In 1977, the then-25-year-old skipper lost his first four games for the Newark Co-Pilots, the Brewers' New York-Penn League affiliate. Then, it rained.
"That couldn't have come at a better time," Holmberg later joked.
His team dropped the opener of a doubleheader to fall to 0-5 before taking the nightcap for his first Minor League win.
After the horrendous start, that Co-Pilots finished 43-29, mere percentage points behind Batavia (42-28) for a division crown.
"I always say that taught me that it's not how you start, but how you finish that's more important," Holmberg said. "It's amazing how you remember numbers like that."
Flash forward 35 years and the 61-year-old has a new number he won't soon forget. Holmberg recorded his 1,300th victory as a Minor League skipper Friday when the Bluefield Blue Jays beat the Burlington Royals, 7-5.
"It's a great milestone," said Holmberg, who owns a 1,300-1,207 record. "It's been a pretty good ride with over 2,500 games. You get to 500 wins and you're happy, but you don't know exactly what the future will bring. Then you get 1,000 and that's pretty neat. Then there's 1,100, 1,200 and now 1,300. You go from counting the wins by ones or tens to rounding to the nearest 100. It's pretty cool."
The milestone win came under circumstances remarkably similar to the first.
The Jays had dropped four of their previous five games coming into Friday's doubleheader, then lost the opener, 12-5. They watched a three-run lead turn into a 5-4 deficit in the fifth inning of the second game before tying it in the bottom of the frame and taking the lead on Jorge Vega-Rosado's two-run homer in the sixth.
"Winning can be like pulling teeth sometimes, especially at this level," said the man who has spent 25 years as a manager -- 24 with the Toronto organization -- and 10 as a coach. "We're five games below .500 (at 21-26), but that's baseball. We need to keep working and hopefully things will turn around a bit.
"Maybe 1,300 could have come a little earlier, maybe it would have come a little later. But it came tonight and I'm just excited about the whole thing."
Holmberg and his players calmly passed around a bottle of champagne to commemorate the big win. It was nothing like the postgame championship celebrations.
The big moment didn't come until later when Holmberg opened a package from his son, Kenny, a former Minor Leaguer and a coach with Class A Advanced Myrtle Beach. The younger Holmberg insisted the gift not be opened until his father actually achieved his latest milestone.
When Holmberg unwrapped his present late Friday night, he found an autographed bat from his son, congratulating him on the achievement.
"It's always nice to have someone follow in your footsteps," he said. "I'm putting that right near the door at home, so when people come in and ask, 'What is that,' I'll answer, 'Well, let me tell you a story.'"
The gift memorialized the latest achievement in a managerial career that has crossed paths with Major League stars Roy Halladay, Carlos Delgado, Cecil Fielder, Fred McGriff, Jeff Kent and Al Leiter, among countless others.
With players like those as well as his own perseverance and longevity, Holmberg noted he has a lot to be thankful for.
"If I had to go back over it, I wouldn't be able to talk about it for a minute or five minutes or half an hour," he said. "From that first year in Newark to Wil Browning's save tonight, I've just learned that what goes around comes around."
Browning got the final three outs for his third save, preserving the win for reliever Denny Valdez, who pitched 1 1/3 hitless innings.