During the first year of the war he was active in driving out and maltreating Union men. Living quite a distance from Mr. Chittenden, he had never seen Grace until the time she went to the rescue of Mr. Osborne. He was one of the hanging party. When Grace so unexpectedly appeared on the scene, her excitement and fierce wrath only heightened her beauty, and Tom gazed at her in admiration. He had been one of the most violent in demanding the death of Mr. Osborne, but now he suddenly changed sides and demanded that he be let go. Much to Grace's disgust he persisted in paying her attention, and at length proposed. Much to his surprise he was not only refused but refused with scorn and contempt. This aroused every evil passion of his nature. "You will regret this, Grace Chittenden," he cried furiously. "I 'spose you reckon you be too good for me, but I will give you to understand that there is not a gal in the Ozarks, except you, but would jump at the chance to be my wife." "Go and make one of them jump, then. I want none of you," replied Grace sarcastically, as she slammed the door in his face, leaving him swearing and cursing. When Mr. Chittenden was informed of what had occurred he sent word to Tom never to set foot on his premises again. Mr. Chittenden was too big a man for even Tom to defy. But the affair got out and Tom, when he was not present, became the butt of the county over his presumption in aspiring to the daughter of Judge Chittenden. Tom knew of the merriment it caused and his pride was so hurt that he disappeared and was not heard of for over a year. In the fall of 1862 he suddenly appeared in the Ozarks at the head of a band of guerrillas. The band numbered about fifteen, and he concluded that with this force he would show Judge Chittenden that he was not afraid of him, and that he was as big a man as he was. Therefore, he rode boldly up to the house. He was mounted on a magnificent horse, an immense plume floated from his hat, and he was decked out in all the grandeur of a bandit chief. Mr. Chittenden was surprised, but concluded that under the circumstances it was policy to treat him with courtesy. Tom had learned to be polite. He did not mention past differences, or ask to see Grace. He had much to say of his prowess in the field, and of the number of Yankees he had killed, and boasted he held a commission as captain signed by General Price. The main object of his visit seemed to be to impress on the Judge his importance. When he learned Mr. Chittenden was engaged in gathering supplies for the Confederate army he proffered his services to help, which the Judge thought best to accept. He became quite a frequent caller at the house, and as he did not force his attentions on Grace, she thought it best to do nothing to anger him, but saw as little of him as possible. "Who is this fellow hanging around here?" asked Tom one day of Mr. Chittenden.