The Battle of Black Point on December 18, 1835, was the first significant battle of the 2nd Seminole War, 10 days before Dade's battle. Even though there were other raids on plantations at Wacahoota and Volusia area, this is one where the Florida troops really took a hit.
But what Seminoles were involved in the battle? That has long been a mystery. One source credits Osceola, but the source is not from someone who was at the battle.
Here is how the Seminoles (or/and Miccosukee) operated as a military force during the beginning of the war. Yes, there were large battles that seemed to involve the whole Seminole nation, like a few of the battles on the Withlacoochee. And a few battles that involved several towns and leaders but probably not the whole Seminole nation, which is what I would consider Dade's battle.
But for the most part, and throughout the war, the Seminole warriors were broken up into small bands and seemed to operate out of certain areas. For example, at the beginning of the war, Coacoochee and Phillip raided along the St. Johns River and plantation is Volusia. Only at the beginning of the war do you see a general upraising of different groups of warriors attacking at the same time.
The Seminoles were limited on how they could operate, because their logistics was limited. They could not order 30,000 rations and forage from New Orleans to resupply their nation. They had to grow their own food, which means they had to store supplies before the war, and forage where they could. Or take food and supplies from the settlers and soldiers in raids. This would limit where they could operate and how far they could travel. Travel over long distances would be a great drain on food and supplies, and wear out the men and horses.
Looking at where Osceola conducted his battles and raids, every one was around what is today Marion County. (Fort Defiance was actually south of Micanopy in Marion County.)
Osceola was blamed for doing a lot of things, but I think the soldiers would credit him for their losses. If you want to be defeated, you want to be defeated by the best, so there is no question that you could have blundered and lost to a smaller known band or chief.
When you look at the battles where Osceola is definitely known to be at, they are actually not very many. And remember, Osceola was not a big town chief. Yes he did have "Powell's Town," but it was small and not very high in the Seminole hierarchy. Osceola was still fairly young, and he was more of an enforcer of the tribal laws instead of a town chief.
Osceola during the war:
He killed Chief Charlie Emathla on Nov. 26, 1835.
He killed Indian Agent Wiley Thompson near Ft. King, Dec. 28, 1835.
First battle on the Withlacoochee, Dec. 31, 1835.
Against Gen. Gaines' command on the Withlacoochee, Feb. & March 1836.
Battle at Ft Defiance, June 9, 1836.
Battle of Welika Pond, July 19, 1836
Battle at abandoned Ft Drane, Aug. 21, 1836.
Battle of Wahoo Swamp, Nov. 21, 1836. Lt. Prince says that Osceola was in the area but not engaged in the main battle.
Spring 1837--Osceola parleys peacefully at Ft Mellon.
Osceola said to have been with Abiaka and Coacoochee when they scattered the Seminole encampment around Ft Brooke, June 2, 1837.
Osceola captured under a flag of truce at Ft Peyton, Oct. 21, 1837.
So there are only about half a dozen battles where we are pretty certain that Osceola was a participant. He may have been at other battles, but subordinate under another chief.
So now we are back to the original question: Who was the Seminole leader at the Battle of Black Point?
It doesn't seem likely that it was Osceola.
It was not Coacoochee & King Phillip.
Very far from Jumper's village, as well as Abraham.
Although Micanopy was head chief around Paynes Prairie, we don't see him leading many battles except being a figure head. You don't hear about Micanopy being a dangerous warrior.
Maybe it was Alligator? He was close to around 60 years old and considered a very prominent leader. He was a prominent leader at Dade Battle and on the Withlacoochee. His town was originally around Lake City, but he moved further south in the 1820s. Could he have been around western Alachuca County? Sprague says that he was, and committing raids around Newnansville.
So we don't know for sure, and will never be certain, but it seems that Alligator is a good candidate to be the prominent Seminole leader at the battle of Black Point.