I've found an old conversation with a lawyer in the context of a due 
diligence audit, which led to the removal of older versions from 
SourceForge:

"You currently have iText 2.1.7 and older versions available on 
SourceForge. While those versions were available under MPL or LGPL, it 
has come to our attention that some of the code (which has been removed 
in the 5.0+ versions), cannot be verified as free of possible copyright 
violations. You took great steps to go through the entire code base and 
obtain general releases for all code when moving from the LGPL/MPL 
version to the AGPL version. There is code in older versions (that no 
longer exists in version 5.0) which could pose indemnity problems for 
organizations. This is for your information only, we are not directly 
aware of any situation, only aware of the possibility since no waivers 
could be obtained from the organization(s) and individual(s) who 
contributed the code and the actual source of this code could not be 
identified."

In short: people who decide to use iText versions older than version 5+ 
are taking a risk. Not only are they using outdated software for which 
support has been discontinued years ago (which makes them look less than 
professional), it's also possible that they are investing time in 
software that could cause legal problems.

For instance: if you're a start-up, and you decide to use iText without 
a license, you should have a hard time when you go to a VC for funding, 
because they'll vet your code and you won't get any money if you aren't 
able to prove that you're entitled to use iText.

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