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

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.social-bar --> </div><!-- .page-layout__social-share--header --> <div class="page-layout__main"> <p class="page-layout__image-credit"> <strong> Image credit: </strong> 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) </p><!-- .page-layout__image-credit --> <p>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:</p> <h2 class="wp-block-heading">Drew • 61 WAR</h2> <p>1997: <a href="https://www.baseballamerica.com/players/4577-j-d-drew/" target="_blank" rel="noreferrer noopener">J.D. Drew</a>, OF, No. 2<br>2004: <a href="https://www.baseballamerica.com/players/4578-stephen-drew/" target="_blank" rel="noreferrer noopener">Stephen Drew</a>, SS, No. 15</p> <p>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.</p> <h2 class="wp-block-heading">Upton • 49 WAR</h2> <p>2002: <a href="https://www.baseballamerica.com/players/4967-b-j-upton/" target="_blank" rel="noreferrer noopener">B.J. Upton</a>, SS, No. 2<br>2005: <a href="https://www.baseballamerica.com/players/5338-justin-upton/" target="_blank" rel="noreferrer noopener">Justin Upton</a>, SS, No. 1</p> <p>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.</p> <h2 class="wp-block-heading">Benes • 33 WAR</h2> <p>1988: <a href="https://www.baseballamerica.com/players/11355-andy-benes/" target="_blank" rel="noreferrer noopener">Andy Benes</a>, RHP, No. 1<br>1993: <a href="https://www.baseballamerica.com/players/11354-alan-benes/" target="_blank" rel="noreferrer noopener">Alan Benes</a>, RHP, No. 16</p> <p>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.</p> <h2 class="wp-block-heading">Young • 15 WAR</h2> <p>1991: <a href="https://www.baseballamerica.com/players/12518-dmitri-young/" target="_blank" rel="noreferrer noopener">Dmitri Young</a>, 3B, No. 4<br>2003: <a href="https://www.baseballamerica.com/players/5009-delmon-young/" target="_blank" rel="noreferrer noopener">Delmon Young</a>, OF, No. 1</p> <p>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&#8217;s nephew, Quentin, is <a href="https://www.baseballamerica.com/rankings/2025-mlb-draft-top-high-school-prospects/" target="_blank" rel="noreferrer noopener">also one of the top prospects</a> in the 2025 draft. </p> <h2 class="wp-block-heading">Weeks • 13 WAR</h2> <p>2003: <a href="https://www.baseballamerica.com/players/4990-rickie-weeks/" target="_blank" rel="noreferrer noopener">Rickie Weeks</a>, 2B, No. 2<br>2008: <a href="https://www.baseballamerica.com/players/12937-jemile-weeks/" target="_blank" rel="noreferrer noopener">Jemile Weeks</a>, 2B, No. 12</p> <p>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.</p> <h2 class="wp-block-heading">Other Prominent First-Round Brother tandems</h2> <p>2019: Josh Jung, 3B, No. 8<br>2022: Jace Jung, 2B, No. 12</p> <p>1998: Jeff Weaver, RHP, No. 14<br>2004: Jered Weaver, RHP, No. 12</p> <p>2012: Josh Naylor, 1B, No. 12<br>2015: Bo Naylor, C, No. 29</p> <div id="disqus_thread"></div> <div id="taboola-below-article-thumbnails"></div> <script type="text/javascript"> window._taboola = window._taboola || []; _taboola.push({ mode: 'alternating-thumbnails-a', container: 'taboola-below-article-thumbnails', placement: 'Below Article Thumbnails', target_type: 'mix' }); </script> </div><!-- .page-layout__main --> <footer class="page-layout__footer"> <div class="page-layout__footer-row"> <div class="page-layout__social-share page-layout__social-share--footer"> Share this article <ul class="social-bar "> <li class="social-bar__item"> <a 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From prodigious talent to a love for Francisco Lindor, the Brewers&#8217; top prospect has what it takes to make it big.</p> </div> <!-- .entry-card__excerpt --> <aside class="entry-card__meta meta"> <span class="meta__item meta__item--date" aria-label="Post date" title="Post date" > <svg xmlns="http://www.w3.org/2000/svg" class="icon icon--md"><use xlink:href="#svg-icon-calendar" href="#svg-icon-calendar" /></svg> <time class="published" datetime="2025-02-17T10:58:33-05:00"> February 17, 2025 </time> <time class="updated screen-reader-text" datetime="2025-02-17T10:58:35-05:00"> February 17, 2025 </time> </span> <span class="meta__item meta__item--ba-plus" aria-label="BA+" title="BA+" > <svg xmlns="http://www.w3.org/2000/svg" class="icon icon--ba-plus-badge"><use xlink:href="#svg-ba-plus-badge" href="#svg-ba-plus-badge" /></svg></span> </aside> <!