The American golfer has featured in three editions of the tournament as player or captain but has never claimed victory.
The US team captain admits he will "not ever recover from" the USA's loss to Europe following "one of the toughest times" in his career since the loss in New York.
This seasoned golfer captained Team USA in New York this past fall, witnessing a disappointing performance as Europe secured a narrow win.
His selection as captain made him the youngest captain for either team since the legendary golfer over six decades ago.
But he accepted he had made some wrong calls following his team selections and venue preparations were among the decisions questioned in the aftermath, as Europe became the initial squad to win away in over a decade.
"After the tournament, this has been among the most challenging moments in my life," stated the captain in his first news conference following the competition.
"You win, it's glory for a lifetime - but I didn't and I must live with this outcome for the rest of my life."
"I genuinely believe that this will ever fade. This tournament has been so brutal on me. I will always question and regret."
Notwithstanding a Dramatic Final Day Comeback Attempt
Despite a inspiring last-round rally effort, Team USA gave themselves too much to do after Europe established a 5½-2½ lead during the first day and extended that to a commanding lead after the second day - the largest margin going into the final day in recent tournament history.
And although the hosts won 8½ points in the individual contests, it wasn't enough.
"You put so much into it, and you have all this planning, and the first two days went as poorly as we could have ever thought," commented the captain.
Leader's Personal Struggles
Bradley had been expected to serve as both competitor and leader yet experienced a "change of heart" earlier this year and decided against competing at the venue.
"During the initial training session, I was out on the tee, observing the guys walk down the fairway as a group, and I said to myself 'I wish I was playing - that's what it's all about. I'm absent.'"
However, Bradley asserts his choice was correct in omitting himself from the team because he was "completely drained" after two days of competition.
"I simply believed I could do both jobs," he stated.
A History of Ryder Cup Disappointments
Bradley has experienced defeat in three Ryder Cups as a player and captain. He still hasn't unpacked his suitcase since the 2012 loss at Medinah and also was a member with the defeated American team at Gleneagles a decade ago.
And, although uncertain if he will get the chance again, he affirms he will persist to offer his services for future editions.
The next Ryder Cup will occur at Adare Manor in mid-September the coming years.