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Overview:
-Estimated trophy difficulty: 4/10
-Overall number of trophies: 10
-Offline: 1
-Online: 8

1
-Approximate time to 100%: 4-6 hours, Longer if you have not Reached level 50 as of yet. 15+ Hours
Offline
AXE MASTER
Complete all Tomahawk challenges in Single Player.
This is just like an ambient challenge. It can be viewed in your Journal. Go into your Journal in the Start screen and then click on Challenges. There are 5 levels for the Tomahawk Challenge and you can start them by buying the Tomahawk from Manzanita Post.
1. Buy the Tomahawk from Manzanita Post. Each Tomahawk costs 10 dollars for 1 and 200 dollars for 20.
2. Kill one enemy with the Tomahawk used as a throwing weapon, one as a melee weapon and one from horseback. This doesn't have to be in any order.
Throwing Weapon: Take the Tomahawk out and throw it at anyone to complete this part of the challenge.
Melee Weapon: Stand right next someone to kill that person to complete this part of the challenge.
From Horseback: While on a horse throw the Tomahawk at someone to complete the challenge all together.
3. Kill a flying bird with a Tomahawk without using Deadeye.
Go to Hanging Rock, which is north of Armadillo. Go on top of any of the mountains in that area and wait for a bird to get close and then make your move, a few throws, but you will kill a bird sooner or later. It is easier to kill a flying bird during the daytime.
Note: After you have cleared a hideout you can just take out your Tomahawk and hit a vulture with it, if you learned their predictable flight pattern (Thanks to
mjc0961). Try the Twin Rocks gang hideout. There aren't too many enemies there, so just take 3 minutes to clean them out and bam: a flock of vultures start circling in the air. From there you just have climb to the roof of the house in the middle and then it will be easier to tomahawk one of the vultures because of their easy to predict flight pattern.
4. Kill 5 enemies in a row "without" missing with the Tomahawk.
Try this at Solomon's Folly. The enemies are out in the open and there is more cover. Restock on Tomahawks if you are low. Solomon's Folly has exactly 5 enemies to kill at the hideout so it should be no problem.
5. Complete a gang hideout using only the Tomahawk.
If you started Challenge 4 at Solomon's Folly and finished it, complete the hideout with only using the Tomahawk to finish Challenge 5. If you miss while trying to kill an enemy while driving the wagon it's okay,
JUST DON'T USE ANY OTHER WEAPON.
Due to the title update(1.04) you may have trouble earning this rank right after earning Rank 4 while completing Solomons Folly. You just have to complete Solomons Folly a second time for the trophy to pop up. Thanks
Frejim for info.
Online
ALL trophies can be earned in Private Mode/Match.
CALL IT A COMEBACK!
Come back from a 2-0 deficit and win a Hold Your Own game.
Use the
Trophy Boosting Thread.
You need at least two people including yourself to get this trophy. What you need to do is let the other player get your bag 2 times in their chest and after they get 2 bags and you are still at zero, you can go ahead and win it by getting three of their bags, after the match ends you will be rewarded with the trophy.
WHO NEEDS DEADEYE?
Kill 3 or more players in a standoff or showdown.
Use the
Trophy Boosting Thread.
You need at least four people including yourself to get this trophy. Start a match with at least 4 people, whether it be a Free For All or a gang match, and kill 3 people. While in the standoff kill 3 other members before the standoff ends.
STICK AND MOVE
Get 3 kills with knives or throwing knives in a single competitive match.
Using the standard melee knife will take a few swipes to kill someone. You don't have to do this back-to-back as long as its in one match. Gang matches are the perfect place to get throwing knives and the melee knife is also a good choice when you can't find a throwing knife.
DOUBLE BAGGER
Double capture 3 times in a single Gold Rush map.
Use the
Trophy Boosting Thread
You need at least three people including yourself to get this trophy. What you need to do it collect 2 bags of Gold while playing Gold Rush (Free For All) and drop it in the case 3 times. After you do it three times the trophy should unlock. Make sure you grab 2 bags before dropping them in the chest.
HEADHUNTER
Kill 5 players via headshot in a single Shootout or Gang Shootout.
This trophy can be done on the same player over and over. This trophy has be in a Shootout or a Gang Shootout match. Just aim for the head and it will unlock after your fifth headshot kill. It doesn't have to be right after each other, just has to be in a single competitive shootout Match
.
LEGENDARY 
Reach level 50 and pass into Legend.
This trophy can be earn at anytime, when you pass or if you already passed into legend. This trophy is retroactive, so if you already reached level 50 and passed into legend, you will still be able to get it. As soon as you buy the DLC and pop in the game and head in to an online free roam the trophy will pop.
For "Legendary," ONLY IF YOU ARE ALREADY RANK 50 AND DO NOT WANT TO PASS INTO LEGEND: copy the Multiplayer save file to a USB flash drive, then go into MP, then go to LAN, and pass to Legend there. The trophy CAN unlock in LAN. Once you get the trophy, quit the game, and copy back your old Multiplayer save file back and you will be at level 50 again. (Thanks
Yazter)
HAIL MARY
Get a kill greater than 35 yards with a Tomahawk.
This is a stressful trophy to obtain. There are many locations to get this trophy, so its best going for this trophy with someone you have on your friends list and not just any random person. This can be done on any player. Below are four easy locations to try to get the trophy at:
1.Start off a MacFarlane's Ranch and head down to where the horses are and have one player stand in the middle while you throw the tomahawk at him/her until the trophy pops. Keep in mind you have a limited supply of Tomahawks (ten to be exact).
2. You can head to Tensoro Azul and aim for the NPC that hangs out outside the door of the hideout. Make sure you are a good distance away.
3. Just outside Blackwater. Throw it at an NPC and you should be able to obtain it that way too. (Credit:
J3R3MY5)
Thanks to
RoosterTeeth for the video:
ORIGINAL GUNSLINGER
Get 25 Deadeye kills with Red.
When you first go online, press

, go to Multiplayer and then Outfitters. There will be a section that says Characters> Red Dead Revolver> and Red Harlow will be the first person. Press

and it will save. Return to Free Roam and look for some Deadeye while playing a Competitive Free For All match or Free Roam, then just kill 25 players using Deadeye.
Note: NPC's do not count, you have to kill real players while playing an online Free For All/Free Roam. The kills are cumulative so you can take as long as you need. It doesn't matter what maps you are on, it just matters what character you use to get the kills with this weapon.
REEEEAL GOOD
Get 25 Dynamite kills with Pig Josh.
When you first go online, press

, go to Multiplayer and then Outfitters. There will be a section that says Characters> Red Dead Revolver> Pig Josh is the fifth from the right. Same as
ORIGINAL GUNSLINGER, just with Dynamite. You don't have to use Dead Eye. Look for white ammo creates while playing online to restock Dynamite.