In 1998, the Colorado Rockies selected Matt Holliday in the seventh round of the MLB Draft out of Stillwater High School (OK). Holliday would go on to have a successful 15 year MLB career racking up 316 home runs, 1220 RBIs with a .299 BA / .889 OPS. The seven time All-Star also won four Silver Slugger Awards, a batting title (2007), NLCS MVP (2007) and won the World Series with the Cardinals in 2011.
For most ballplayers, this might be enough to hang your hat on. In the case of Matt Holliday, his legacy in the game is multi-generational. In 2022, his oldest son Jackson Holliday was selected #1 overall by the Baltimore Orioles. By age 20, Jackson would make his big league debut. In 2025, Jackson has become a productive member of the Orioles lineup, on track to be the starting second baseman for years to come. Just the other night, Jackson’s younger brother, Ethan Holliday, would be selected #4 overall by Colorado Rockies.
The Holliday Difference
By most accounts, Ethan Holliday was a steal at #4. Many expected Ethan to follow in his brother’s footsteps as the #1 overall pick, but Nationals opted to go with another Oklahoma high school shortstop, Eli Willits. Ethan Holliday was named Baseball America’s High School Player of the Year (2025), another honor he shares with his brother Jackson. He also earned the 2025 Gatorade Oklahoma Baseball Player of the Year, an award also given to Jackson as well as his father (Matt) and uncle (Josh). Ethan hit .611 / 2.038 OPS with 19 home runs and 64 RBIs in his 33 game senior season.
One major difference between Ethan and Jackson is their size. Jackson’s 6 foot, 187 lbs made his transition to second base somewhat natural. Ethan stands 6’4″ and 215 lbs, very much the mirror image of his father in terms of size. Ethan could indeed remain a shortstop as he works his way up through the Rockies system. However, should he be asked to move positions, he could easily end up as a corner infielder or outfielder.
The Family Business
There are several other things that make the Holliday family unique. Matt Holliday put a major investment into his two phenom sons. Building an in-home training facility, Jackson and Ethan had access to top-notch instruction from a young age. None of this means they were predestined to become high level prospects, but they fully took advantage of their natural abilities and resources at their fingertips.
All things considered, the Holliday family is what baseball is all about. It’s a game that bridges the generational gap like very few things in our society today. As fathers, we should be proud of what Matt Holliday has been able to see his boys accomplish at such a young age. As young ballplayers, Jackson and Ethan have the opportunity to be the most dynamic sibling duo in MLB history.
