The arrival in Sheffield of Theodore Sedgwick in those
critical days must have lifted Colonel Ashley’s sagging spirits.
Here was young lawyer recently admitted to the bar of Berkshire
County who at 23 was 10 years younger than Colonel Ashley’s son
John. . .
Furthermore, his views in the early 1770s were almost
identical to Colonel Ashley’s. Both opposed American
independence, both upheld the dignity of the courts, and both
advocated peaceable conduct and avoidance of discord.
The self-confident, articulate Theodore Sedgwick often
joined Colonel Ashley in the paneled study upstairs in the Ashley
House to discuss the affairs of the town, the county and the
colony. There must have been something of a father-son
relationship between 23-year-old Theodore and the 60-year-old
colonel. Sedgwick brought to the discussions the most recent
legal opinions and an intolerance of common people whom he liked
to call “the shoeless ones,” while the colonel offered his vast
experience as selectman, judge, legislator and businessman.
They became colleagues in town meetings and county
conventions . . .
In the early 1770s the two lawyers spent many an evening
before a blazing fire warmed by the colonel’s good West Indian
rum or crystal-clear cider. At such times Mrs. Ashley’s servants,
Lizzie and Bett, hovered nearby to replenish the fire or the
decanter. (Chase, p. 15)