letters to his wife are clear in expressing his frustration with his troops and his desire to quit his commission as soon as he could find a replacement.
In November he requested to leave the military again, but the responses were bleak. John Hancock, at Congress in Philadelphia on November 30th wrote to Richard that he hoped the officer would stay at his post and that "the Loss of so brave and experienced an officer will be universally regretted as a Misfortune to all America."
His own brother-in-law and good friend Robert R. Livingston Jr (the Chancellor) was struggling north to Canada that month. On November 28th, they arrived at Ticonderoga, freezing and exhausted from the trip (perhaps they would have done better if they had brought more than "but one blanket" for the two of them), and Robert had heard of Richard's desire to resign as well. He wanted Montgomery to stay too.
"I do not know how to approve or blame your Desire of quitting the service," Robert wrote, "Your country still wants you...& yet the sacrifice you must make is such as can hardly be borne by a man of any sensibility or feeling, heaven direct you to what is best."
This paragraph must have either made Montgomery's heart sink or his blood boil. It's heard to know. Either way, not knowing where to find a replacement, Robert pushed his brother-in-law to stay at his post--even while the troops were deserting and returning their families wherever possible.
Long story short, Livingston and Franklin turned back south just a few days later, and Montgomery made plans to visit his wife at home during the winter, when the army would wait out the season, but he pushed on for now at the head of an army bound for Quebec. Only a month later, he was killed in battle.
Henry and John) put everyone at risk--not just his sister's husband.
It was all part of a dreadful fall and winter for Robert. While he was returning south from this horrible journey with Franklin, first his grandfather and then his father passed away at Clermont on December 9th. He felt the loss of his father very deeply, and wrote back and forth with his friend John Jay about it many times. Richard's death was just a few weeks later on New Year's Eve.
Did Janet fault her younger brother's role in encouraging Montgomery to stay in the army? If she did, it has not surfaced in any writings. Instead, she was with them often in the coming years, perhaps taking comfort in a shared loss.
For Montgomery it was too late. Remorse or blame could not bring him back. His farm and mill were out of his reach forever, and in spite of his reservations, he went down in history as a hero--the first officer to die in the American Revolution.