For Reddit Intermediate Challenge 280

AnagramMaker.cs

using System;
using System.Collections.Generic;
using System.IO;
using System.Linq;

namespace Anagram_Maker
{
    class Program
    {
        static string remainingLetters;

        static void Main(string[] args)
        {
            string output = "";
            List<string> words = new List<string>();

            using (StreamReader file = new StreamReader("Dictionary.txt"))
            {
                string line;

                //Each line of this file is a new word
                while ((line = file.ReadLine()) != null)
                    words.Add(line.Trim());
            }

            string input = Console.ReadLine();
            int failed = 0;

            while (words.Count > 0 || failed == words.Count)
            {
                remainingLetters = input;

                foreach (string word in words.OrderByDescending(x => x.Length).Where(x => x.Length <= input.Replace(" ", "").Count()).ToList())
                {
                    if(remainingLetters.Trim() == "")
                        break;

                    if (CheckWord(remainingLetters, word))
                        output = " " + word;

                    else
                        failed++;

                    words.Remove(word);
                }

                if(output.Trim().Length > 0 && remainingLetters.Trim().Length == 0)
                {
                    Console.WriteLine(input + " -> " + output.Trim());
                    output = "";
                }
            }
        }

        /// <summary>
        /// Determines if you can make the word given the letters
        /// </summary>
        /// <param name="letters">
        /// A string of every letter you have
        /// </param>
        /// <param name="word">
        /// Word you wish to create
        /// </param>
        static bool CheckWord(string letters, string word)
        {
            foreach (char c in word)
                if (letters.Contains(c))
                    letters = letters.Remove(letters.IndexOf(c), 1);
                else
                    return false;

            remainingLetters = letters;
            return true;
        }
    }
}

For Reddit Intermediate Challenge 280