Jesse James was born to be an outlaw – he just never succeeded at anything else

Somehow when Jesse discovered horse racing while living in Tennessee, I've wondered what his evangelical father would have said about it. Horse racing requires betting, which the Bible frowns upon. Nevertheless, Robert James would most likely disapproved of the way both his sons turned out – robbers and killers.

It's all Robert's fault – if he hadn't been so insistent on heading to the gold fields of California in 1850 and dying there, life would have been different for the James family. But then, Zerelda wouldn't have married Reuben Samuel and some of my current friends – descendants of the Samuel clan – wouldn't be here today.

Jesse adopted the name Dave Howard and settled in Humphreys County, Tennessee (west of Nashville). In addition to horse racing, Jesse tried to carry himself off as a gentleman farmer and grain speculator. He and Zee were popular and held many a party and attended many a church social – no one in their circle ever guessed their true identities.

Jesse was a chameleon and could adapt to any circumstance in which he found himself. Surprisingly, that was probably due to his years as a bushwhacker – pretending to be a Union soldier, getting out of difficult situations quickly and perfecting the art of escape from the robberies he committed.

Jesse's horse, Red Fox, was rumored to be the fastest in Humphreys County and one of the fastest in the state – only Jesse would have strived for that nugget. But it also served him a purpose – should he need a quick escape, Red Fox would be able to get him away and fast.

Jesse, AKA Mr. Howard, still had to look over his shoulder constantly and be on alert every minute. He always kept people from coming up behind him by standing with his back against the wall, or positioning himself at a table on the far side where he could look out at the room.

He carried a pistol at all times, though that was fairly common in the late 1870s. He was still Jesse, however, and there were a few occasions where he showed off his incredible marksmanship by killing a dog at a BBQ who had stolen some food and by joining a contest at a fair in which men were trying to shoot the flame off a candle. He also occasionally challenged another man, but would catch himself just in time and insert a little humor into the situation – narrowly avoiding a confrontation.

It went against Jesse's genetic make-up to behave. He just couldn't do it and he was very lucky to not have been discovered.

Meanwhile, Frank and Annie finally made it to Tennessee, where they rented some land near Whites Creek, just north of Nashville. It was said that Frank was known to put in at least 10 hours a day working the land. I'm sure it gave him plenty of time to think about the direction his life had taken and to thank his lucky stars that they were living a quiet life for a while.

Frank went by the name of Ben J. Woodson (there's that Woodson name again – the boy's paternal Uncle Drury's middle name was Woodson and it was Jesse's middle name too). Annie added an "F" to her name, making her Fannie Woodson.

This is one of the more famous photos of
Jesse James and is authentic. It shows what
he actually looked like at the age of about 28,
and is believed to have been taken in Nebraska.
Note the lines on his neck and ruddy complexion
 – he was probably quite tan from living outside
and looked older than his 28 years.

Jesse wasn't the only one who found it difficult to let go of the outlaw lifestyle of living on the run. Frank also had his troubles.

One day, a son of a neighbor came to visit Frank while he was in the fields planting corn. The young man yelled to Frank, who hollered back "who is it?" When the young fella didn't respond quick enough, he quickly found himself looking down the barrel of not one, but two six-shooters.

Frank's finely honed skills in his guerrilla and outlaw lifestyles also crept into play occasionally as when he would sit down to a game of poker. One friend said, "Although Frank (Ben) looked like a preacher, he could play poker like a politician."

Even Annie forgot herself. She once offered a neighbor woman an opportunity to pick an item from her jewelry box to wear to a party and the woman was astounded by the amount of high quality jewelry a simple sharecropper's wife had in her possession.

Still, no one ever suspected the friendly couple Ben and Fannie Woodson of any shady past or present. They were well-liked by all of their acquaintances, as were Jesse and his wife.

Typical Jesse, however, quickly got himself involved in one too many financial binds, overspent, and over-played several friends and business acquaintances, finding himself being sued for bounced checks and accruing other debts. The hot water was rising and he was chaffing to make a change.

He was used to earning money the quick way – by stealing it – not by the old-fashioned way of having to work for it.

Jesse got to feeling a little too bold and was letting his guard down too frequently and by December of 1878, he realized it was getting a bit too "hot" for him in Humphreys County. So, he packed up his family and headed to Nashville where he could reconnect with his brother.

In late 1878 or early 1879, Frank rented a farm east of the Clarksville Pike, northwest of Nashville, which stood on a knoll overlooking the pike. It created a great outlook for Frank to see who was approaching the property.

It was to Frank's new home that Jesse, Zee and their children headed after leaving Humphreys County.

I've found the following a very interesting description of the two men as something that fit not only their known personalities, but that of two men on the run from something very bad.

"They were very quiet men. They spoke very little and attended their own business ... Frank was the quieter of the two, though Jesse never talked a great deal ... Frank used to sit off by himself on the track (race track) and whittle a stick and seemed to think a great deal. Neither of the men ever joked and they laughed but little (proof that the art of living on the run and incognito was wearing on the brothers). They both gambled a great deal. They were said to play poker right smart and play all sorts of games big and little." (Aleck Ament, bartender at the Crockford Saloon, Nashville - Nashville Daily American, Oct. 12, 1882 edition)

Jesse was getting itchy again, however. He liked robbing trains and banks and he liked the lifestyle it afforded him. Early in the summer of 1879, he made a trip west of the Mississippi that took him to the railhead of the brand new Santa Fe line at Las Vegas – perhaps to look for a new place to settle down, far away from Missouri law enforcement, or to look for new gang members.

This photo has been circulating for a long time and alleges
that it is of Billy the Kid (left) and Jesse James (second from
right). It is not Jesse in this photo and clearly does not even
resemble him. There are tons of photos out there alleging to be
of Jesse and/or Frank and even some of their family
 and many of them are fakes.

It is said that while in Vegas, Jesse met another notorious man – William McCarty, AKA "Billy the Kid." However, one can rest assured that Jesse remained known as Mr. Howard during this meeting because of other, questionable people present.

Still, legend has it that Jesse did reveal himself to Billy the Kid and had sought him out to see if he would join the gang. But Billy was not into robbing trains or banks, he preferred rounding up the livestock of others and taking it for his own.

Something tells me no gang would have had enough room for the personalities of Jesse James and Billy the Kid.

It seems that Las Vegas was too big for the likes of Jesse, as he witnessed other gangs that had been lured to the wild western town – mostly known as the Dodge City Boys. They began robbing a number of stagecoaches and some trains, so Jesse hightailed it back to Missouri.

And there, back in his old stomping grounds ... Jesse assembled what would be the last James gang and the beginning of the end.