ORLANDO, Fla. — As Randy Winn descended the stage following Tuesday’s MLB draft lottery, he was quickly met by senior director of amateur scouting director Michael Holmes. Winn, technically, hadn’t done anything, but a congratulations was still in order.
“He’s very excited about that if you saw his face and heard his voice,” said Winn, the Giants’ vice president of player development.
That excitement was well-warranted after the Giants landed the fourth overall pick in the 2026 MLB draft, leapfrogging several teams to land their first top-five selection since 2018.
“This is definitely a surprise to me,” Winn said. “It’s a welcome surprise.”
This will be the sixth time since the Giants moved to San Francisco that the Giants will have a top-five draft pick, the other selections be…
ORLANDO, Fla. — As Randy Winn descended the stage following Tuesday’s MLB draft lottery, he was quickly met by senior director of amateur scouting director Michael Holmes. Winn, technically, hadn’t done anything, but a congratulations was still in order.
“He’s very excited about that if you saw his face and heard his voice,” said Winn, the Giants’ vice president of player development.
That excitement was well-warranted after the Giants landed the fourth overall pick in the 2026 MLB draft, leapfrogging several teams to land their first top-five selection since 2018.
“This is definitely a surprise to me,” Winn said. “It’s a welcome surprise.”
This will be the sixth time since the Giants moved to San Francisco that the Giants will have a top-five draft pick, the other selections being Buster Posey (2008, No. 5), Jason Grilli (1997, No. 4), Matt Willams (1986, No. 3), Will Clark (1985, No. 2) and Joey Bart (2018, No. 2).
San Francisco would’ve had the 15th overall pick if the draft was ordered strictly by record (81-81), but the team had the 12th-best odds at landing the first overall pick at 1.01% since three teams were ineligible for a lottery pick.
The draft lottery began with the Cincinnati Reds being given the No. 18 overall pick; Winn knew that if the Giants’ name wasn’t called by No. 15, their pick would be in the top six.
Once the Kansas City Royals got the No. 6 pick and the Pittsburgh Pirates got the No. 5 pick, Winn allowed himself to start thinking about the possibility of getting the first overall pick. His attention, though, started to drift when text messages started flooding in.
“My phone was buzzing from former teammates of mine heckling me while I was up there,” Winn said. “I could name a few. It was actually a few of my Tampa (Bay) teammates sending me text messages saying, ‘Don’t screw it up’ and some other very nice things. ‘You look terrible up there.’ Those sort of things. Who needs enemies when you have friends like that.”
The 2026 MLB draft is months away, but it’s possible that the Giants’ farm system will be brimming with middle infielders by next summer. MLB Pipeline’s top four amateur prospects for next year’s draft — UCLA’s Roch Cholowsky, Fort Worth Christian’s Grady Emerson, Alabama’s Justin Lebron and Gulliver Prep’s Jacob Lombard — are shortstops.
The Giants signed shortstop Josuar Gonzalez, the top position player of the 2025 international amateur free agent class, in January, then drafted second baseman Gavin Kilen out of Tennessee in July. After signing Gonzalez this year, San Francisco is one of the favorites to sign shortstop Luis Hernandez, the top position player prospect of next year’s class, in January.
The Giants, of course, hope that they can avoid the draft lottery after finishing .500 or worse for a fourth straight season. But if another opportunity did arise, would Winn serve as the Giants’ representative again if the opportunity arose?
“I hope not,” Winn laughed. “I don’t want to wear out my magic — my one-year magic.”