In 1983, a then 36-year-old Donald Trump attempted to buy the Cleveland Indians from Steve O'Neill, who'd bought the team in 1978 but was known to be interested in selling. Kenneth Molloy, a New York attorney, sent a letter to Gabe Paul, the Tribe's president at the time, stating that Trump was offering up to $13 million for the team.
That offer was declined, but O'Neill passed away that August, and talks of the team being sold intensified. Trump eventually upped his offer to more than $30 million, but it was believed by many involved with the situation that if allowed to own the team, he would move them to Tampa at the soonest date possible. We might have been very close to Joe Carter, Tom Candiotti, Brett Butler, and Julio Franco stripping pieces off a cardboard cutout of a naked Donald Trump as the Tribe attempted to block a move by winning the whole @#$% thing.
The O'Neill family was against allowing that to happen, and it doesn't seem as though even Trump's highest offer was seriously considered, because of his desire to relocate. Controlling interest in the team was eventually sold to Richard Jacobs for $35 million in 1986. Soon after that began the most successful stretch of Indians baseball in the last 60 years. The Tribe won five AL Central titles and two American League pennants under Jacobs' ownership, which ended after the 1999 season with the sale of the team to Larry Dolan.
Ownership of the Indians has tended to be a very temporary things over the course of the team's history. Jacobs became the Tribe's tenth owner different owner dating back to Bill Veeck's purchase of the team in 1946. If you don't count the time period during which O'Neill's estate controlled the team, none of those owners kept the team longer than six seasons. It's almost certain that even if Trump had been successful in his bid to obtain the team, he'd long since have sold them off. If he'd kept the team in Cleveland and stuck around long enough to see the new stadium built, the Indians might still be playing in Trump Field.
The Dolan family has now owned the team for over 16 years, which is the second-longest tenure of any ownership group in franchise history, behind only that of the consortium led by Alva Bradley, which owned the team from 1927 until 1946.