I have just rolled up a new rogue PC. The short version of my backstory is that I was betrayed by a member of my thieves' guild. The betrayal left most of my guild dead, me homeless, and all our treasure stolen. The betrayer has now joined another guild and knows that I still live. I joined the player party for allies and help in my revenge.

I want his payback to be public, humiliating and deadly. My character is based largely on Locke Lamora if you've read the books. He's a swashbuckler, a charlatan (con artist), and a face/master of disguise. I'm trying to come up with a scheme to have him arrested, tortured and executed publicly. But, I want him to know that I am the architect to his demise and I could care less about my lost treasure. I'm thinking that I might frame him for a theft from the local ruler, or build up a legend about him and tear him down. But that's as far as I got. Does anyone have any ideas on a complicated and confusing plot to achieve this goal? I don't know when the DM will open up the opportunity to confront him, but I want to be placing pieces for the plan from early levels. Basically, I would like to place a piece every time I return to town to build to his inevitable downfall.

Starting with Expertise in Persuasion and Deception at level 1. 

 What other interesting story hooks have you used for a rogue/swashbuckler?  I really don't want to play the sneaky rogue. 

How would you not be a “sneaky” rogue with expertise in deception building an intricate and elaborate frame job on an enemy across a period of months if not years?

Not a stab you from the shadows assassin style rogue? A thief but not a kleptomaniac rogue?  Only stealing from those who can afford it.  

Basically, I'm not going to be "stealthing" around everywhere.  I'm a con artist, not a cutpurse. 

Fair enough, though to be honest outside of an evil campaign I don't think most people play a cutpurse. I have a rogue/ranger I am playing in my campaign, my back story is that I was part of a hunters guild, the Redscar Jackals, my character specialized in the urban aspects. Someone who has an ear to the ground in every city, He is also a cartographer, mapping out cities to know where bandits would set up or flee to, in the the wild knowing how the landscape influences wild creatures habits so as to better hunt them.

Set up a "juicy" caravan ripe for the plunder with some plan in place to track where the goods go.  Find their safehouse but don't act yet.  Continue tracking the items to whomever they are sold to and begin to blackmail the purchasers with the information that they are 'knowingly' purchasing stolen goods.  Perhaps even make contact with them prior to the blackmail attempts to get an in with them.  Get the blackmailed parties to all put out interest in purchasing a specific item or goods from a certain area.  Proceed to make certain that none of the goods ever make it to the guild.  Sink ships, hire highwaymen to take out the caravans whatever it takes.  Then bring the now stolen goods and make an offer to the guild to sell them the goods they are looking for at a relatively exorbitant rate.  At this point the black mailed parties should be putting pressure on the guild to produce the goods they paid for or else.

Sell the goods in an area you know will end up in the safehouse you located previously (or safe houses if they are in multiple locales).  Make the negotiation extremely difficult on the guild to get the best deal possible and distract them from anything else going on.  When they make contact with the blackmailed parties that they finally have the goods promised steal the goods enroute to the deal location.  While this part is going on make sure to give trustworthy authorities all the known locations of the guilds activities and turn the whole thing into a huge sting operation.  Make sure they hit every spot known and if possible take their money, hit them where it hurts.  Have the black mailed parties demand the goods they were promised or else they will use their positions to wreck the guilds dealings, reputation is a big thing in those circles.  Make them demand that the guild leader deliver it personally.

Now agree to procure more of the goods and this time triple the price from the previous sale.  Maybe more.  This may get the leader involved personally to protect his interests.  With the leader in the open he may supervise the delivery of the goods to make the nobles happy and regain their goodwill.  At this point it is up to you to figure out some way to take him, either kidnap or publicly have them incarcerated.  If you go for capture make sure you have lots of ways to prevent magical escape, leaving one avenue open for escape, to the astral plane.  Wait for them there with an Iron Flask and trap him in it.  Keep him trapped in it as your prize.  If he isn't much for otherplanar jaunts Iron Bands of Bilarro is your go to, then drag him to the astral plane and flask him.  Putting a hex on him to give him disadvatage could be a wise choice as well to be certain of success.

I mean realistically talk to your DM about your plans and see how receptive to them he is.  Could make for a hell of a story line.

I would if i were in your shoes, dress up as that guy and commit crimes in a name you both know is you but everyone thinks could be him. As adventures you commit crimes all the time see murder hobos. Just when ever you commit a major crime dress up as that guy to do it.

It's not like he can tell anyone who you really are, or were to him. His current guild would likely kill him if they found out he murdered his last guild. Guards are not to fond of the whole i was in a thieves guild story either. 

Oh take trophies from some of the crimes and plant them at his home or hideout. This makes your frame believable and puts him on the outs with his current guild, for not sharing the loot or doing jobs on the side. Maybe tip them off too. 

I went for a suitably convoluted plan, can't let them see it coming.

Just be sure to embrace the consequences when the plan fails catastrophically.

that could be half the fun.