"So, welcome, and enjoy yourself.

"That sounded like ten thousand dollars landing on the table, to the note." - Reginald Van Winslow

Reginald Van Winslow is a supporting character in the Telltale game, Tales of Monkey Island. In Poker Night at the Inventory, he is the host of The Inventory and the the dealer of the poker tournament. He returns to his role of host in Poker Night 2, while GLaDOS takes up the role of dealer.


A man with a strange fondness for maps, Reginald Van Winslow made his debut in Tales of Monkey Island, the fifth game in the Monkey Island series.

His cheerful demeanor and his quest for useless knowledge make him the perfect choice for The Inventory's host, a role he assumed in Poker Night at the Inventory and Poker Night 2.

Reginald Van Winslow TriviaEdit

  • He is never referred to by name in Poker Night at the Inventory. All the characters (including himself) refer to him as the host (or, before corrected, the manager). He is listed as The Host in the credits as well. This was likely due to legal issues as Winslow was still owned by LucasArts.
  • He has the same voice actor as he does in Tales of Monkey Island, Roger Jackson.
  • In Poker Night 2, he refers to himself as Reginald Van Winslow, and he is listed as Winslow in the credits.


  • Heavy Weapons Guy

There seems to be no huge relationship with the Heavy, but there are times Heavy responds to Winslow which is only during the introduction and when he buys in the Iron Curtain. Winslow finds that Heavy's gun has no problem with buying in.

  • Max

With Winslow there seems to be no big relationship. Only when Max buys in with his gun and badge Winslow agrees to let Max buy in to the game. He is sad to let Max know they can't buy in with a cherry, because he likes them.

  • Strong Bad

Strong Bad seems to have a bit of dislike towards Winslow for having such a high price of buying in with money. If Strong Bad buys in with the Dangeresque, Too? glasses, Winslow agrees if only no one else has a problem with it.

  • Tycho

No interactions between the two noticed

  • Brock Samson

Winslow seems to be quite annoyed by Brock for treating the Inventory like a slaughterhouse. He also is very overjoyed by the Player for unlocking The Venture Bros. set despite Brock's protesting that it's a bad idea. He can sometimes anger Brock when saying that the Venture Bros set stays. He gets sad when Brock makes a comment that his buy in an useless piece of junk, mostly because he was expecting it to be a weapon of mass-destruction or an artifact of supreme power.

  • Ash Willams

There seems to be no relationship except for his disagreement to having the Army of Darkness set unlocked, to which Reginald is overjoyed.

  • Sam

No interactions between the two noticed.

  • Claptrap

There is only one hint about their relationship in the intro, where Reginald is expecting Claptrap to arrive at the Inventory. Claptrap introduces himself by outright insulting other players and calling them losers. Reginald didn't comment on the line Claptrap said, but it is heavily implied that everyone (including the sailor) was disconcerted by him; especially after he tried to hit on Moxxi, which seriously annoyed her.