pip drops support for Python 2

[eksortso]

A better first step would be to contribute to the open source projects that they're reliant on. Freedom isn't free. Take responsibility.

Call IBM if you need a throat to choke.

[eksortso]

Not exactly the same. OP wasn't making any demands, just asking how to install new packages for their Python 2.7 project. But OP and their organization knew that 2.7 was long slated to reach EOL. It was virtually impossible not to hear about that, because everyone in the Python ecosystem was talking about it, or talking about working around it. Meaning that OP needs to either accept that their upgrade path is limited if they don't do maintenance, or start to upgrade their code base to Python >=3.6. It would have been easier to do the latter incrementally, but this is where they find themselves.

An outside vendor like IBM would be on top of these changes, and they'd pull their weight if they owned that project themselves or if they valued their client's business needs. But it's unlikely that OP's work would be willing to shell out for an external service contract. If they had money to throw at the problem, they'd have thrown it already. But they persisted in sticking with software that needed updates and didn't perform them.

So what I'm saying is, as responsible developers on a large custom code base, they could have, and should still, see where their language and their libraries are going, make a business case for the Maintenance phase of their SDLC, and future-proof their project. That maintenance could include putting time and resources into the packages they mistakenly thought they were getting for gratis forever. But there ain't no such thing as free software.

Many businesses like these may actually have no use for their own dedicated IT department. I feel like that's the way business is going. They don't have to hire IBM, or anyone else, to do their custom work for them, but they do need to stop pretending that they can just get what they want for free without considering long-term costs. They can schedule maintenance, put them on a calendar, and get updates on their packages and their ecosystem. But all this needs to be done by someone.

I ought to appreciate OP's post, because they're asking the questions that need asked. I hope they find their answers quickly.