-- .entry-card__meta --> </article><!-- .entry-card --> </div> <div class="curated-content-block__item"> <article class="entry-card entry-card--default post-1565953 post type-post status-publish format-standard has-post-thumbnail hentry category-minors category-news category-podcasts"> <a class="entry-card__image-wrapper" href="https://www.baseballamerica.com/stories/tigers-2025-top-mlb-prospects-deep-dive/"> <img width="768" height="576" src="https://i0.wp.com/www.baseballamerica.com/wp-content/uploads/2025/02/tigers.jpg?crop=0px%2C120px%2C876px%2C658px&amp;resize=768%2C576&amp;ssl=1" class="entry-card__image wp-post-image" alt="" decoding="async" srcset="https://i0.wp.com/www.baseballamerica.com/wp-content/uploads/2025/02/tigers.jpg?crop=0px%2C120px%2C876px%2C658px&amp;resize=768%2C576&amp;ssl=1&amp;w=320 320w, https://i0.wp.com/www.baseballamerica.com/wp-content/uploads/2025/02/tigers.jpg?crop=0px%2C120px%2C876px%2C658px&amp;resize=768%2C576&amp;ssl=1 768w, https://i0.wp.com/www.baseballamerica.com/wp-content/uploads/2025/02/tigers.jpg?crop=0px%2C120px%2C876px%2C658px&amp;resize=768%2C576&amp;ssl=1&amp;w=1024 1024w" sizes="(max-width: 768px) 100vw, 768px" /> </a><!-- .entry-card__image-wrapper --> <div class="entry-card__category"> <a href="https://www.baseballamerica.com/stories/category/podcasts/" class="meta__item meta__item--category" aria-label="Post category" title="Post category" > <span class="meta__type-indicator meta__type-indicator--post"> <span class="screen-reader-text"> Article </span> </span> Podcasts </a> </div><!-- .entry-card__category --> <h3 class="entry-card__title"><a href="https://www.baseballamerica.com/stories/tigers-2025-top-mlb-prospects-deep-dive/" rel="bookmark">Tigers 2025 Top MLB Prospects Deep Dive</a></h3> <div class="entry-card__excerpt"> <p>Geoff Pontes and J.J. Cooper take an in-depth look at the Tigers farm system entering the 2025 season.</p> </div> <!-- .entry-card__excerpt --> <aside class="entry-card__meta meta"> <span class="meta__item meta__item--date" aria-label="Post date" title="Post date" > <svg xmlns="http://www.w3.org/2000/svg" class="icon icon--md"><use xlink:href="#svg-icon-calendar" href="#svg-icon-calendar" /></svg> <time class="published" datetime="2025-02-17T09:29:30-05:00"> February 17, 2025 </time> <time class="updated screen-reader-text" datetime="2025-02-17T09:29:32-05:00"> February 17, 2025 </time> </span> </aside> <!-- .entry-card__meta --> </article><!-- .entry-card --> </div> <div class="curated-content-block__item"> <article class="entry-card entry-card--default post-1565943 post type-post status-publish format-standard has-post-thumbnail hentry category-fantasy category-minors category-news tag-roboscout"> <a class="entry-card__image-wrapper" href="https://www.baseballamerica.com/stories/roboscouts-top-100-fantasy-baseball-prospects-for-2025/"> <img width="768" height="576" src="https://i0.wp.com/www.baseballamerica.com/wp-content/uploads/2024/09/roman_anthony_TaylaBolduc-1.jpg?crop=145px%2C0px%2C2278px%2C1708px&amp;resize=768%2C576&amp;ssl=1" class="entry-card__image wp-post-image" alt="" decoding="async" srcset="https://i0.wp.com/www.baseballamerica.com/wp-content/uploads/2024/09/roman_anthony_TaylaBolduc-1.jpg?crop=145px%2C0px%2C2278px%2C1708px&amp;resize=768%2C576&amp;ssl=1&amp;w=320 320w, https://i0.wp.com/www.baseballamerica.com/wp-content/uploads/2024/09/roman_anthony_TaylaBolduc-1.jpg?crop=145px%2C0px%2C2278px%2C1708px&amp;resize=768%2C576&amp;ssl=1 768w, https://i0.wp.com/www.baseballamerica.com/wp-content/uploads/2024/09/roman_anthony_TaylaBolduc-1.jpg?crop=145px%2C0px%2C2278px%2C1708px&amp;resize=768%2C576&amp;ssl=1&amp;w=1024 1024w, https://i0.wp.com/www.baseballamerica.com/wp-content/uploads/2024/09/roman_anthony_TaylaBolduc-1.jpg?crop=145px%2C0px%2C2278px%2C1708px&amp;resize=768%2C576&amp;ssl=1&amp;w=1280 1280w" sizes="(max-width: 768px) 100vw, 768px" /> </a><!-- .entry-card__image-wrapper --> <div class="entry-card__category"> <a href="https://www.baseballamerica.com/stories/category/news/minors/" class="meta__item meta__item--category" aria-label="Post category" title="Post category" > <span class="meta__type-indicator meta__type-indicator--post"> <span class="screen-reader-text"> Article </span> </span> Minors </a> </div><!