Sixteen seasons later, Roberts has earned himself a permanent place in Dodgers history as the third man to skipper Los Angeles to a World Series appearance. With an 11-1 victory over the Cubs in Game 5 of the National League Championship Series presented by Camping World, Roberts joined franchise icons Tommy Lasorda and Walter Alston as the only managers to reach the World Series in Los Angeles.
When Roberts first put on his L.A. cap, he never could have envisioned this.
"I was just trying to survive, just happy to be a Major League player at that point in time," Roberts said. "I think that as your kind of career evolves and starts to descend, you start changing roles -- mentor, teammate, role model, helping younger players and just loving the teaching component.
"I just love the game. I love to teach, I love the players."
With that in mind, there was only one logical next step for Roberts. He joined Bud Black's Padres staff in 2010 and spent five seasons in various capacities in San Diego until the Dodgers job came open after the '15 season.
In his first year in Los Angeles, Roberts took home the NL Manager of the Year Award, but fell a step short of reaching the World Series, losing to the Cubs in the NLCS. A season later, Roberts and the Dodgers flipped the script.
"To do what we did, it takes a lot of talent, a lot of give, a lot of open-mindedness," Roberts said. "There was a complete buy-in. Now, it's almost a culmination. Getting an opportunity to play for a championship, I'm just so proud of our guys."
It's clear his players responded when Roberts asked them to buy in.
"The energy he brings to the field every single day -- it's a genuine energy and passion and caring for every single guy in that room," said Justin Turner, who was named co-MVP of the NLCS along with Chris Taylor. "It's not a fake thing. It's real. I mean, he literally takes it upon himself, and he makes a point of trying to go and talk to every single guy every single day and ask how you're doing, how your family's doing."
To a man, Roberts' players rave about his ability to motivate.
But tactically, too, Roberts hasn't put a foot wrong this postseason. He's put on a clinic in bullpen management, bridging the gap from his starters to closer Kenley Jansen by exploiting every matchup possible. In 17 innings against the Dodgers' bullpen this series, the Cubs managed only four hits.
Lineup-wise, he's played those matchups pristinely, as well. Andre Ethier, Enrique Hernandez and Charlie Culberson all saw time in various platoons. And all three played critical roles in the Dodgers' NLCS success.