Freerolls are very popular promotional tools that poker rooms employ. A freeroll is quite simple. The poker room sets up a tournament and adds a certain amount of money to the prize pool. Entry into the tournament is free, though is sometimes restricted to certain types of players.
Many players are attracted to freerolls because of the potential to win something for nothing. Some freerolls even award large prize packages such as an entry into the World Series of Poker. Freerolls are also a way for players to practice their multi-table tournament skills.
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When evaluating whether or not to participate in a freeroll, here are factors to consider, in order of importance:
The overlay is the single most important factor when evaluating a freeroll. The overlay is the prize pool divided by the amount of players that enter the tournament. For example, suppose a poker room hosts a $1,000 freeroll and 500 players enter the freeroll. The overlay for this tournament is $2 per player. Essentially, an average player has an expected value of +$2 for entering this tournament. The higher the overlay, the better.
When the prize of a freeroll is a tournament seat or a satellite entry, just substitute the cash value of the prize as the prize pool when calculating the overlay.
2. Requirements for Participation
A freeroll isn't truly "free" if you have to play a lot at the poker room to be eligible for the freeroll. The less requirements made to enter the freeroll, the better. While entering free WSOP satellites can be fun and exciting, don't get suckered into playing more than you normally would at a poker room just for the freeroll promotion, especially if the overlay isn't that great.
3. Tournament Structure/Size
In general, tournaments that allow for more post-flop play (instead of just pushing chips all-in preflop) enhance the "skill" element of poker. These tournaments are preferable for two reasons. First, being able to make postflop decisions allows players to practice their reads and other post-flop skills. Freerolls where most of the action is just "all-in preflop or fold" are not very helpful for practicing poker skills. Furthermore, when skill is valued more, the better players have an increased chance of winning the tournament.
It is difficult to tell which tournaments will allow for more post-flop decision-making than others. Most often, tournaments with a smaller number of entrants lead to a better structure. This is because players will find themselves in fewer situations where the blinds are high and the stack sizes are low, which tend to result in all-in or fold preflop situations.
4. Ease of Competition
At most sites' freerolls, the ease of competition is similar. I seriously doubt that a $1,000 freeroll at one site is going to be much easier than the $1,000 freeroll at another site. Furthermore, freerolls generally have a very strong "luck" factor since so many people enter these tournaments and the blinds are often very high in relation to the stack sizes. I wouldn't rate one places' freerolls much higher than another because one site tends to have softer games than the other.