Having managed Tiger Woods since 1998, Steinberg has been at his side for the incredible highs and the debilitating lows.
From ruling the golf world to personal crises, multiple surgeries and a descent to 1,199th in the world rankings.
The last 12 months have seen Woods mount an astonishing comeback, culminating in a first PGA Tour win in over five years at September's Tour Championship.
And while many thought the American's days at the top of the leaderboard were over, Steinberg insists the man himself never doubted he'd be back.
''Well it was obviously great for golf," Steinberg told CNN Living Golf's Shane O'Donoghue of Woods' win at Atlanta's East Lake Golf Club.
"It was exciting but Tiger expected that to happen."
'Did it happen sooner than anticipated?" added Steinberg, "maybe, but he had a plan, he had a vision, he stuck to it.
"Most importantly he stayed healthy and he played more golf than he thought he would play, more consecutive weeks than he thought he would play."
Woods' form throughout 2018 served as a warning for his rivals.
He briefly led July's British Open at Carnoustie before finishing sixth and ended as runner-up behind Brooks Koepka at the PGA Championship in August.
His stunning return to form has seen him climb [up] to 14th in the world rankings.
"You could just see as the season rolled around he was rounding into form," explained Steinberg. "But even as one of the greatest champions of all time, you still have to relearn and so continuing to put himself in that position I think allowed him to prove to himself it's right there, he's on the cusp of it.''
Through 20 years alongside Woods, Steinberg has seen first-hand the trials and tribulations of a rollercoaster career, and he's philosophical when asked what it has taught him.
''Be humble, appreciate the good times and realize that with good health and hard work you can overcome quite a bit and Tiger's done that,'' he said. ''I'm just happy for him, I'm happy for the game of golf too; it helps everybody when there's a healthy and competitive Tiger Woods out there.''
And while Woods' star appeal remains, the current incarnation of the world's most famous golfer feels more accessible and open.
''I feel like Tiger's embracing his popularity more than he ever has ... it's very genuine,'' added Steinberg. ''I think it's really resonating and connecting with the public, with the fans, the media. More people are embracing him now than ever.''
After helping Woods amass a fortune of $750 million, Steinberg is bullish about the future. After losing several endorsement deals following a series of scandals that began to surface almost a decade ago, Steinberg has been crucial in helping rebuild Woods' career.
Their hard work is paying dividends once more.
"Business is pretty strong right now and we're fortunate that we're in the position where we're assessing opportunities rather than chasing them. Interest in appearances around the world is booming once again,'' he said.
''We're certainly going to be a bit more sensitive and careful on long-haul trips. For the past 20 years Tiger has been one of the true global travelers for golf but I think he's just going to be more cognizant of his body, what makes sense for his schedule and just to make sure that he's healthy.''
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