The one problem I see with the 757 is…it’s too damn heavy, and therefore basically a non-starter as far as airlines are concerned (at max takeoff weight, it actually got “heavy” added to the callsign because ATC had to provide extra spacing for wake turbulence). There’s no new engine in its thrust class (40,000 pounds, vs. 28,000 pounds for the Leap-1B engine powering the 737 MAX, or even 34,000 pounds for the heaviest A321s). That extra weight and thrust (if a new engine were to magically become available) comes at significant cost (i.e., fuel burn), which carriers were not willing to accept.
Despite the desires of aviation fans, the 757 is, in a way, like the 747 of narrowbodies. In other words, it was popular because for a long time it was the only plane in its class that could perform many of the routes airlines wanted it to do (for years, it was the only twin-engined narrowbody that could fly transcontinental US nonstop flights). It’s not that airlines wanted such a bulky plane, it’s that it was the only one available.
It should be telling that as soon as the A320 and 737NG came on the scene, 757 orders dropped almost to zero (and, after 9/11, literally to zero). Seriously, look at the order history. After 1990, it was pathetic.
It’s not because “Boeing priced the 737 cheaper.” Boeing had no reason to undersell their own product (how would that make any sense?). But, instead, the 737NG did most of what the 757 could do for a fraction of the operating cost, and airlines couldn’t justify the higher cost for what really amounted to a small percentage of their network that would take advantage of what the 757 offered. If Boeing didn’t do it with the 737NG, then Airbus would have taken over a lot sooner.
When Boeing isn’t an organizational mess, they can basically build as many 737s in two years as they built 757s in 25 years. In fact, the only Boeing-designed commercial jet type (i.e., not planes they inherited from McDonnell Douglas) that sold worse than the 757 was the 707 (and the 757 only edged out the latter by 40 planes total).
Romanticizing aside, the 757 was commercially a mediocre performer that was only “good” because its competition was 707s, DC8s, 727s, and either narrowbodies with too-short range, or too-expensive widebodies. Once the A320 and 737 grew into a 150-plus seat transcontinental plane, that’s where the airlines turned their focus, and they never looked back.
The 737 MAX isn’t even a fundamentally bad design. There’s nothing in the design that is causing Boeing and their contractors to build fuselages with hundreds of reported defects per year (this is, after all, basically the same fuselage they’ve been building for decades). There’s nothing in the design that is causing Boeing to shortcut the reporting of addressing those defects. And there’s nothing in a new design that would magically make them start building planes better (787, anyone?). Instead, they’ve screwed things up so many times because the company itself is in crisis, and has been for about 2.5 decades, and in that time, they’ve basically forgotten how to do the one thing that they do: build planes.