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Lost Character Study: Ben Versus Widmore Seemed Like A Brilliant Matchup

17 min readJun 12, 2025

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It Ended Up Being The Biggest Anticlimax of Lost

Each time I rewatch Lost I keep thinking that the final season and the controversial series finale are more and more fitting and perfect and lead to a fitting conclusion for one of the greatest of series of all time. That doesn’t make me any less aware of its flaws.

And if you had to ask me in hindsight what the biggest weakness of the final season is I wouldn’t need a second because it was clear to me while the final season was going on. And that was the final resolution of the battle between Ben Linus and Charles Widmore.

What bothers me most about it more than so many of the other loose ends during the series is that unlike the ones that were starting in the first half of the series and ended up being discarded by the second half up until the final season the writers had done such a magnificent job with every part of the storyline involving Charles Widmore. None of this is the fault of Alan Dale, who was exceptional in the first four seasons as a semi-regular as Charles Widmore. Rather the blame has to be put at the feet of Darlton. And to explain why I have to explain why from his first appearance at the end of Season 2 until the end of Season 5 Widmore seemed so important to the overarching story.

As any fan knows for his first three appearances the only reason Charles Widmore seemed significant was because he was the impediment between Desmond and Penny’s love story. That in itself would have been more than enough because all three episodes are ranked among the greatest in the show’s history.

When we first meet Widmore it is in the first flashback of Desmond Hume in ‘Live Together, Die Alone” He’s just been released from a military prison (we never learn the circumstances) and outside is Widmore in a limousine. Desmond is not happy to see him.

Widmore says he has two packages for Desmond: “One contains your past, the other your future.” The first package contains every single bit of correspondence between Desmond and Penny while Desmond was in prison. Widmore has gone to great lengths to intercept them all, which shows the lengths of both his power and is absolutely intention to keep the two apart. The other package contains a fortune for Desmond if he agrees to never see Penny again. “And why would I do it?” Desmond asks. “Because you’re a coward.”

Desmond then is determined to win Widmore’s race around the world to prove himself in the eyes of Widmore, who he considers the obstacle between him and a life with Penny. Later in that episode we meet Penny for the first time and it’s clear that despite what she says she would gladly run away with Desmond right then. When she asks him why he has to win this race he shouts: “I have to get my honor back.” That race leads him being shipwrecked, stranded in the Swan for three years pushing ‘the button’, and in a sense everything that we’ve seen on the island over the past two seasons.

The next time we see Widmore occurs in the classic ‘Flashes Before Your Eyes’. To this day it’s not clear what exactly happened to Desmond in this episode and how much of this happened the first time. However, since it’s not until after Desmond leaves Widmore’s office that he truly believes something strange is going on, I think it’s canon no matter what timeline it is.

This whiskey is too good for Desmond.

Any true fan of Lost has this scene committed to memory. Desmond has come to Widmore asking for Penny’s hand in marriage. Widmore says this is a generous gesture. He goes to a bottle of scotch called McCutcheon and tells the story of the man its named for. (It’s a fictional brand, so don’t look for it in your liquor store.) He then pours a drop into a single glass and says:

“This swallow is worth more than you could make in a month. (After he drinks it) To share it with you would be a waste, and a disgrace to the great man who made it. Because you, Hume, will never be a great man’.

This is one of the most brutal moments in a series full of them and Widmore doubles down on it: “What you are, Hume, is unworthy of drinking my whiskey. What makes you think you would ever be worthy of marrying my daughter?”

The thing is that it’s clear from everything Penny says and does around Desmond in this episode is that she loves Desmond and doesn’t give a damn about what her father thinks. (In one of the subtler allusions to the gulf between them though Alan Dale and Sonya Walger are frequently in the same episode, Charles and Penny never appear in the same scene whether in the present, flashback or flash sideways.) Desmond is the one who sees Widmore’s opinion of him as central to their happiness together. It is that reasoning that leads to Desmond’s decision to break it off with Penny and she knows the reason why: “You’re a coward.”

It was a given that Widmore was going to make an appearance in ‘The Constant’ at some point but the where is surprising. Desmond manages to find Widmore in an auction house where he is among those bidding on the journals of a former sailor who was once among the crew of the Black Rock. When the auctioneer tells the story as to when it disappeared, the fan of Lost takes note because we know where it ended up — in the middle of the island. So after Desmond pulls Widmore away and asks for Penny’s address the viewer’s less interested as to what Widmore will say as to why he was after the Black Rock. (Okay, yes we’re also waiting to see if Desmond will reconnect with Penny and whether or not this will cause him to be get on the right timeline. And then we spent the next several hours trying to recover from that final conversation. But the next day that was one of our big questions.)

