Chicago Cubs: A history of notable Home Run Derby performances

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Here are the best Home Run Derby performances by a Chicago Cubs player.

All-Star Weekend in Major League Baseball brings an air of excitement and innocence to players and fans alike. The derby would have entered its 35th year a part of the festivities a staple of all-star weekend. Unfortunately, the novel coronavirus has halted our world, for the time being.

For the Chicago Cubs, many of their star hitters stepped up to the plate in an attempt to be crowned the home run king. In 1987 it was Andre Dawson. Ryne Sandberg, in 1990, the year I was born, ironically. Sammy Sosa found his success in the early 2000s.

The derby represents a child-like nostalgia for grown men. It represents summer. It represents freedom. For fans, it gives them their own true fireworks, watching behemoths mash baseballs into orbit. Cubs fans can reminisce about each performance from each decade to look back at who represented best.

(Photo by: Bernstein Associates/Getty Images) /

Chicago Cubs: 1987 – Andre Dawson defeats Ozzie Virgil

The winter of 1987 saw Dawson sign a one-year deal with the Cubs for a mere $650,000. Outside of Chicago’s frivolity, it became a contract that would change the course of how money moved hands and arbitration would play an essential role in future contracts.

By season’s end, Dawson had smashed 49 long balls for the Cubs. Rewinding to the Midsummer Classic weekend, he was chosen as one of four players to participate in the then third annual Home Run Derby.

In the first few years of the derby itself, there was a lot of experimentation. Trying to figure out the best model for the entertainment, in 1987, there existed two “innings” or, more simply, rounds. Each of the participants received five outs per “inning.”

Unfortunately, it will go down as one of the most blasé derbies in MLB history. A total of eight home runs were hit—Dawson, who won the whole thing, hit four bombs. Virgil finished second with two, and both George Bell and Mark McGwire each ended the mundane event with a single home run. Still, Dawson became the first official Cub to win a derby, so he finds himself atop this list.

(Photo by Ronald C. Modra/Getty Images) /

Chicago Cubs: 1990 – Ryne Sandberg defeats Mark McGwire, Matt Williams

In the Chinese Zodiac, the year 1990, coincidentally the same year I was born, is known as the “Year of the Horse.” Well, if you’re a Cubs fan, you may remember it slightly differently. Sandberg set career highs in many areas as it was a year to remember for “Ryno.”

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Sandberg mashed 40 home runs while simultaneously driving in 100 runs and swiping 25 bags. He finished the year with a .306 average, striking out at just a 12.4 percent rate, and posting a 142 wRC+.

The All-Star Game was held at Wrigley Field in 1990. Hall of Famer and Cubs ‘GOAT’ Ernie Banks threw out the ceremonial first pitch. Sandberg represented the hometown team in the derby, with other big names trying to stake their claim as the home run king.

Similar to the derby of 1987, there were very few home runs hit. Only five balls flew over the wall that day, with many guys failing to hit at least one. Five of the eight players dropped goose eggs. Sandberg defeated Mark McGwire and Matt Williams and legendary Cubs fan and face Bill Murray emceed the fun. Despite the lack of long balls, it was a fun day to remember in Wrigley.

Chicago Cubs: Sosa Y2K’s his way to victory

I remember sitting in the gymnasium of my elementary school as a 10-year-old waiting for an assembly to begin. If my memory serves me correctly, a Tae-Kwon-Do school from the area was coming to perform a demonstration. A couple of minutes before it was about to start, the power went out, and, my friend, who was sitting next to me yelled out for the entire school to hear, “Y2K!”

The year 2000 was a transformative experience in many people’s eyes. It was also the year Sammy Sosa took home his first derby crown. Sosa was well into his Cubs career by 2000. He came into the all-star break, having smashed 23 home runs with a 140 OPS+.

Sosa breezed his way through the competition, which set up a championship round with back-to-back winner Ken Griffey Jr. Sitting on five outs to play, Sosa launched a shot into left field, which got Chris Berman yelling about the moon and lunar eclipses. A couple of balls later, Sosa launched to near dead center field, onto the concourse.

Seemingly tiring out, with two outs left to play with, Sosa once again sent Berman into a tizzy, this time with an upper deck shot landing in the very back rows. He would finish with nine home runs in the final round, which was good enough to land Sosa his first derby crown.

(Photo by Brace Hemmelgarn/Minnesota Twins/Getty Images) /

Chicago Cubs: Kris Bryant, Anthony Rizzo do damage

The 2015 season will always be remembered as the year it began, in Wrigleyville. Highly touted draft prospect Kris Bryant was a rookie, and team captain Anthony Rizzo was a few years into his Cubs tenure. Each guy earned all-star nods as reserves, and each took part in the Home Run Derby.

Bryant and Rizzo each posted double-digit home run totals in the first half of 2015. Bryant came out of the gate riding the struggle bus, but, turned it around and entered the break with 12 big flies. Rizzo, meanwhile, posted a solid first half with a .298 average and 16 home runs.

In what debuted as the newest format for the yearly competition, Rizzo was the first to experience a running clock’s change. He finished with eight in the first round, losing narrowly to Josh Donaldson, who hit nine. Bryant squared off against Albert Pujols, which drew the crowd to a pause. Tied 9-9 as time ran down, Pujols stepped into the box and delivered the first “buzzer-beating” home run in MLB history to take down Bryant.

Although the final results did not bounce Bryant and Rizzo’s way, it was still notable as it was the beginning of a special time for the Cubs and a glimpse into the future with ‘KB’ and the thrills he was about to bring to the city of Chicago.

Chicago Cubs: A night to remember

The 2018 Home Run Derby had to play out as it did with the hometown golden boy Bryce Harper representing the weekend hosts in our nation’s capital. Despite a furious finish, which eventually saw Harper crowned as king, Kyle Schwarber put up his own impressive performance and nearly owned the night.

It is no secret that Schwarber can hit the leather off of a baseball. Nor is it a secret that he can hit a ball clear out of a stadium. Coming into the all-star weekend, Schwarber had clubbed 18 home runs, which made him a prime candidate to compete.

Teammate Javier Baez can also be included in this spot. While Baez experienced an early exit, he did notably hit the longest home run of the night: a 479-foot moonshot. Schwarber advanced to the final round to face Harper.

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In a more than concerted effort to win it all, Schwarber drove 18 balls into the dark D.C. sky. Unfortunately, it would not be enough as Harper narrowly surpassed Schwarber within the final minute to be crowned the champion. Despite the heroics from Harper, Schwarber is probably talked about more regarding his finals performance as it remains tantamount to none before.

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