I haven’t found much of a convincing explanation, but here’s the OSI meeting notes from when it was approved:

[…] Matt Flaschen believes it complies with the OSD. The chief concern is that you can’t sell the fonts as fonts — you can only redistribute them as data included with a program. Seems like a restriction, but that’s what we’ve had on the Bitstream fonts for three or four years now and nobody seems to complain about them. Recommend: Approval

Source: https://opensource.org/meeting-minutes/minutes20090401

And I’m guessing, this is one of the Bitstream fonts that they’re talking about: https://en.wikipedia.org/wiki/Bitstream_Vera#Licensing_and_expansion

Certainly seems a bit at odds with the OSD to me:

1. Free Redistribution

The license shall not restrict any party from selling or giving away the software as a component of an aggregate software distribution containing programs from several different sources. The license shall not require a royalty or other fee for such sale.

Source: https://opensource.org/osd

I kind of agree that I don’t care as much. There’s not as much need for modifying a font, because it fundamentally cannot do as much as a program. And if a modification becomes necessary, that’s not going to need as much budget, so there’s not as much need for being allowed to sell it.

But at the same time, it’s not like the OSI is the judge over good vs. bad. Certainly would like to know Matt Flaschen’s thoughts why this fits the OSD…