Now as we recall Desmond became unstuck in time when he and Sayid were flying to the freighter which he knew very well was ‘NOT PENNY’S BOAT’. (Sorry couldn’t help it.) What’s interesting is that at this point in Season 4 no one had even asked the obvious question who’s boat it actually was? Ben had told us that the people on it represented a threat to the island and that they had come to get him. But none of the Freighter Folk had been forthcoming as to who actually sent them, even when Desmond asked Frank and Dan directly. Nikki Stafford had actually theorized it might have Charles Widmore who sent the boat in Season Three of Finding Lost and it’s now clear the writers had been hinting at in subtle ways throughout the early episodes. Widmore’s interest in the journals of the Black Rock was a big clue and a bigger one was the fact that they had received orders to jam all signals coming from a Penelope Widmore to the island.

So when Ben revealed in ‘The Other Woman’ that Charles Widmore had sent the boat and was looking for the island, it wasn’t a huge revelation. What was notable, however, was that when Locke asked how Widmore knew about the island and why he wanted it Ben chose to deflect. He gave some information about Widmore to Locke, which he said was the sum of his research. But by this point the viewer knew better than to take anything Ben said at face value so we knew there was more to the story.

And brother, did we get a lot of it in The Shape of Things to Come. (I’ll center on the flashforwards for the purposes of this episode.) We saw Ben recruit Sayid at Nadia’s funeral, luring him into be his personal hitman. We quickly realized that this was revenge for Keamy killing Alex in front of him (which we would later learn was just a few days after it happened) By that reasoning we realized Ben was about to use Sayid to kill people in Widmore’s organization. But none of that prepared us for the final flashforward, one of the highpoints of Season 4 and the entire series.

“Wake up, Charles.”

Ben has traveled to London and is making his way into the home of Charles Widmore. Oddly Widmore seems to be expecting him before Ben says: “Wake up Charles.” Widmore gets up and pours a glass of Scotch. Ben asks when he started doing that. “When the nightmares started,” Widmore says. He asks Ben, almost matter-of-factly if he’s here to kill him. “We both know I can’t do that,” Ben says just as calmly. None of these details are ever explained but they’re still chilling.

Ben says Widmore murdered his daughter. Widmore replies that they both know he did nothing of the sort and that Ben was the one who killed ‘that poor girl’. This tone is dismissive of a woman we (and Ben) have just seen killed in cold blood; we’ll later learn it’s practically a term of endearment from Widmore. Ben says: “it isn’t true I killed, Alex.” “Yes, Benjamin, it is,” Widmore replies. (As the series progresses we will see Ben come around to this way of thinking.) Widmore asks how does Ben think he’s the victim. “I know who you are, boy. What you are. I know everything you have you took from me. Now why are you here?”

Ben says: “I’m going to kill your daughter. Penelope was it. And once she’s dead, you’ll know how I feel and you’ll be sorry you changed the rules.” Widmore reacts just the slightest: “You’ll never find her.” Ben is about to leave. “That island is mine, Benjamin. It was once and it will be again.” “You’ll never find it,” Ben says. “Then I guess the hunt is on for the both of us,” Widmore replies calmly.

In Finding Lost Nikki Stafford points out the way the directors have lit the scene. “Ben is dressed all in black, with one side of his face completely swallowed up by the darkness and the other side lit up in blue. Widmore is wearing white, with one half of his face bathed in light and the other half in shadows. Both men take on a Janus-like appearance.” And as Stafford points out multiple times, black and white are major themes throughout Lost from the pilot.”

That said, I’m not sure I ever held with the argument that Stafford tried to make about whether watching this scene we could consider one character ‘good’ and one character ‘evil’, nor even be willing to consider either in the gray area of so many of the major characters we’d already met (and we still had a few to go). By this point the viewer knew Ben was responsible for truly horrible things and the horrors on the freighter came at Widmore’s bidding. By the time season 4 ended I thought trying to trust either man was like figuring out with snake was less poisonous and if the island was ever in the hands of either one, well, to quote Pierre Chang “God help us all.”

One of the reasons Season 5 is considered the best in the entire series overall is because the island blooping through time gives the full history of Widmore and Ben on the island. When we meet Widmore at seventeen, he is a headstrong, murderous young man capable of snapping a man’s neck if he tells someone too much. He later tells Locke that he was the leader of the Others before Ben displaced him and that much is true. In the classic episode ‘Dead is Dead’, we basically learn everything we need to know about who Widmore was — and how at some level, he hasn’t really changed since he was a boy.

