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It's all down to chance. I've been playing since OOTP 12 and I've had saves with 5 seasons played and no owner died or sold the team. I've also had saves where 3 different owners died in the first season. My only save so far in OOTP 19 I've had one owner die, in the first season (I think the Giant's owner?). This was before today's patch.
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