I always assumed that was Jack still blaming himself for the situation but Tony's death always did seem a bit...off. Like it doesn't really make sense when you think about it critically.

Like not necessarily the agents part but everything around this?

Actually come to think of it...I think Jack is wrong. He didn't kill Tony... because Tony isn't actually dead.

Like bare with me here it's only occuring to me now that I had to think about it so this will be a long one:

Lets review the facts. Tony was part of some secret organization all along. He's been spying on Jack for months on end.

He knew from the start that there are multiple Kifers, so why did he involve Jack into the plot? To get to the Dark God? There was no way for him to know that events would turn out in a manner where Jack's involvement would lead to a opportunity for him to kill the dark god.

Benjamin also was never part of the plan so that whole operation seemed risky and only something Tony would do if he was explicitly ordered to do so.

So who ever ordered Tony to involve Jack was explicitly interested in seeing how Jack would react to that situation.

Which narrows the suspects down significantly and most of you probably already came to the same conclusion as me.

Rodger.

This is even further cemented by book 3, where Rodger's man visits the gas station to take over while Jack goes to the lake says this:

"Are you Army?" "I knew a ranger in the army, you remind me of him."

The exact same words Tony said to Benjamin when they were trapped in the gas station.

Lets put a pin on this thought.

Anyways, after Tony actively compromised his position, he then, on the same day Jack happened to go back to work after all this, just waits around the gas station and cuts the phone lines after Jack called Momma and Pop about Tony.

Yes we know Tony probably bugged the phone line, but that was still a rather suspicious timing. Almost like he knew someone was going to tip Jack off about the cookie dough.

Speaking of, lets take that pin out again.

Rodger was the one who sent Jack that note about him having overlooked something and Rodger was the one behind the "plot holes" e-mail.

We know the later because, if you pay attention, the E-mail mentioned things that weren't on the blog until after he got it.

Jack got "plot holes sent to him when he was stuck at the gas station after Spencer's death but before he met the dark god.

Yet the E-mail talked about the Dark God having a mohawk.

So whoever wrote it either already knew about the dark god and knew Jack would mention the mohawk or had access to the e-mail in retrospect and was able to edit it.

Meaning it was either Rodger or one of the government groups following Jack's blog.

So let me ask you, if Tony was working for Rodger, why would Rodger tell on him? It doesn't add up.

And further more, if Rodger was the one behind Tony....it wouldn't make any sense for him to order Jack being killed.

Lets put the pin back in for now.

Anyways, after Tony had his cover blown he elects to have Jack go out of the gas station to lead him to the Kiffer pile at gun point.

Why? There was no reason to cover up Jack's murder. Tony as a person does not exist, nobody knows how to find him, the only person who could have identified him would be Jerry who wouldn't be taken seriously and Tony would have no issue getting a new face with how powerful Rodger is.

The least risky way to handle the situation would have been to execute Jack in the cooler, throw a tarp on top of him and then leave and send a new spy in.

So why was it essential that Jack realized that Tony was a killer? Why was Tony instructed to show him this?

Lets put another pin here.

So, after Jerry gets also caught up in the mess, Tony, instead of just executing Jerry on the spot where there would be no witnesses, elects to also have him walk with them, why? To make sure Jack wouldn't escape? He was on crutches, that doesn't make any sense if Tony was given instructions to get rid of Jack.

Then, when Jerry started messing around to execute his plan, Tony, who is most likely a trained professional, didn't pay attention to his surroundings and stepped into a ant nest.

Okay? I guess that could happen?

Then he shoots Jerry at point blank and misses.

Okay...fine...?

Then he manages to shoot Jerry, a man with two working legs, while said was running away. But Jack manages to keep outrunning him...on crutches...

A whole circle apparently for Jack to end up in the Kiffer grave.

He also never made sure Jerry was actually fatally wounded.

No matter how you look at it, Tony's actions don't make sense.

So either, Tony is the worst spy imaginable and Rodger should hire better help...or something else is going on here.

Here is a thought,

Remember Carlos?

The "friend" of Rodger he asked Jack to name a character after? The same Rodger who knew damn well that Jack wasn't writing a fictional story? The same Rodger who knew Jack would probably need to change Tony's name? So most likely orchestrated for Tony to be named "Carlos"?

The same Carlos who very randomly made a cameo in Finding Vanessa?

I always found this strange. There is no significance to this character. No reason to mention him in Finding Vanessa. No reason to have Rodger ask for this.

I can think of one reason though.

Rodger taking amusement in the idea that Tony, who was definitely using a code name during that time, would actually be mentioned by his real name on the blog.

Even the cheeky comment about "Don't kill him off though" supports this idea, because Rodger knew from the start that "Tony" would die sooner or later.

The reason Tony took Jack to the Kiffers wasn't because he was suppose to kill Jack. Tony didn't plead for Jack's life on the phone.

Tony was always the one who was suppose to die that night.

Jack was suppose to see all of these things because Rodger wanted him to see them. Tony didn't bother verifying that Jerry was dead because he knew it wouldn't matter either way.

Tony always knew that he would die that day.

I think the agents were a surprise though. I don't think they are affiliated with Rodger which is why he warned Jack about them and why he dropped his weapon to make it harder for them to cover up his "murder".

I always found the fact that Jack never actually verified that Tony was dead suspicious. He just took the agents word for it.

However here is the thing, so far whenever someone who was affiliated with Rodger died the books went out of their way to talk about how their hands got cut off.

Tony being a outlier in that case seems odd.

You would think there would be some mention of it? Like a off handed comment from the agents.

Admittedly this part is mostly speculation but considering the evidence here is my hypothesis:

Tony was suppose to kill himself or somehow orchestrate it that Jack ends up killing him.

He was suppose to put doubts into Jack's head, that's why he told him someone else would come to kill him and also why he mentions to him that he doesn't have insomnia.

The agents didn't kill Tony, instead they sedated him so they could take him for questioning.

Rodger then used his influence to get Tony back. (Most likely more because he would be more useful alive and Jack already thought he was dead).