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He was shot to death February 28, possibly by outlaws, although debate continues about the circumstances of his death and the identity of his killer. The popularity Garrett had initially enjoyed for killing Billy the Kid decreased as the Kid's mythic status increased. His failure to give The Kid a chance to surrender was regarded as unfair.

For a while, he enjoyed the patronage of President Theodore Roosevelt. Roosevelt's own penchant for frontier life—he himself had hunted down three outlaws while acting as a deputy sheriff—attracted him to Garrett. However, Garrett's drunkenness as well as controversy surrounding the killing of The Kid quickly disillusioned him. Garrett nonetheless remains symbolic of an era when only a thin line separated the lawmen from the outlaws they policed.

At the time, the rich were considered by many to have robbed the poor in order to accumulate their wealth and some outlaws were popular because they targeted the rich.

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Garrett, on the other hand, targeted a popular outlaw. He grew up on a prosperous Louisiana plantation near Haynesville, Louisiana in northern Claiborne Parish, just below the Arkansas state line where he moved at age six after his father, John L. Garrett, purchased this and another cotton plantation Chamberlain , He left home in and found work as a cowboy in Dallas County, Texas.

In , he left to hunt buffalo. In , Garrett shot and killed a fellow hunter who charged at Garrett with a hatchet over a disagreement over buffalo hides. Upon dying, the hunter brought Garrett to tears by asking him to forgive him.