[Answer] A fourth generation family member of a squash dynasty, and a four-time all American at Tufts University now coaches at what \"Little Ivy\" college?

Step 1 : Introduction to the question "A fourth generation family member of a squash dynasty, and a four-time all American at Tufts University now coaches at what "Little Ivy" college? "

...Hint :Maine

[Answer] What is the generation name given to those born 1980's - 1996?

Step 1 : Introduction to the question "What is the generation name given to those born 1980's - 1996?"

...The group of people born between 1980's through 1996 are usually referred to as "millennials." They are often the subject of jokes, complaints and less-than-flattering Facebook and Twitter postings. They are often characterized as lazy, narcissistic and reluctant to commit to a job for any length of time. These are the kids who received "participation trophies" and had parents masquerading as "best friends" in many cases. The stereotypical millenials live in their parents' basements well past the age of 21. Source: LiveScience.com