Fans have pointed out a number of Lost plot holes over the years, but the unanswered outrigger chase scene is the show's worst. A decade on from its dramatic and divisive finale, Lost continues to intrigue and confound in equal measure, and while the series is still revered by many, there remain a smattering of unresolved mysteries and lingering questions. So many, in fact, that a short film was produced to try and plug some of the gaps. "The New Man In Charge" answered the Hurley bird mystery, the supply drops and, to an extent, why Walt was special, but it couldn't tie up every loose end.
What was the heart of the island? Who was Mother? Why were Libby and Hurley in the same institution? Many questions remain, but perhaps the worst plot hole Lost is guilty of concerns the season 5 outrigger chase scene. In "The Little Prince," those left behind on the island are experiencing time flashes as the island skips from one era to the next. Eventually, the group (Sawyer, Locke, Juliet, Miles, Daniel and Charlotte), find themselves in the future and head for the Orchid in an attempt to settle the island. They take an outrigger canoe from the shore in order to make the trip but are soon pursued by a mysterious group who have taken another boat and are now shooting at Sawyer's people. Juliet returns fire and manages to take one enemy out, but another time flash interrupts the fight.
This scene immediately posed a new question - who had deliberately chased after the survivors and tried to kill them? "The Little Prince" aired in the days before The Man in Black was revealed, so the identity of Lost's big bad and the show's overall endgame was still a mystery, and any new assailants emerging from the shadows felt like a potentially big clue. Had another group arrived on the island? Were there more of Jacob's followers coming out of the woodwork? Or was this a future enemy to be introduced in the following season? There were so many possibilities as to who the outrigger attackers could be, and the identities of the assailants was established as a significant plot point.
Unfortunately, this particular box went entirely unchecked throughout Lost's remaining episodes, with no light whatsoever shed on who the outrigger pursuers could be. Damon Lindelof has since confirmed that the intention was to revisit the outrigger mystery in season 6, but characters that had previous been penciled in as the attackers had died by then and Lost's final run of episodes didn't provide a natural opportunity for the question to be revisited. Various sources have confirmed that the original scripts did specify who the attackers were.
Additional material has since attempted to fill the blank, suggesting that occupants of the Black Rock from the past, who also might've been caught up in time flashes, were the ones engaging Sawyer's team. Whether this explanation is canon is debatable, and the answer also doesn't account for why Black Rock sailors would go out of their way to chase and assail another group.
The outrigger chase mystery is Lost's worst plot hole simply because it's the most unnecessary and the most irritating. Lindelof and Cuse can get away with not explaining the Mother and the nature of the island by playing the "answers only lead to more questions" wavy-hands, smoke and mirrors card, while unanswered points such as Libby being institutionalized have implicit answers, even if explicit ones would've been preferable. The outrigger chase falls into neither category, and is a classic example of introducing a mystery for mystery's sake, adding a bit of action and intrigue to an otherwise uneventful episode. Lost is often unfairly criticized for a lack of long-term planning, but introducing a mystery only to run out of time before solving it typifies why so many fans fell out of love with the series.