[2][4] Cutshaw served under General Jubal Early during the Valley Campaigns of 1864, but missed the Third Battle of Winchester as he was raiding behind Federal lines in newly-established West Virginia.

As Confederate defeat seemed inevitable in 1865, he received a severe leg wound during the Battle of Sailor's Creek, three days before General Robert E. Lee's surrender at Appomattox.

[2] Between 1865 and 1873, Cutshaw held several jobs, including professor at Virginia Military Institute and assistant to Charles P. Stone, engineer and superintendent of the Dover Coal and Iron Company.

[2] When Richmond's city engineer (and former Confederate captain), Charles H. Dimmock,[5] died in 1873, former General and Washington College President Robert E. Lee recommended Cutshaw as his successor.

He undertook numerous projects during his tenure, including the waterworks which pumped water from the James River and Kanawha Canal into the Byrd Park Reservoir, and was also heralded as a proponent of spaces for public recreation.

Not only did he oversee creation of the city's street grid and waterworks system, but he also oversaw significant architectural achievements, many in the then-popular gothic renewal style from locally quarried granite and which now are on the National Register of Historic Places.

[9] In 2015, the Virginia Department of Historic Resources erected a sign memorializing Cutshaw's civic contributions in Byrd Park in front of the round house, 621 Westover Road.