Believe it or not, the Home Run Derby wasn’t always a big deal. In 1990, for instance, a group of eight of the era’s finest sluggers hit just five total home runs at Wrigley Field in a non-televised competition. That all changed in the 1990s, thanks to ESPN and a new era of stars that unwittingly made the Derby one of the biggest events on the baseball calendar.
There have been dozens of contestants over the years, but a handful rise to the top as the most accomplished and memorable of the derby era. Here are the ten best we’ve seen since the event was first staged in 1985.
10. Bobby Abreu
In 2005, Comerica Park in Detroit had a steadfast reputation as a true pitcher’s park, and there were concerns that the Home Run Derby there would be a non-event. Abreu, then with the Philadelphia Phillies, ensured that those fears would prove unfounded. Abreu hit 24 home runs in the first round which, even after the recent format changes and shift from outs to timed rounds, still ties him for the second-best round of all time. He went on to win the competition, largely on the strength of that round.
9. Yoenis Cespedes
A two-time winner, Cespedes hit big, towering shots with his intense swings. He had a 17-homer round in 2013, but ultimately won his back-to-back titles with a methodical approach as opposed to absolutely monstrous rounds that wowed fans and opponents alike. There’s something to be said for that more balanced approach, and while there have been three multiple-time winners, Cespedes is one of only two contestants to win in consecutive years.
8. Bryce Harper
There was, in fact, a time when Nationals fans did not boo at the mere mention of Harper’s name. Think back to 2018, when he won that year’s derby in front of his home fans at Nationals Park by knocking off Kyle Schwarber in the final round. The finale was one of the finest comebacks in derby history, with Harper hitting nine home runs in the last 55 seconds to come back and win the title. Harper has said he doesn’t plan to do the competition again, which is a shame, as he could rise a lot higher on lists like this by doing so.
7. Todd Frazier
Before there was Harper, there was Frazier, the original hometown hero for winning the derby as a Red in Cincinnati in 2015. Frazier came back in all three rounds and hit the winner with his last swing of the bonus round. 2015 wasn’t Frazier’s lone derby experience, as he was runner-up in both 2014 and 2016. As such, he holds the distinction of having the most derby home runs of any contestant when you combine all his totals. He may only have one title to show for his three years, but that body of work made him a three-time finalist and one of the more accomplished derby contestants of the modern era.
6. Prince Fielder
Fielder’s violent, uppercut swing was a perfect match for the Home Run Derby, and it made him one of three contestants to win more than once. Fielder did so with two teams — in 2009, he claimed the title while a Milwaukee Brewer, and then won in 2012 while representing the Detroit Tigers. His prowess and enjoyment of the competition showed, as he participated six times over the course of his career. Fielder hit them impressively far, and his longevity in the competition is impressive.
5. Mark McGwire
McGwire only won once, as an Oakland Athletic in 1992, but was a 7-time participant whose most memorable derby likely came in 1999. McGwire repeatedly cleared the Green Monster at Fenway Park to the tune of 16 home runs, peppering the Mass Pike with moonshots in one of the most iconic derby performances ever. It hardly mattered that he ultimately lost after being eliminated by Jeromy Burnitz, of all people — McGwire’s first round at Fenway was unforgettable.
4. Ken Griffey Jr.
It was Griffey who turned the derby from a tape-delayed sideshow into an event all its own in the 1990s. In 1993, when ESPN first made the decision to air a taped version of the contest, Griffey hit the warehouse at Camden Yards. In 1998, the first year it was televised live, Griffey won at Coors Field, then repeated his feat a year later at Fenway Park, making him the only three-time champion. His backwards cap became an unmistakable part of his image. Even when he didn’t win, he was must-watch TV.
3. Giancarlo Stanton
Stanton was essentially born for the Home Run Derby, and it’s a wonder that he’s only won once. He has hit some breathtaking shots during his multiple appearances, and his 24 homers in 2016’s first round remains tied for second for the highest total in one round. That year, he won his lone derby by knocking off a formidable opponent in Todd Frazier. He did so by setting a derby record with 61 total homers despite hitting in notoriously hostile Petco Park. In its totality, it is one of the finest derby performances ever.
2. Aaron Judge
Judge left his mark on Marlins Park in 2017 not just because of the amount of home runs he hit, but because of how breathtaking they were. Judge won the competition after hitting several home runs over 500 feet, and even defied physics calculations by hitting the roof of the ballpark with a fly ball. Judge has refused to take part in other derbies since, which is unfortunate — he could be the most memorable contestant ever if he made himself a repeat participant.
1. Josh Hamilton
It’s worth remembering that Hamilton was still coming into his own in 2008, a redemption story as he battled back from drug and alcohol addiction. He was still in his first year with the Texas Rangers and had yet to win his MVP award. That made the 2008 Home Run Derby at Yankee Stadium in the stadium’s final year one of the great stories of the season. His 28 home runs in the first round is a record that still stands today despite the onset of a clock. Three of those home runs were estimated to go over 500 feet. He hit 13 straight at one point. It was the greatest show the Home Run Derby has ever produced, and remains the most-watched derby telecast ever. The combination of the player, the story behind how he got where he was, and the setting, made it a derby moment that will never be forgotten and won’t soon be replicated. He may not have won the actual event, but he won over sports fans with his memorable performance.
