“The Undertaking” is episode twenty-one of season one of Arrow.
The episode opens with a man counting money and placing it in a briefcase as two goons watch. The man uses the intercom to tell someone to call Cayman Fidelity and say that their favourite accountant is flying in for a special deposit from a special customer. Then all three hear the lift. The man with the money says that the elevator is supposed to be on a key, and tells the two bodyguards to check it out. When the lift doors open it is, of course, empty. Then Oliver drops down out of the ceiling behind the two and quickly takes them down. Oliver approaches the third man, calling him Harold Backman and telling him he has failed the city by taking money from extortion, kidnapping and drugs and causing the destruction of innocent lives – although Backman claims he is just the accountant. Backman asks Oliver if he thinks he scares him more than the people Backman works for. Oliver tells him no, takes Backman’s laptop and leaves, telling Backman that he will let the people he works for deal with him.
Oliver drops the laptop in front of Felicity. She asks why not simply turn it over to the IRS; Oliver says that he will – once the money has been returned to its rightful owners. Felicity tells Oliver the laptop is heavily encrypted and Oliver interprets what she tells him as it will take some time to break in. Days, Felicity replies, so Oliver tells her she had better get started. First, Felicity brings up the topic of Diggle. In the previous episode, “Home Invasion”, Oliver hadn’t turned up to kill Deadshot like he promised Digg, instead dealing with Edward Rasmus. Several A.R.G.U.S. agents died – because Diggle’s presence at the sting had tipped Deadshot off – and Digg walked out on Oliver. Felicity asks if Oliver is going to make peace with Digg. He responds that he did everything he could to stop Digg leaving. Except apologise is Felicity’s response. Oliver says he made a choice he can live with.
Moira is on the phone with someone. She is telling them that it is only six months and that she is very aware of the stats but she hasn’t given up hope and neither should they. Afterwards, Thea asks what it was about. The insurance company is insisting on paying out Walter’s life insurance. Thea says that she misses him too, and it’s like losing her father all over again.
This gives Moira a flashback. She answers the door to Malcolm Merlyn, and they discuss Oliver and Tommy. Moira shows Malcolm into a room where Richard and several other men are waiting. The door goes again and it’s Walter. He apologises for bothering Moira at home; he has some papers for Richard to sign related to the stock offering. Moira tells Walter that Richard is in a private meeting but he can wait in the study. Or Walter can help get Moira’s children out of the house. She asks Walter if he has children and he replies he hasn’t yet. Moira tells Walter not to bother – eventually they all turn into teenagers.
The topic at Richard’s meeting is currently Adam Hunt. Proof of his embezzlement has persuaded Hunt to make an anonymous donation. The others are happy but Malcolm says it’s like emptying the Atlantic with a tablespoon. For years they have been persuading Starling City’s worst to do their best by leveraging them to help save the city. But it isn’t working. Malcolm tosses a book containing the list down on the table. He continues, saying that crime in the Glades is rising and the cancer is spreading. Everyone in this room has lost someone or something to the Glades.
They may be committed to fixing the Glades but Malcolm tells them they have accomplished nothing. The Glades cannot be fixed. So Malcolm wants to abandon what they are doing in favour of a new undertaking. Malcolm wants to level the Glades down to the bedrock and make Starling City safe for everyone again. When it’s stated that suspicion would fall on them, Malcolm says it wouldn’t – not if it was a natural disaster. Robert tells Malcolm that his god complex is part of his charm, but even he cannot create a natural disaster. Malcolm brings up a company, Unidek Industries. They have an idea, according to Malcolm, that will serve their purposes, but they are five years away from a prototype. Malcolm says that they just need patience; Robert replies that they also need restraint. Malcolm tells him that one man alone can’t save the city; they both know that.
Laurel is drinking coffee in Oliver’s club. She tells him it’s terrible and he replies that’s what you get for ordering coffee in a bar. Laurel is tired, and she explains that it’s from too much crying. That Tommy broke up with her and she has no idea why. She asks Oliver if he knows but he sort of avoids the subject and replies that he and Tommy haven’t talked very much since he quit. Oliver thinks that Tommy will come around. Laurel says that maybe he has got cold feet – just like Oliver did. As why else would you go off with your girlfriend’s sister. Oliver tells Laurel that if she still wants to be with Tommy, she should do what he and Laurel should have done. Talked to each other. Honestly. At which point Felicity turns up babbling and says she totally walked in on a thing. Their story is that Felicity is dealing with Oliver’s internet – router – and she needs to show him something important.
Felicity hasn’t broken the laptop’s encryption totally; she hacked the bank and got a list of deposits. Oliver wants to know what good that is if they don’t know who the money belongs to. Felicity wants Oliver to look at a specific deposit from last year. One of Backman’s clients was paid $2 million on December 12th. The day Walter disappeared in “Year’s End”. If they can find the client, they can use them to find Walter. Felicity asks if Oliver thinks Walter is still alive. He honestly doesn’t know.
