The major factor for this lack of strength derived from this whirling layout is due to the positioning of the lettering. The 5 from 1928 has lettering centered on Lincoln. Though a much smaller scale than Jackson, Lincoln dominates the horizontal layout.
Though the upper font (SERIES OF 1928) looks and feels 90 years old, it neighbors nicely above the ageless look of WASHINGTON, D.C.
In most design, centering your major elements might result in diminished appeal. I say that in the case of these two designs, the tame decisions of 90+ years ago wins in a landslide. The above phrase "will pay to the bearer on demand" sure does help with the whole "cool" aspect as well.
The consistent use of fonts also helps the 1928 bill convey a strong composition. It has unquestionable Unity. All the information is obviously necessary but nothing seems forced or crammed. It all has its place and the viewer is comfortable with seeing it there.
Love how the 5 is nestled into the design on the older bill.
This strange circle element (found on the back of the '28 bill) is very cool.
Every coin or bill that hits my hand is scanned for a date. It is a habit that began when I collected old pennies as a young boy. I loved finding wheat pennies at my Grandparents' home. I'd search every time I stayed over. I am still in love with the look of those stems of wheat curving up the outer edge of the old pennies. Finding them never gets old.....