Although stealing from a rich person to give to the poor might help them out short-term, in the long run you need to wonder whether or not that would truly help them in the only way that really matters - the cultivation of non-attachment, compassion, and wisdom. So would demonstrating that stealing was good and noble, or redistributing wealth so the poor could get fancy houses and obtain more sensual pleasures really helpful to them, or would it just perpetuate their suffering? Far more helpful I think would be going to teach the Dhamma to the poor with lovingkindness and compassion. If they're starving and in danger of actually dying, then I can understand why breaking the precept wouldn't be unthinkable, but there are always better options I think!
I think the "stealing is good if it benefits the poor" sounds reasonable, but that mindset where you attach "greater good" with "more material comforts and security" is born from conventional wisdom and not the Buddha's path.
Just my two cents.
Gain and loss, status and disgrace,
censure and praise, pleasure and pain:
these conditions among human beings are inconstant,
impermanent, subject to change.
Knowing this, the wise person, mindful,
ponders these changing conditions.
Desirable things don’t charm the mind,
undesirable ones bring no resistance.
His welcoming and rebelling are scattered,
gone to their end,
do not exist.
- Lokavipatti Sutta