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Despite the film being written by John Wick creator Derek Kolstad and the similarities between Wick and Hutch (both being highly trained assassins), there is no obvious implication that this takes place in the John Wick universe. In a recent interview, Kolstad did hypothesize a crossover idea that would just consist of Reeves' and Odenkirk's characters briefly nodding to each other in a passing fashion, so who knows what could happen in a future film...

The tattoo on Hutch's wrist, a Seven of Spades and a Two of Diamonds, is statistically the worst possible starting hand you can be dealt in Texas Hold 'Em, since they are the lowest two cards that cannot make a straight (there are four cards between 2 and 7), and both of them are off-suit. Meaning if you ever see these two cards, you should fold immediately, because you are most likely never going to win. In Tarot readings, the Spade/Sword is linked to bad luck, death, and violence, while Diamonds/Coins are linked to money. Translation: This man dealt in death and violence for money.

No, he did not. It's not Cillian Murphy. The actual actor playing the veteran is Stephen Eric McIntyre.

Yes, Harry is Hutch's adoptive brother. Both of them refer to David as their father.

I was expecting the line "You're free to leave" at the end of that scene. It was someone high in the government calling to tell the detectives to let him leave without charges. Probably.

Yes there will be, in 2025.