Multiple fight triggers on one creature

Question

So with Tolsimir, Friend to Wolves forcing entering wolves to fight, if I make 4 2/2 wolf tokens and send all at an 8/8 I know they won't all fight it at once. But would the 8/8 still die? Was wanting to use him as my commander but I might have to switch for the other version for my token tribal.

Answer 1

Yes, if 4 2/2 creatures fight a single 8/8 creature, they will all die.

The "fight" keyword is defined in rule 701.12a:

A spell or ability may instruct a creature to fight another creature or it may instruct two creatures to fight each other. Each of those creatures deals damage equal to its power to the other creature.

So, in this situation, here's what happens:

1. 4 2/2 wolf creature tokens are created. Tolsimir's ability triggers 4 times.
2. The first triggered ability resolves, and one wolf fights the 8/8. The wolf deals 2 damage to the 8/8 and the 8/8 deals 8 damage to the wolf. The 8/8 now has 2 damage marked on it, and the wolf dies.
3. The second triggered ability resolves, and there is another fight. The 8/8 now has 4 damage marked on it, and another wolf dies.
4. The third triggered ability resolves, and there is another fight. The 8/8 now has 6 damage marked on it, and another wolf dies.
5. The fourth triggered ability resolves, and there is another fight. The 8/8 now has 8 damage marked on it, so it dies, and the last wolf also dies.

Answer 2

Damage stays on a creature; you don't need to deal damage all at once for a creature to die. That probably is the main question you're asking, so the answer to your question is "yes, the 8/8 dies", with the rest of my answer just being details/special cases.

Each time one of the 2/2 fights the 8/8, the 2/2 has 2 damage to apply. So unless the damage is prevented, that's 8 damage, and unless the 8/8 has Indestructible, having damage equal or greater than its toughness would cause it to die. AFAIK, the only way to remove damage is the cleanup step at the end of turn, Regeneration, and a permanent leaving the battlefield. Also, while you can't mark damage on a non-creature permanent^[1], if you deal damage to a permanent while it's a creature, and it later turns into a non-creature, the damage will remain marked, and if it turns back into a creature with damage greater than or equal to its toughness, it dies.

There is the further complication that players gain priority between the resolution of each trigger, so if the controller of the 8/8 has some way of removing damage, countering abilities, and/or increasing its toughness at instant speed, they can keep it from dying. Also, if they flicker the creature, then when it enters the battlefield, it will do so as a new object, so all the remaining triggers will fizzle.

For the most part, any response your opponent can do between the triggers they could also do before any of them resolve (for instance, if you were targeting a creature with a toughness of only 2, they could put four regeneration shields on it before any of the triggers resolve, and the creature would survive), but there are edge cases, such as things triggering off of creature deaths, where it matters. For instance, if your opponent has Inheritance, then when the first token dies, they can pay 3 and draw a card, and then they can cast that card before the second fight trigger resolves (assuming the card is an instant, has flash, etc.).

[1]You can deal damage to a planeswalker, but unless that planeswalker is also a creature, this will cause the planeswalker to lose loyalty counters, but won't cause damage to be marked on it.