The unknown sections of his life creates a twenty or thirty-year gap often filled with stories and rumors. Among those put into question is his bonds with Mitsunari, since legends will proclaim they knew each other since they were serving under Hideyoshi in their youth. Stories commonly state Yoshitsugu was only a year older than Mitsunari, but speculation has been arising that he was actually much older or younger than his friend due to the mixed accounts of his roots. His age is at odds with the tales created for their relationship—romanticized to have occurred due to their close ages—and adds more mystery to Yoshitsugu. The contradictions have been so confusing that a rather radical theory has been emerging with a small portion of believers for their friendship. This story argues Yoshitsugu had died of his illness within a year of contracting it and that the Yoshitsugu at Sekigahara was actually a heavily ailed Hideyoshi in disguise. While an interesting concept, it needs to prove Hideyoshi had somehow survived his historically accepted death date and adds more fuel to the debate. In any case, speculation over whether the two men truly considered one another friends continues to this day.