attacked Sao Feng's flagship, the Empress, and executed most of the crew. Ogilvey was shocked to later find Admiral James Norrington dead at the hands of Bootstrap Bill Turner and Davy Jones. He fled to the captain's cabin at Maccus' command. He fought in the battle around Calypso's maelstrom and survived to be reverted back to human form.
Behind the scenes
- Pirates of the Caribbean: Dead Man's Chest (First appearance)
- Pirates of the Caribbean: At World's End