Tiger Woods' recent DUI arrest in Jupiter Island, Florida, has brought attention to his nearly three-decade relationship with former President Donald Trump. During the arrest, Woods told officers he had been speaking with Trump just before the incident. Their relationship began in 1997 when Trump invited Woods to his Taj Mahal casino. Over the years, it has shifted from a professional connection to a personal one, especially as Woods is now dating Vanessa Trump, Trump's former daughter-in-law. The two families have grown closer, with their children attending the same school and participating in junior golf events together. Woods has publicly defended Trump, emphasizing the importance of respecting the office of the presidency, regardless of personal feelings. Their bond was further solidified when Trump awarded Woods the Presidential Medal of Freedom in 2019. Following Woods' serious car crash in 2021, Trump expressed support for his recovery and maintained contact with him. Currently, Woods is taking a break from golf to focus on his health and to strengthen his relationship with the Trump family.