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The Best Rule 5 Draft Picks in MLB History

MLB’s Rule 5 Draft provides players with a unique opportunity. Over time, it’s proven that one team’s trash is another team’s treasure.

Breaking down the best Rule 5 Draft picks in MLB now and through big league history
Credit-MLB/AP/Joker Mag

Major League Baseball’s Rule 5 Draft provides an opportunity to players deemed “not good enough” for a team’s 40-man roster. In being selected, these players get a fresh start and a chance to crack the big leagues.

It’s a unique system.

Rather than toiling in the minors, players chosen in the Rule 5 Draft must remain on their new team’s active MLB roster for the entire season – or be returned to their former team (for a small fee).

While many of these picks don’t pan out, there are untapped talents and late bloomers who have slipped through the cracks.

These are the best Rule 5 Draft selections, now and throughout MLB history.

Table of Contents

Best Rule 5 Draft Picks of All-Time

Roberto Clemente – OF (1954)

Roberto Clemente was a Rule 5 pick of the Pittsburgh Pirates
Credit–Diamond Images/Getty Images

Every baseball fan has heard of the legendary Roberto Clemente. But do you know how he ended up with the Pirates?

Despite seeing the 19-year-old’s incredible talent – and knowing he was major league ready – the Brooklyn Dodgers signed Clemente to a minor league contract. Due to the weird bonus rule at the time, this left the heralded outfielder unprotected in the Rule 5 Draft following the season.

The Dodgers did their best to hide Clemente, giving him less playing time as the Triple-A season progressed, but to no avail. Pittsburgh made him the first selection in the 1954 Rule 5 Draft, and the rest is history.

R.A. Dickey – RHP (2007)

After the Rangers drafted R.A. Dickey in the first round in 1996, the team’s doctors discovered he was missing a UCL in his right arm.

It was remarkable he could even throw a baseball, let alone do it professionally.

Dickey struggled mightily at the big league level, posting a 5.57 ERA through his age-33 season. Realizing that time was running out, he started fiddling with a knuckleball.

When the Mariners chose him in the 2007 Rule 5 Draft, Dickey was still putting it together. A few seasons later, he landed with the Mets and, at 35-years-old, had the best season of his career.

R.A. Dickey would pitch seven more MLB seasons, winning a Cy Young Award in the process, before hanging up the cleats for good at 43-years-old.

Shane Victorino – OF (2002 & 2004)

Before becoming “The Flyin’ Hawaiian”, Shane Victorino was an unknown prospect who was a Rule 5 pick twice.

In 2002, the Padres scooped him from the Dodgers farm system. But, after Victorino hit just .151 in 36 MLB games, they returned him to Los Angeles.

After two more years in the minors, Victorino was again chosen in the Rule 5 Draft – this time by the Phillies. From there, he evolved into an All-Star, Gold Glove outfielder who played an integral part in two World Series Championships.

RELATED: Our Interview with 2008 World Series Champion & D3 Alum Chris Coste

Johan Santana – LHP (1999)

Originally signed by the Houston Astros, Johan Santana was another international prospect just trying to figure it out. The southpaw spent years in the minors, but couldn’t make it past A-ball.

After the 1999 season, the Astros left Santana exposed to the Rule 5 Draft – much to the dismay of Andres Reiner, the scout who discovered him.

“I really fought that,” Reiner told the New York Post in 2008. “I knew he would be taken. But I couldn’t convince the organization.”

In a pre-arranged deal, the Marlins selected Santana and immediately shipped him to the Twins. It took the lefty some time to put the pieces together, but he ultimately became one of the most dominant left-handed starters of his era.

Jose Bautista – INF/OF (2003)

Jose Bautista was a late bloomer.

Drafted by the Pirates in the 20th round in 2000, Bautista was scooped up by the Orioles as a Rule 5 pick a few years later. Baltimore gave up on him after 16 games and, in 2004, he became the first player in MLB history to appear on five different major league rosters in a single season.

Then, in 2010, Bautista landed in Toronto as a 29-year-old no-name journeyman. Everything changed.

