FREE Shipping on orders with two or more bags!

Two Filibusters and an Empresario Came to Texas

Nine Flags Coffee gets its name from the flags that “flew” over Nacogdoches, Texas at one time or another. 

I’m sure you’ve heard of the 6 Flags Amusement parks. You may not know that it was named for the 6 flags that flew over Texas.

But Nacogdoches, Texas is different. What’s the story about those 3 extra flags?

In the early 1800s, Nacogdoches was the largest town in Texas. Originally a catholic mission, the pueblo was founded by Gil Y’barbo in 1779. It quickly became known as a haunt for smugglers and ne’er-do-wells. There wasn’t a strong Spanish presence in the town, so Americans found it to be an ideal spot for bringing goods in from the States under the radar.

These were turbulent times. 

Lots of land but not a lot of people. This got the attention of Southern Americans on the hunt for cheap land.

Enter the filibusters. 

Now, many know the word ‘filibuster’ from the long-winded speeches given in congress which are used to keep legislation from being passed. This was famously depicted in the Jimmy Stewart movie “Mr. Smith Goes to Washington.” 

That’s not the kind of filibuster we mean here. 

A filibuster, in the early 1800s, was a person who tried to take over a region. 

In fact, a filibuster is one who attempts to take over a region where he is not a citizen, without the official support of his own country.

Maybe the most famous of the filibusters of the era, William Walker, didn’t try for Texas but attempted to take over portions of Mexico and Central America several times.

Still, in Nacogdoches there were two prominent filibustering actions which made a claim to the town and the greater region.

The Gutierrez-Magee Expedition

The first of these was the Gutierrez-Magee Expedition. 

Bernardo Gutierrez de Lara was a Spanish citizen, a blacksmith from the region of Nuevo Santander, the border area north and south of the Rio Grande which later became disputed territory between Mexico and the United States. He, like many citizens of New Spain, was angry over the execution of Father Miguel Hidalgo who spoke out against the crown. 

Gutierrez decided to take action, so he traveled to Washington D.C. in December of 1811 for support. The U.S. and president James Madison were entangled in a growing conflict with Great Britain. Gutierrez got an approving nod from the administration but not the backing he was hoping for and was directed to go to New Orleans to get help.

In New Orleans, Bernardo Gutierrez de Lara met Augustus Magee for the first time. They mustered a band of 130 men at Natchitoches, Louisiana, 90 miles from Nacogdoches. In early August of 1812, they easily captured Nacogdoches, the oldest town in Texas. 

This marks the first filibustering expedition to fly a flag over Nacogdoches. They chose a solid green flag. Calling themselves The Republican Army of the North, they swept south toward La Bahia, adding Spaniards, Americans, and Indians to their army. They successfully captured several towns but suffered from inner conflict. 

Augustus Magee soon came down with a fever and died and Gutierrez lost control of the group and was deposed as the leader of the movement, so he left Texas for Louisiana eventually joining up with another filibuster, James Long.

The weakened Republican Army of the North met a Spanish army fresh from Laredo and lost a crushing defeat at the Battle of Medina (August 18, 1813), the largest loss of life on Texas soil in history. The Spanish army took no prisoners; they saw their opponents as pirates. They killed every man they could catch, over 1000. Then, the Spanish marched into San Antonio and executed every last citizen who was suspected of supporting the rebellion. 

After that, they killed many in Nacogdoches. 

The green flag came down; the Spanish flag was raised once again. But its days were numbered.

The James Long Expedition

Back in Europe, Spain’s empire was unraveling. It’s war against France took a severe economic toll on the crown. This war began in 1793 and was interwoven with internal French strife in which the people demanded constitutional rule.

As the “Napoleonic Wars” kept Spain and other European powers occupied, James Long decided to make a grab for Texas (1819). Long, who had the benefit of Gutierrez de Lara in his command, gathered men and took over Nacogdoches. There, Long was proclaimed the president of the Republic of Texas (not to be confused with the Republic of Texas from 1836 - 1845).

Among those in the James Long Expedition were José Félix Trespalacios an escaped convict and James Bowie who will famously die at the Battle of the Alamo in 1836. 

Long also reached out to Jean Lafitte the pirate on Galveston Island. Lafitte turned him down. 

The Long Republic lasted about four months until many of the men got tired of the ordeal and left. Long himself escaped to  Natchitoches, Louisiana to escape capture.

In 1820, Long pulled together the resources for another go at it. But again men got restless and left. Though they took the La Bahia Presidio, the Spanish took it back four days later, taking Long prisoner in the process. The prisoner was moved from one city to another, finally ending up in a Mexico City prison.

When Mexican Independence was declared later in 1821, Long was still in prison. He appealed to the new Mexican president Iturbide. But before he could be heard, he was shot by a prison guard. Some believe that his former associate Trespalacios was behind the assassination. 

The Fredonia Rebellion


In 1820, Moses Austin drew up an agreement with the Spanish government to bring Anglo settlers from the United States into Texas. But before he could get started he came down deathly sick. On his deathbed, his son Stephen F. Austin, agreed to continue the plan.

New settlers from the states were required to be Catholic. Also, they had to swear an oath of loyalty to Spain (later Mexico). Nor were they allowed to own slaves. All of these requirements were broken regularly.

Plus, under this “Empresario” system, men or women would get a contract from the government to bring settlers onto large tracts of land. After the Mexican authorities took over from the Spanish, Stephen F. Austin, with the help of Haden Edwards, continued in his father’s footsteps. 

In 1826, Edwards got a contract from the Mexican government to settle 800 families in the Nacogdoches area. One of the items in the contract was that the Empresario was not to disturb people who were already living on land in the area. 

When Edwards got set up in Nacogdoches, he sent notice out that settlers who could not show proof of title to their land would get evicted. This didn’t sit well with people living there, some of them for more than a generation. They complained and they also forged documents to show title. 

Edwards got more belligerent and the people complained to the governor. He revoked Edward’s Empresario contract. 

Edwards had $50,000 riding on this venture which adjusted for inflation is about one and a quarter million dollars in today’s money. He was not about to back down easily and lose his investment.

So on December 21st 1826, Edwards declared Texas independent from Mexico. 

Of course Mexico responded with armed men from San Antonio who put down the rebellion in short order. Edwards escaped to Louisiana. 

A few years later, he returned to fight with Sam Houston in the Texas Revolution. 

The Nine flags over Nacogdoches carry history and stories in every thread. These are stories of people at their best and at their worst. They are stories of dogged determination, great gain, and powerful loss. They are Nacogdoches. They are Texas.