When he’s forty we see him react angrily to Richard’s decision to heal Ben Linus, only backing off when Richard says: “Jacob wanted it done.” There’s no clear indication that Richard did this of anything other than his own initiative but the name is enough to get Charles to back off. Ten years later he sends a roughly twenty five year old Ben on a mission to kill Rousseau but he chooses to kidnap her infant daughter and leave her alone. This is the most forgivable thing we’ve seen Ben do. Widmore is outraged when Ben shows up ordering him to ‘kill it’. Ben challenges Widmore, asking if Jacob wanted this done and if that’s the case “then you do it” Again Jacob’s mere mention is enough to cause Widmore to back down.

Ben is sent on a mission by Widmore.

A decade later (the timetable for the flashbacks is difficult) Ben sends Widmore into exile for ‘breaking the rules’ — most notably having a daughter with an outsider. (We never learn who Penny’s mother was.) Widmore is arrogant but logical. He knows Ben has come to gloat. He points out that Ben broke the rules when he spared Alex. “You wanted that done, not Jacob,” he says. Widmore doesn’t buy it saying that one day he’ll be in this position “and then you’ll realize Benjamin, you cannot fight the inevitable.”

There was speculation at the time that Widmore was responsible for Oceanic 815 crashing. That I never bought but it was clear Widmore had spent all his time in exile trying to find the island. It’s likely the race around the world was staged as one attempt (which Desmond fell victim to) and Widmore clearly knew the plane crash happened because of the island, so he staged a false crash, complete with 324 dead bodies and sent a freighter to find the island. After that, he put a camera out in Tunisia (‘the exit’ as he told Locke) and when Locke emerged he persuaded him to help get the Oceanic 6 to return to the island. Locke should have known better — the only reason he was here was because Widmore had sent the freighter in the first place — but Widmore used the magic words “you’re special’ and Locke signed on to his mission.

Ben found out Locke had come back and clearly knew he was his key to go back to the island (see my previous entry) By that time he’d used Sayid as his hitman to take out Widmore’s organization. He’d manipulated Sayid by saying that Widmore was a threat to his friends but by the time we learned how Sayid came back to the island (“He’s Our You”) it was no longer clear if Widmore was a genuine threat or Ben was exercising revenge on his old enemy for the death of Alex. Considering that he tried to manipulate Sayid by saying that Widmore’s people had killed Locke (when we’d seen him do it) there’s a good chance the only danger the Oceanic 6 were from all this time may have been Ben.

It was clear in the lead up to the Ajira flight that Ben was willing to do anything to get the Oceanics back on a plane together. He manipulated Jack (who didn’t need much convincing). He tried to persuade Kate that people knew Aaron wasn’t her biological son in order to get her to run. When Hurley tried to get away from him by confessing to murder, he used his attorney to get him out of jail. When Sun put a gun to his head blaming him for killing Jin, he told her Jin was alive and gave her Jin’s wedding ring. Of course, he’d taken it from Locke after he had promised Jin that he wouldn’t bring Sun back to the island.

So when Ben calls Widmore and tells him that he’s heading back to the island and that before he does he’s going to keep his promise, it seems to be the fitting end to their decades long war. Instead, it’s the beginning of the end for the control Ben has had of events since he left the island. He puts a bullet in Desmond, walks up to Penny, and then for the first time in two years, hesitates. Charlie Hume appears and the parallel between when he was sent to kill Rousseau but couldn’t is made clear. He finds himself having to explain himself and you can tell, hearing himself say it, how weak his excuses are. And that hesitation is long enough for Desmond to recover, beat the snot out of him and throw him in the marina. Ben is forced to call Jack in agony, get himself stitched up and only makes it on Ajira 316 in the nick of time. As I mentioned in my entry on Locke and Ben, whatever hopes he has for reclaiming his position die when he wakes to see ‘Locke’ telling him: “Welcome back to the land of the living.’ Combined with the sequences that take place in civilization in ‘The Variable’, with Widmore standing outside the hospital, unable to talk with his daughter, it almost seems like the writers were wrapping up the Ben and Widmore storyline right then.

The real problem with Widmore is the fact that once Jacob and the Man In Black’s endgame takes center stage during the final season, the struggles between Ben and Widmore seem insignificant by comparison. By the time of Dr. Linus, it’s clear that what’s important is the remaining candidates, and how they fit in the game between these two adversaries. So when Widmore shows up at the end of the episode we’re brought up short.