A new approach at the plate turned him into one of the most prolific power hitters of the decade. Bautista finished his career as a 6-time All-Star and 3-time Silver Slugger.

Josh Hamilton – OF (2006)

The Rays’ #1 overall pick in 1999, Josh Hamilton was a can’t-miss prospect who veered off course.

“I’m a drug addict,” he told USA Today in 2006. “It’s not terminal, but there is no cure. It’s hell on earth. It’s a constant struggle. And it’s going to be like that for the rest of my life.”

Hamilton was in and out of rehab centers, fighting the toughest battle of his life, before getting a second chance. It came with the Cincinnati Reds, who acquired him via Chicago in the 2006 Rule 5 Draft.

It was a new opportunity, a fresh start, and a blessing he didn’t let go to waste. In nine MLB seasons, Josh Hamilton swatted 200 home runs, made the All-Star team five times, and won an AL MVP award.

Honorable Mentions:

  • George Bell – OF (1980)
  • Willie Hernández – LHP (1976)
  • Bobby Bonilla – INF/OF (1985)
  • Dan Uggla – 2B (2005)
  • Joakim Soria – RHP (2006)
  • Alexi Ogando – RHP (2005)

Best Active MLB Players Selected in Rule 5 Draft

Nestor Cortes Jr. – LHP (2017)

Nestor Cortes Jr. was a 36th-round draft pick of the Yankees who got snagged by the Orioles in the 2017 Rule 5 Draft. But the lefty struggled in his first 4 games as an MLB rookie, and Baltimore quickly cut ties within the first two weeks of the 2018 season.

He landed back in the Bronx before being shipped off to Seattle for international bonus money. But the Mariners also gave up on him after just one season.

The third time has been the charm for Nestor Cortes Jr. and the New York Yankees. He’s become a fan favorite and All-Star caliber starter for the Bombers.

Mark Canha – INF/OF (2014)

After several years in the minors with the Marlins, Mark Canha was a Rule 5 pick of the Rockies in 2014. Colorado later traded him to Oakland, where the versatile slugger made a name for himself by leading all AL rookies in RBIs.

Canha became a free agent after the 2021 season and inked a sizable deal with the New York Mets. After signing, he told reporters, “I think I was ready for the big stage…and I want that big stage and to show the world what I can do.”

Ryan Pressly – RHP (2012)

An 11th-round pick by the Red Sox out of Texas Tech, Ryan Pressly struggled as a starter in the minor league ranks. When the Twins picked him in the 2012 Rule 5 Draft, their main concern was his command.

“This guy definitely has the two pitches to pitch late in the game,” Twins pro scouting coordinator Vern Followell said. “Now, a lot more goes into it — throwing strikes, commanding (pitches), handling pressure in those situations.”

The hard-throwing righty took advantage of the new opportunity – molding himself into an elite high-leverage reliever. At the start of 2022, the Astros locked down their All-Star closer for at least two more seasons.

Ji-Man Choi – INF/OF/DH (2015)

Ji-Man Choi’s transaction history is an adventure. All in all, he’s been a part of six big league organizations since 2010.

Originally signed by the Mariners out of South Korea, Choi later joined the Orioles as a free agent before becoming a Rule 5 pick of the Angels in 2015. He also spent time with the Yankees and Brewers before finding a home in Tampa Bay.

Ji-Man has thrived with the Rays, endearing himself to baseball fans everywhere. In October of 2020, he became the first Korean-born player to record a hit in the World Series.

More notable Rule 5 picks:

  • Brad Keller – RHP (2017)
  • Darren O’Day – RHP (2008)
  • Odúbel Herrera – OF (2014)
  • Connor Joe – INF/OF (2018)
  • Tommy Kahnle – RHP (2013)
  • Anthony Gose – OF/LHP (2017)
  • Anthony Santander – OF (2016)
  • Marwin González – UTIL (2011)
Written By

Division III baseball alum (McDaniel College) and founder of Joker Mag. Sharing underdog stories to inspire the next generation.



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