Best MLB First-Round Brothers: Could The Hollidays Soon Join?

Image credit: ATLANTA, GA - JUNE 4: Justin Upton #8 of the Atlanta Braves greets his brother B. J. Upton #2 before the game against the Pittsburgh Pirates at Turner Field on June 4, 2013 in Atlanta, Georgia. (Photo by Scott Cunningham/Getty Images)

Jackson and Ethan Holliday will become the 14th pair of brothers to be drafted in the first round. Here are the highest-drafted brother tandems, listed with overall selection number:

Drew • 61 WAR

1997: J.D. Drew, OF, No. 2
2004: Stephen Drew, SS, No. 15

Both Drews starred at Florida State and had lengthy MLB careers, making them the most productive first-round brothers. While J.D. infamously did not sign with the Phillies in 1997, he was the fifth overall pick the following year. His .384 OBP is one of the highest marks of the past 25 years, and he contributed steady power and defense as a corner outfielder. Stephen was a standout defender who had a few good years with the bat. Their brother Tim also was a first-rounder, drafted 28th overall in 1997 as a high school righthander.

Upton • 49 WAR

2002: B.J. Upton, SS, No. 2
2005: Justin Upton, SS, No. 1

Both Uptons signed out of high school in Chesapeake, Va. B.J. was a graceful center fielder who stole 300 bases with good power. Four-time all-star Justin was a slugging corner outfielder who hit 325 home runs. They were teammates for three seasons with the Padres and Braves.

Benes • 33 WAR

1988: Andy Benes, RHP, No. 1
1993: Alan Benes, RHP, No. 16

Former Evansville standout Andy was the preeminent 1-1 college ace before David Price, Stephen Strasburg and Gerrit Cole came along. He won 155 games in 14 seasons, made an all-star team and finished top five for a Cy Young Award twice. Younger brother Alan had an injury-marred, eight-year MLB career. The Benes brothers were teammates for three seasons with the Cardinals.

Young • 15 WAR

1991: Dmitri Young, 3B, No. 4
2003: Delmon Young, OF, No. 1

Dmitri made a couple of all-star teams in 13 MLB seasons. Delmon shined brighter as a prospect—No. 1 overall in 2006—but was done as a regular by his mid 20s and out of MLB before turning 30. Note that Dmitri and Delmon’s nephew, Quentin, is also one of the top prospects in the 2025 draft.

Weeks • 13 WAR

2003: Rickie Weeks, 2B, No. 2
2008: Jemile Weeks, 2B, No. 12

Rickie set the Division I standard with a .473 career average at Southern. With the Brewers, he contributed power, speed and walks to three playoff teams. Hard hands held him back defensively at second base. Jemile was a stronger defender but didn’t hit enough to hold a regular job.