Join the Big Foot Gang.

Learn something about programming.

Raise your Reputation to Heavyweight.

Try to do 15 bench presses in a row.

Give him a can of cold beer.

Spend a total of $300 with him.

Have Strength that is a match for his.

Give him a slice of potato pizza.

Persuade three aquatic animal inmates.

Become a Negotiation Expert.

Watch three movies.

Participate in a prison boxing match.

Give him something to relieve his loneliness.

Challenge and beat him!

Join the Sharp Tooth Gang.

Try to persuade him to talk about himself.

Talk to him again after drinking some booze.

Have more Intelligence than him.

Read a book about fashion.

Join the Black Claw Gang.

Read a book about something weird.

Go to him if you are plagued by a nightmare.

Find a clue about Fenrir.

Become a Basketball Expert.

Give him one bar of scented soap.

Ask around about Lisa the accountant.

Give him $200 for his time.

Have 10 out of 10 Charisma.

Go to him when you are in Pain.

Befriend a lieutenant or boss in each gang.

Give him two premium cigarettes.

Give him two handfuls of coffee beans.

Talk to him again when you are in debt.

Become a Craft Expert.

Give him one nail bat.

Become a lucky guy.

Stay up all night in segregation.

Have 90 points of max Health.

Give him one spoon.

Give him three sleeping pills.

Join a kitchen game.

Complete Lethal Kombat II.

Try to persuade him not to attempt an escape.

Give him $200 to invest.

Have enough Agility to dodge eight swords.

Give him one jewel scarab.