New Yorker wrote about the weakness of the Callery Pear in 2005. As they fall down down around us, they make up nearly 11% of all New York City trees.
In 2006 there was a report published about tree maintenance for the city. The Comptrollers Office blames the Parks Department for not following up on the tree reports in a timely manner. If you want a chuckle, look at page 9 of this report to find a lively disagreement on fault between the two departments.
I cannot find any further reference to the state of the trees of the city at this current time or a published history from the Parks Department of requests for tree service.
BUT in 1902, 79 dead trees and stumps were removed by the President of the Borough of Manhattan's Bureau of Incumbrances (page 20).
SIDEBAR: this is a phenomenal primary document, addressing removal of street car tracks; gas main installations; sewer cleaning or lack thereof by the incredibly named Board of Estimate and Apportionment; an appeal to make lighting part of the job of the Borough President, in addition to cleaning and maintenance of buildings; the widening of Park Row; the need for more public comfort stations; progress of the "repair gangs,"In 1999, the National Review called the Callery Pear a replacement to stave off the "hellish blight" of windy streets. The writer, Richard Brookhiser, couldn't resist calling the East Village "skanky."
At that time there were 20 miles of macadam and gravel roads and 22 miles of dirt roads in Manhattan.; 106,000 people attended the Rivington Street baths; the annual budget was $1.7 million.
Storms have ravaged the city periodically. In 2003, one storm caused 1,050 people to call in reports of fallen trees around the city. In October 2005 a London Plane Tree fell on a little red car, destroying it.
And finally, in one of the worst storms in our history, in 1910 13 people in the area died. Each had quite the singular experience including lightning strike, drowning, falling tree, falling smokestack, falling circus tent pole, and one 7 year old boy who died from FRIGHT. Details here transcribed from the NY Times.