These are achievements you'll pick up as you move through the game's storyline - each comes from completing a particular mission or chapter.
Somethin' I've Gotta Do - Get your things from Sammy's.
Pray On the Way Up - Takeover Delray Hollow.
For Old Time's Sake - Recruit Cassandra.
Fish Gotta Eat - Takeover River Row.
We Partners Now - Recruit Vito.
It's a Brave New World - Takeover Pointe Verdun.
Cut and Run - Recruit Burke.
Sure Thing, Boss - Recruit all three underbosses.
Everyone Will Notice - Takeover Downtown.
Little Late for That - Takeover Barclay Mills.
The Connectino to Cuba - Takeover Tickfaw Harbor.
Certainly Was Exciting - Takeover Frisco Fields.
Burn Like Napalm - Takeover Southdowns.
Real Nice Time - Takeover The French Ward.
The Poor Sumb**** - Execute the judge.
There's a War Goin' On - Execute the radio host.
Jesuit in New Mexico - Rescue the counterfeiter.
My Name is Lincoln Clay - Execute a specialist.
Yet Here We Are - Takeover New Bordeaux.
Before They Bury You - Complete the game, one way or another.
Optional Story Achievements
You can complete the game without doing these missions.
.45 In My Hand - Complete Cassandra's Optional Mission.
IRA Don't Ask - Complete Burke's Optional Mission.
I Need A Favor - Complete Vito's Optional Mission.
These don't happen automatically - you have to accomplish something in-game to pop them.
Cash in Hand - Save $150K in total between your wallet and your savings. Grab loose cash and upgrade rackets, or just wait - eventually the endless flow of kickbacks will buoy over the line.
Baby, You're a Rich Man - Earn $500K. As above.
Hole in Your Pocket - Spend at least $500K. Easy enough, if you have the above achievements. If some of the perks you want to spend on aren't availalbe, run side missions or optional missions for the relevant underboss until they are.
Racketeer - Raise a Racket to Max Earn. Do this by running any of the Side Missions.
Big Earner - Receive a $10,000 Kickback from an Underboss. You have to donate the bulk of the city to one underboss to make this happen, so be ready for whining and/or bullets from your other minions.
Live Another Day - Recruit all the racket informants, which is to say, always do the 'Interrogate' missions , and don't kill any of 'em.
Can't Trust a Rat - The exact opposite. Always do the 'Interrogate' Missions, but kill every last one.
The New Boss - Similar to the preceding - recruit all possible racket bosses. Note that some are killed by story fiat, but the achievement won't hold that against you. You will, however, need to wiretap the rackets in question in order to turn the bosses, so try to do that before even starting operations against a given racket.
No Loose Ends - Kill all the Racket Bosses. A real blow for your kickback earnings, but I suppose you save on fuses.
Custom 358 - Maintain a speed of 120 mph or faster for 20 seconds. Once you unlock the DeLeo Traviata (by taking over Tickfaw Harbor), you'll get this without trying. If you buy all the vehicle upgrades and unlock the Traviata, you'll get without even thinking about it.
Testing the Shocks - Jump at least 50 meters and land on your wheels. Often pops accidentally while trying to get the previous achievement. At those speed, even the arch of a bridge can give you sufficient lift - I used the highway into Delray Hollow for mine.
One Good Turn - Make a 180 degree at high speed without hitting anything. The Traviata remains a good choice - practise this one either in the open lots of Tickfaw or the sandy shores of the southern Bayou.
New Bordeaux Drifter - Drift for at least five seconds. The detector on this is a little odd - swerving from side to side counts, and the dirt roads and beachs of the bayou are ideal for this.
Wrecker - Execute ten Vehicle Takedowns. If you didn't get them in the main storyline, you're probably going to have to go after some cops, because Vehicle Takedowns don't work against non-combatants. Try not to think of Father James.
Combat Specialist - The descriptions says you need to kill 300 enemies with Takedowns, but non-lethal takedowns work just as well.
Shh, shh - Execute 100 Stealth Takedowns. Again, lethal or non lethal work equally well.
Closed Casket - Execute 50 Brutal Takedowns
Sending a Message - Do three Brutal Takedowns very quickly. You have enough time to sprint between enemies, and shoulder-charges seem to count toward the goal. Just try to have a tac vest on.
Never Saw it Coming - Kill an enemy within two seconds of kicking in a door. Use Intel View to line up your shot first. There's a good opportunity in the Rescue Stephen Degarmo mission, among others.
Flambe - Make ten enemies die by their own Molotovs. The key is to shoot-but-not-kill a goon as they're about to throw a Molotov at you. Luckily, they're pretty vocal about their intentions, so you have that going for you. Unluckily, only early-game enemies throw Molotovs, so you either have to commit to this one early, or wait for your next go-round.
Recruited to 5th SFG - Excute five headshots in five seconds. The Screaming Zemi is the key to this one, though to get a sufficient concentration of enemies, you may need to knock over a police station. A couple times. Easiesr to get in the early game, when enemy heads are softer.
I'm Goin' In! - Attacked a racket without killing any Enforcers. Can be achieved on pretty much any racket- there are always other ways to earn damage money. Keep in mind that these enforcers will add strength to the final safehouse guard.
Softened 'Em Up - Killed all the Enforcers for a Racket. Easy to pick up in the normal course of affairs. Some Rackets only have one Enforcer to begin with.
Bon Appetit - Fed a corpse to a gator. You can get this one within the first few minutes of the game
Next Time Swim Faster - Feed yourself to a gator. Can also be gotten in the beginning of the game, and many, many times afterwards.
Standard Communications Grid - Wiretap the Smack Racket in Delray Hollow. Practically a story mission, though the game doesn't actually make you do it.
Code 112 - Steal a police car. Plenty of opportunities for this one. Just be sure to stash your cash-on-hand first, yeah?
These Achievements aren't made obvious until you achieve them. Or read about them here.
Trust - Reach the Loyal state with one Underboss. Increase loyalty by award rackets, districts, and performing Side Missions and Optional Missions
Family - Reach the Loyal state with all your Underbosses. As above, but times three. Maintaining a sensible three districts per boss split is the easiest way to achieve this.
We're In This Together - Conquer New Bordeaux without any of your underbosses turning on you. Again, the 3 for 3 split is ideal.
Just You and Me - Cause two underbosses to turn against you. The surest way is to give all districts to a single underboss, while the others gnash their teeth and wail.