Swagger Jack runs Jack's Swagger Shack in Huggler Memorial Colosseum. It is also known as The Swagger Shop.

Swagger Jack

'Howdy, pard. If you've got the swagger, we've got the swag.'

Items Sold

Buy (50 swagger)

Buy (1,000 swagger)

Buy (2,000 swagger)

Buy (3,000 swagger)

Buy (5,000 swagger)

Buy (5,000 swagger)

Buy (10,000 swagger)

Buy (10,000 swagger)

Buy (2,000 swagger)

Buy (2,000 swagger)

Buy (100 swagger)

Buy (500 swagger)

Buy (500 swagger)

Buy (Y,000 swagger)

You must earn Y,000 swagger during a pirate season to purchase this item.

Buy (Y,000 swagger)

You must earn Y,000 swagger during a holiday season to purchase this item.

Buy (Y,000 swagger)

You must earn Y,000 swagger during an ice season to purchase this item.

Buy (1,234 swagger)

You must earn 1,234 swagger during a drunken season to purchase this item.

Buy (Y,000 swagger)

You must earn Y,000 swagger during bear season to purchase this item.

Buy (Y,000 swagger)

You must earn Y,000 swagger during a numeric season to purchase this item.

Buy (Y,000 swagger)

You must earn Y,000 swagger during an optimal season to purchase this item.

Buy (1,000 swagger)

You must earn 1,000 swagger during a school season to purchase this item.
(You probably don't ever want more than 11 of these.)

Buy (Y,000 swagger)

You must earn 1,000 swagger during a safari season to purchase this item.

Buy (X,000 swagger)

You have A swagger.

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You've earned B swagger during a pirate season, yarrr.You've earned C swagger during a holiday season, fun!You've earned D swagger during an ice season, brrrr!You've earned E swagger during a drunken season!You've earned F swagger during bear season! Jack casino swag shop coupon

You've earned G swagger during a numeric season!You've earned H swagger during an optimal season.You've earned I swagger during a school season!You've earned J swagger during a safari season!

Notes

On your first visit, if your character pre-dates the April 30, 2012 PvP update:
In honor of your dedication and skill during the long PvP Pre-season, the judges have awarded you a bonus!*:
You gain some swagger (+X)
- The amount of pre-season swagger awarded is (pretty flowers picked / 25) + (White Canadians consumed / 2.5), rounded down.
When you purchase something:

You trade some of your swagger for a slick new item!

You acquire.. something.

If you can't afford something:

You can't afford that! And don't think you can steal it either!

If you try to buy something that isn't for sale:

Jack Casino Swag Shop Coupon

That's not an item you can buy. Sociopath.

The price of the Essence of Annoyance increases each time you buy one. The first costs 5,000 swagger; the second, 11,000 swagger; the third, 18,000 swagger; and so on. You will be unable to purchase another until you use the one you have.
You can buy the Huggler Radio, Black Bart's Booty, Holiday Hal's Happy-Time Fun Book!, the Antagonistic Snowman Kit, Essence of Bear and the Manual of Numberology even if you are in Ronin or Hardcore.
You cannot spend swagger on other items while in Ronin. Swagger Jack informs you so:

The Obligations of Ronin prevent you from turning in your swagger right now.

Or in Hardcore:

The Tenets of Hardcore prevent you from turning in your swagger right now.

During special seasons, Swagger Jack has a different introduction (and sometimes, a different name). A special item is available for purchase only during that season, and you must acquire its entire purchase price in any season of that type in order to purchase it. The special swagger you've earned for that season only is displayed below your current total swagger.
Attempting to purchase a special season item without enough special swagger results in this message:
You must earn at least X swagger during <a(n)> <type> season to purchase this item.
If you have enough swagger to purchase more than one School of Hard Knocks Diploma, this message appears:
(You probably don't ever want more than 11 of these.)
During a pirate season, Swagger Jack's costume and introduction differ:

Swagger Jack

'Ahoy, mate. If you be having the swagger, we be having the swag.'

During a holiday season, Swagger Jack is on vacation:

Holiday Hal

'Happy Holidays! Jack's on vacation, but if you have swagger, spend it here to increase your Holiday Fun!'

During an ice season, Swagger Jack is being helped out by a helpful snowflake:

Flakey, the Helpful Snowflake

Casino del sol bingo. 'It looks like you're trying to spend some swagger..'

During a drunken season, Swagger Jack is unable to operate the shack:

Bart Ender

'Jack doesn't have his liquor license, so I'm helping out this season. What'll it be, buddy?'

During a numeric season, the Spirit of Paul Erdős is operating the shack:

Spirit of Paul Erdős

'I may not be with you physically, but let's collaborate on some purchases. Just make sure and credit me when you pub