I do think this is where the writers truly dropped the ball in the final season. It’s not entirely on them; having spent so much of the last two seasons making the struggle between Widmore and Ben seem significant to the show’s endgame; they might have felt an obligation to wrap it up in the final episodes. But while Ben’s arc in the final season is magnificently handled from beginning to end, Widmore’s feels tacked on and makes us question why the viewer ever thought he was a threat in the first place.

First there’s the fact that while it seems to have taken him somewhere between ten and twenty years to find the island back in Season 3 — and their seemed no indication that he had any idea where it was in Season 5 — he just shows up in a submarine with none of the struggles the freighter did three seasons earlier. We saw that just coming close to the island in Season 4 caused almost everybody onboard the freighter to slowly go insane or kill themselves but the submarine gets there with no problems for Widmore or the passengers.

Second there’s the problem of Widmore’s ability to choose the best people. When he was staffing the freighter it was very clear that everyone on it was given a certain amount of information and each was given a different objective. Naomi seemed to know about the mission but not whether there were survivors; all four members of the science team seemed to know certain amounts of the mission but not all of it and Captain Gault and Keamy’s mercenaries were given two different protocols. It’s not the main reason almost everybody who was part of the mission died but it’s close.

Once the Oceanic 6 come back, Widmore’s operatives are killed off one by one by Sayid and somehow seem to be unaware of the threat right up until he kills the last one. Widmore knows Ben is off the island and he has to know someone is killing people who work for it but he never informs any of them.

Widmore with the leader of the crack team he went to the island with.

And now on what is supposed to be the most important mission he’s ever been handing he hires a team of scientists who are just as incompetent at following orders and less informed what the mission is. It’s hardly surprising the Smoke Monster manages to kill almost all of them off, but they’re so incompetent that you almost think that they’d just as easily blow their own heads off handling guns.

Third, in the penultimate episode of the show Widmore tells us he came to the island after a meeting with Jacob, who convinced him of the error of his ways and told him what he needed to do save the island. To be fair, the writers don’t officially confirm that this is canon but even if it is why would Jacob come to Widmore after never coming to him when he was leader of the Others? Why would he come to him after Widmore sent a team that caused so much bloodshed and death — and no doubt killed off quite a few of the Candidates? And even in the context of the season Widmore clearly hasn’t been told everything he needs to know about the Smoke Monster or why he needs to protect the remaining candidates, neither of which he had any real awareness of when he spent all that time on the island in the first place.

Lastly, there’s almost no evidence in the final season that Widmore has learned the error of his ways. When Sawyer comes to see him on the submarine and reminds him of the role he played in sending the freighter, Widmore not only doesn’t take responsibility he puts the burden back on Ben. And when his final confrontation with Ben occurs in the penultimate episode, he seems more interesting in lording his presence over Ben that working together to save the island. When he’s finally confronted by the Smoke Monster, he folds like a cheap suit and tells him everything he needs to know before Ben kills him.

And to that point, Widmore’s presence does much to tarnish the redemption arc that the show has been working for Ben during the final season. Ever since he returned to the island he has taken responsibility for Alex’s death, finally realized he has been nothing more than a pawn for the wrong side all this time, and that everything he’s done has been a cosmic joke. Watching Emerson in this final season shows some of his best work yet: for three and a half years we’ve been led to believe he is the villain of Lost. But as the last season and a half unfold, we learn he’s never really had any power, has always been a pawn as much as anyone else and is manipulated to kill Jacob. He spends most of the season being led around docilely, making remarks with a dead tone, and even his sarcasm is muted.

When Widmore shows up on his doorstep Ben revives and stands outside his old house, waiting for ‘Locke’ to show up. He barely blinks when Richard is cast aside by the pillar of smoke. He doesn’t seem to care anymore about dying and almost seems willing to believe the Man in Black, if it means Widmore gets what he deserves. And even his killing of Widmore lacks the satisfaction it should because of the premise that Ben couldn’t kill Widmore when they met in Shape of Things to Come because of ‘the rules’. It really makes you think their battle over the last season was just mindless bloodletting.

I find it notable that in the series finale Ben is allowed redemption both on the island and in the flash-sideways but there’s no presence of Widmore at all in the latter, even though Eloise Hawking (his wife in this world) has a critical role and both of his children have critical parts. Desmond has a confrontation with Eloise that brings closure but none with the other man who made his life so miserable.

Why don’t we see Widmore in the series finale, even to know if he’s stuck in the same limbo as his wife or Ben? Honestly, I think its because Darlton realized that it didn’t matter anymore. The island was done with Widmore and honestly, after Season 5, they should have been to.

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David B Morris
David B Morris

Written by David B Morris

After years of laboring for love in my blog on TV, I have decided to expand my horizons by blogging about my great love to a new and hopefully wider field.

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