-- .entry-card__category --> <h3 class="entry-card__title"><a href="https://www.baseballamerica.com/stories/roboscouts-top-100-fantasy-baseball-prospects-for-2025/" rel="bookmark">RoboScout&#8217;s Top 100 Fantasy Baseball Prospects For 2025</a></h3> <div class="entry-card__excerpt"> <p>Dylan White digs into 2024 data to present the top fantasy baseball prospects RoboScout is targeting heading into 2025.</p> </div> <!-- .entry-card__excerpt --> <aside class="entry-card__meta meta"> <span class="meta__item meta__item--date" aria-label="Post date" title="Post date" > <svg xmlns="http://www.w3.org/2000/svg" class="icon icon--md"><use xlink:href="#svg-icon-calendar" href="#svg-icon-calendar" /></svg> <time class="published" datetime="2025-02-17T08:38:36-05:00"> February 17, 2025 </time> <time class="updated screen-reader-text" datetime="2025-02-17T08:40:07-05:00"> February 17, 2025 </time> </span> <span class="meta__item meta__item--ba-plus" aria-label="BA+" title="BA+" > <svg xmlns="http://www.w3.org/2000/svg" class="icon icon--ba-plus-badge"><use xlink:href="#svg-ba-plus-badge" href="#svg-ba-plus-badge" /></svg></span> </aside> <!-- .entry-card__meta --> </article><!-- .entry-card --> </div> <div class="curated-content-block__item"> <article class="entry-card entry-card--default post-1347471 post type-post status-publish format-standard has-post-thumbnail hentry 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.entry-card__excerpt --> <aside class="entry-card__meta meta"> <span class="meta__item meta__item--date" aria-label="Post date" title="Post date" > <svg xmlns="http://www.w3.org/2000/svg" class="icon icon--md"><use xlink:href="#svg-icon-calendar" href="#svg-icon-calendar" /></svg> <time class="published" datetime="2025-02-17T07:06:39-05:00"> February 17, 2025 </time> <time class="updated screen-reader-text" datetime="2025-02-17T07:10:57-05:00"> February 17, 2025 </time> </span> </aside> <!-- .entry-card__meta --> </article><!-- .entry-card --> </div> <div class="curated-content-block__item"> <article class="entry-card entry-card--default post-1565306 post type-post status-publish format-standard has-post-thumbnail hentry category-college category-news"> <a class="entry-card__image-wrapper" href="https://www.baseballamerica.com/stories/18-standout-college-baseball-pitchers-from-opening-weekend/"> <img width="768" height="576" 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768px" /> </a><!-- .entry-card__image-wrapper --> <div class="entry-card__category"> <a href="https://www.baseballamerica.com/stories/category/news/college/" class="meta__item meta__item--category" aria-label="Post category" title="Post category" > <span class="meta__type-indicator meta__type-indicator--post"> <span class="screen-reader-text"> Article </span> </span> College </a> </div><!-- .entry-card__category --> <h3 class="entry-card__title"><a href="https://www.baseballamerica.com/stories/18-standout-college-baseball-pitchers-from-opening-weekend/" rel="bookmark">18 Standout College Baseball Pitchers From Opening Weekend</a></h3> <div class="entry-card__excerpt"> <p>These 18 college starters range from premium prospects to new arrivals who impressed over the first two days of action. </p> </div> <!-- .entry-card__excerpt --> <aside class="entry-card__meta meta"> <span class="meta__item meta__item--date" aria-label="Post date" title="Post date" > <svg 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datetime="2025-02-11T15:12:21-05:00"> February 11, 2025 </time> <time class="updated screen-reader-text" datetime="2025-02-11T15:12:23-05:00"> February 11, 2025 </time> </span> </aside> <!-- .entry-card__meta --> </article><!-- .entry-card --> </div> <div class="curated-content-block__item"> <article class="entry-card entry-card--default post-1559748 post type-post status-publish format-standard has-post-thumbnail hentry category-college category-news category-podcasts tag-college-podcast"> <a class="entry-card__image-wrapper" href="https://www.baseballamerica.com/stories/college-podcast-introducing-64analytics-our-favorite-opening-day-matchups/"> <img width="768" height="576" src="https://www.baseballamerica.com/wp-content/uploads/2025/02/64analytics.jpg" class="entry-card__image wp-post-image" alt="" decoding="async" loading="lazy" srcset="https://www.baseballamerica.com/wp-content/uploads/2025/02/64analytics.jpg?w=320&amp;crop=0,0,100,240px 320w, 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