The person who got paid the money is a Dominic Alonzo. Oliver knows the name; Alonzo runs the biggest underground casino in Starling City. When he isn’t kidnapping people. Felicity asks Oliver how many arrows it will take to get Alonzo to divulge Walter’s location. Oliver doesn’t think it will be that easy, as the casino has its own private army. They need to find a way to access his computer without setting off alarms. Felicity replies that they need all the help they can get. Too bad there isn’t someone else they can call. Not very subtle.
Felicity, with the Diggle option rejected, continues, saying that it looks like someone’s going gambling. Oliver replies that Oliver Queen would never be caught dead in a place like that. Felicity wasn’t talking about Oliver going. Oliver does not like this idea. Felicity tells him she can count cards and knows her way around a casino. The reason she joined Oliver in the first place was to find Walter. Oliver agrees to let her do it, but his way.
First Felicity goes to see Digg. He does not greet her very politely and she pulls him up on this, asking if it’s any way to greet a girl who has just walked up six flights of stairs. Walter admits it isn’t and invites her in. Digg wants to know if Oliver sent her; he did not. Digg tells her that he and Oliver do not need a relationship counsellor. Felicity disagrees, based on her experience. She tells him about the lead on Walter and asks him to come back to help. She knows that Diggle is not happy with Oliver, and tells him that if it was Digg’s life on the line, he would be there. Felicity tells Digg that Oliver needs him; when Oliver is willing to say that to Diggle, he knows where he lives.
Felicity is heading to the casino and Oliver checks she is clear on the plan. Felicity tells him it’s to be caught counting cards in an underground casino filled with criminals. Put like that, this sounds like a terrible plan. This will result in Alonzo giving Felicity a friendly warning in his office, allowing her to bug his computer. Assuming Alonzo gives her a friendly warning and not a bullet. Oliver tells Felicity she doesn’t have to do this. She says she does.
Inside, Felicity gives Oliver a rundown on the men inside. And makes a comment about it feeling good to have Oliver inside her. Then realises what she said, tries to explain and eventually says she will stop talking. Which is Oliver’s preference. Felicity gets herself in then, when she wins big at blackjack, is asked to come with one of the heavies. She is take to Alonzo’s office and he asks if she is familiar with the term ‘Eighty-Six.‘ Felicity replies that she does and starts explaining (one of the possible origins) before saying she will stop talking. Alonzo tells her the term no means to ban someone for cheating. She is Eighty-Six’d. Take her chips and go.
As Felicity is heading out, the heavy waves a wand over her first. Alonzo tells Felicity that sometimes card counters work with a partner. He removes Felicity’s earwig and crushes it. Felicity tells Alonzo he will be really upset when he meets her partner. And Oliver breaks into the place and takes down all the thugs. So much for the private army Oliver was concerned about. Alonzo, when questioned, tells Oliver and Felicity that Walter is dead. He delivered Walter and heard a gunshot. Oliver passes this information, not giving the true source, to Thea and Moira, and Moira takes it in a way that is more than a little odd. Because of course she knew about the kidnapping. Which leads to Oliver making some unexpected discoveries.
Laurel’s honest talk with Tommy does not quite go the way she expected. Tommy tells her what the honest truth is. Laurel belongs with Oliver, because Oliver is still in love with her.
There are more clips from the past when Malcolm was discussing his new undertaking. After the meeting, Robert sees Malcolm is still there. Malcolm hadn’t left because he’s still waiting for an answer. The Glades are the place that took Robert’s soul. Robert says that what Malcolm is planning won’t bring it back, or Malcolm’s wife. Malcolm remembers the day his wife died. She had been trying to contact him and he ignored her, then turned his phone off. Then SCPD arrived on his doorstep and told him she had been murdered in the Glades. Malcolm listened to the messages she had left on his phone. She was asking for help. Dying. Malcolm listened to his wife die over and over again.
Malcolm has told Moira the device is finally ready and is being shipped to Starling City as they speak. Malcolm has sometimes wavered, but Moira’s endless support has given him the strength to carry on. They will always have a connection. And he is sorry he had to take Robert from her. Moira says that it was her fault. Back in the past, Robert told Moira about Malcolm’s plan. He admits that when he opened a factory in the Glades a local councilman tried to get Robert to bribe him. There was an argument; the man fell. This work is Robert’s penance. Moira does not feel that killing thousands will atone for one murder. She wants him to prevent the horror and make it right. So Robert speaks to David Chen, and plans to meet him in China. Robert will take the Queen’s Gambit. You can guess which voyage that was.