Created some wrapper code to utilize the PokerHand class. Fully interactive from the command line! (and yes, it's a bit of a mess)

poker.rb

# Poker

require_relative "PokerHand.rb"

class Deck
  @@CLASSIC_DECK = ['2d','3d','4d','5d','6d','7d','8d','9d','Td','Jd','Qd','Kd','Ad'] +
            ['2h','3h','4h','5h','6h','7h','8h','9h','Th','Jh','Qh','Kh','Ah'] +
            ['2s','3s','4s','5s','6s','7s','8s','9s','Ts','Js','Qs','Ks','As'] +
            ['2c','3c','4c','5c','6c','7c','8c','9c','Tc','Jc','Qc','Kc','Ac']

  def initialize (num_of_decks = 1)
    @deck = (@@CLASSIC_DECK * num_of_decks).shuffle
    @num_of_decks = num_of_decks
    puts @deck.to_s
  end
  def shuffle_cards
    @deck = (@@CLASSIC_DECK * @num_of_decks).shuffle
    puts "Shuffling cards!"
    puts @deck.to_s
  end
  def deal (num_of_cards = 1)
    @deck.pop(num_of_cards)
  end
  def to_s
    @deck.to_s
  end
end

class PokerGame
  def initialize (decks = 1, player_names = ["Player 1","Player 2"] ) # take player names in as an array
    @deck = Deck.new(decks)
    @players = Hash.new()
    player_names.each { |p| @players[p] = PokerHand.new( @deck.deal(5).join(" ") )}
    @num_of_players = player_names.length
  end

  def new_game #shuffle the cards and deal a new hand to each player
    @deck.shuffle_cards
    @players.each_key { |name| @players[name] = PokerHand.new( @deck.deal(5).join(" ") ) }
  end

  def winner # evaulates and returns the winner, along with their winning hand
    name_of_winner = ""
    highest_score = 0
    @players.each_pair do |name, hand|
      if highest_score < hand.evaluate
        name_of_winner = name
        highest_score = hand.score
      end
    end
    return name_of_winner, @players[name_of_winner].hand
  end
  def show_hands
    @players.each_pair { |name, cards| puts "#{name} has #{cards.hand}"}
  end
end

# Game Play Loop

input = ""
puts "Welcome to the poker room!"
puts "Looks like you're new here, who's going to be playing today?"
player_names = []
while input != "done"
  print "Name ('done' to move on): "
  input = gets.chomp
  if input.downcase == "done"
    break
  else
    player_names << input.capitalize
  end
end
puts "Ok, we've added a few people to the room, welcome..."
player_names.each { |n| puts n }
puts "How many decks do you want to play with?"
input = gets.chomp
puts "Ok, shuffling #{input} decks and starting to deal..."

my_game = PokerGame.new(input.to_i, player_names)

puts "Here are everyone's hands:"
my_game.show_hands
puts "The winner is..."
winner, winning_hand = my_game.winner
puts "Congratulations, #{winner}, you won with #{winning_hand}!"

while input != "n"
  print "Deal again? (y/n): "
  input = gets.chomp
  if input == "n"
    break
  else
    puts "Dealing again..."
    my_game.new_game
    puts "Here are everyone's hands:"
    my_game.show_hands
    puts "The winner is..."
    winner, winning_hand = my_game.winner
    puts "Congratulations, #{winner}, you won with #{winning_hand}!"
  end
end