Orioles boast baseball's only two Will Robertsons

The Baltimore Orioles organization now includes both players ever named Will Robertson in baseball history. One is a recently claimed outfielder, while the other has risen through the front office ranks to become vice president of domestic scouting. The coincidence has already led to some humorous mix-ups.

In a quirky twist for the Baltimore Orioles, the team has assembled the entirety of baseball's historical roster of players named Will Robertson. There have only been two such individuals in the sport's records, and both now call the Orioles home.

The first is a left-handed hitting outfielder who was claimed off waivers from the Pittsburgh Pirates on December 5, 2025. This Will Robertson has accumulated 70 major league at-bats across stints with the Toronto Blue Jays and Chicago White Sox. He turned 27 years old on December 26, 2025.

The other Will Robertson, a right-handed hitting outfielder, was originally drafted by the Orioles in the 30th round of the 2017 MLB Draft. After reaching High-A Frederick in 2019 during three minor league seasons, he shifted to the front office. His career progression included roles as a scouting analyst, special assignment scout, and director of player personnel. In October 2025, he was promoted to vice president of domestic scouting.

In this new position, Robertson will oversee the Orioles' 2026 MLB Draft in July, where the team holds the seventh overall pick following the Winter Meetings lottery on December 9, 2025. Reflecting on the draft position, he noted, “Obviously, higher is better. I would have loved to have seen a better number, but we just control what we can control.” He emphasized the ongoing evaluation process, stating, “We’ve already seen a lot of these players over the summer and previous year. After January 15th is when I think we’re really going to have to hit the ground running.”

Robertson expressed enthusiasm for the role, calling it a “dream job” surrounded by experienced colleagues like president of baseball operations Mike Elias and vice president of player and staff development Matt Blood. He draws on his playing background for perspective, saying, “I think you can be a really good evaluator and baseball operations employee without having that scouting background. Maybe, if anything, I have some empathy or a perspective of what players go through.”

The two Robertsons have yet to meet, but the front office executive has fielded plenty of confusion. “I certainly got a lot of text messages about it,” he joked. “I’ve actually received Venmo requests meant for him, so I make sure that those get to the right destinations.” This lighthearted overlap underscores the small world of professional baseball as the Orioles prepare for the upcoming season.

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Illustration of MLB trade: Taylor Ward in Orioles uniform batting, Grayson Rodriguez in Angels uniform pitching, with team logos and stadium backgrounds.
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Orioles acquire Taylor Ward from Angels in surprise trade

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The Baltimore Orioles traded right-hander Grayson Rodriguez to the Los Angeles Angels for outfielder Taylor Ward late Tuesday night, marking the first significant MLB offseason deal. Rodriguez, a former top prospect hampered by injuries, heads to the Angels with three years of team control, while Ward provides Baltimore with a right-handed bat to balance its lineup. The move highlights the Orioles' concerns over Rodriguez's durability after he missed the entire 2025 season.

Brothers Willson and William Contreras will represent Team Venezuela in the 2026 World Baseball Classic, marking the first time siblings have suited up for the country in the tournament. The duo, who previously teamed up in the 2022 All-Star Game, expressed excitement about sharing the field and honoring their family. Venezuela's Pool D campaign begins Friday in Miami against the Netherlands.

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Veteran reliever David Robertson, 40, announced his retirement from Major League Baseball on Friday after 17 seasons across eight teams. Known for his clutch performances and nicknamed 'Houdini,' he earned one All-Star selection and a World Series ring with the Yankees. Off the field, Robertson's charitable efforts through High Socks for Hope have impacted thousands.

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The Baltimore Orioles are continuing to investigate trade options for infielders Coby Mayo and Ryan Mountcastle as Spring Training approaches. This comes amid a roster logjam exacerbated by Jackson Holliday's recent hamate surgery. While temporary openings exist due to the injury, long-term infield spots remain limited.

Rockies utility player Willi Castro has joined Puerto Rico's roster for the 2026 World Baseball Classic, marking the second MLB All-Star addition this week. The 29-year-old, who earned an All-Star nod in 2024 with the Twins, will make his WBC debut. This follows the inclusion of Nolan Arenado and with Francisco Lindor as captain.

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St. Louis Cardinals top prospect JJ Wetherholt is concentrating on his strengths this winter ahead of Spring Training, aiming to secure a spot on the major league roster. The 23-year-old infielder, MLB's No. 5 overall prospect, emphasized maintaining his natural swing despite early coaching on weaknesses. Teammates and coaches praise his potential to energize the lineup.

 

 

 

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