Over my career in aerospace, I got to see a bit of the "old Boeing" and the "new Boeing", and even a bit of "old v new Boeing". I was mostly on the Defense side, but there was a story folks liked to tell (even though it wasn't quite right) about the 777, which was arguably the last product of the "old Boeing". Here's the story, with corrections afterward:
At the commit decision for the 777 in October 1990 (which is analogous to the DoD Preliminary Design Review), the McDonnell Douglas C-17 was in flight test at Edwards. When the first 777 was delivered to United Airlines in May 1995, the C-17 was...
...still in flight test at Edwards.
Fun story, and almost true. The dates on the triple seven are right, but there's a bit of exaggeration on the C-17. The C-17 had its PDR in 1985, but didn't enter flight test until September 1991, over a year late. So it was SUPPOSED to be in flight test at the 777 commit time. The C-17 also hit IOC (Initial Operational Capability, kinda the same as "in service", and it was apparently "kinda" an IOC) in January of 1995, but as I understand it, there was still testing at Edwards.
Regardless, the bottom line was that the 777 was developed and delivered in less than half the time as the C-17, and met a far larger fraction of its requirements. And what I saw was the "old Boeing", in Puget Sound, completely mobilized around the 777 development and flight test. Yeah, there was stuff that didn't go right, and no one will really say how close to on budget they were, but the 777 was a quality airplane, on time. This kind of commitment and mobilization just didn't happen with the 87, and likely won't ever happen again with Boeing. Alan Mulally ran the 777 program - he's the guy that later went and fixed Ford. Many folks think of this as the last solid Boeing program. The C-17 program, which did not meet a large fraction of the original requirements, was way over budget, and way behind schedule, and was run by Dave Swain and later Harry Stonecipher.
Flash forward a few years and there's a merger, and an evolution of the company. Ultimately, the folks who had previously excelled (Mulally and others) were pushed out, and Swain and Stonecipher and their mediocre pals ended up running things. A sad tale.
--Tony
PS - As an old Puget Sound Boeing guy, I do feel the need to point something out: some of the most effective engineering-focused program managers that I saw were heritage-McDonnell Douglas, and some of the worst business-school pablum-spewing "leaders" were heritage-Boeing, starting with Phil Condit - so the story is a bit more complex than "McDonnel Douglas ruined Boeing".