Pros
Brand caché. Everyone has heard of it - reads great on the resumé. Lots of history to work with. Some really talented coworkers, and a broad network of ex-coworkers throughout the city as a result. Opportunity to shift role/department if you find the right advocates. Promoted 3x in 5.5 years. Full 401K plan match. Retention stock bonuses possible.
Cons
Slow to adapt to new ideas, processes, technology. Year-end bonuses range from 1-3%, if you get one at all. Hangers-on from the good ole days dragged down the company, wasted time and money (decorated their apartments on corporate CCs, etc.) Ultimately, this lead to several rounds of brutal layoffs that still continued after I left (of my own accord). Truly devastating to sit through. Lots of young talent asked to leave the company in the interest of keeping nonproductive executives. The continued involvement of the family in the company is questionable, especially in the marketing department. Again, a lot of time and money is wasted on egos and self-referential ideas. Nothing truly innovative. Very much a "boys club" in the creative teams (advertising, web) and especially the editorial team.