Cape Cod’s Annual Home Run Derby: Always a Hit

Orleans’ Frank Thomas won the very first Cape Cod Baseball Home Run Derby in 1988, and did so using his Auburn teammate Bo Jackson’s bat. (Courtesy of Cape Cod Baseball League)

 

One of the highlights of every Cape Cod Baseball League season is its annual home-run derby. Home-run derbies have a long history. For years, many baseball games featured informal hitting contests as added attractions. Having the mighty Babe Ruth or other slugger show hitting prowess was a way to induce fans to come out early to the game. Teams and leagues have realized that batting practice power is something every fan can appreciate. Home run competitions have been a persistent part of the game.

Major League Baseball decided that the time was right to finally introduce its own home-run derby officially in 1985. It took place at Minneapolis’s Metrodome before the 1985 All-Star Game. The competition was immediately popular. The majors’ first winners of the revived home-run derby included Dave Parker, Darryl Strawberry, Wally Joyner, and Andre Dawson.1

Home-run derbies were part of the growth and proliferation of televised baseball. A popular syndicated show in 1959, Home Run Derby featured the batting skills of luminaries like Willie Mays, Duke Snider, and Hank Aaron.2 The show lasted only a year. But the growth of cable television and ESPN in the 1980s created demand for alternative sports programming. The old black-and-white episodes from the original show were rescued from the producers’ archives and re-aired.

In 1988, the Cape Cod Baseball League Board of Directors chose to launch its own version of the event. The annual Cape Cod competition gave scouts and fans an opportunity to see how baseball’s next generation of home-run kings adjusted to the use of wooden bats on the Cape. League fans have not been disappointed.

It’s difficult to pinpoint the most outstanding home-run derby performances over the years but there are a few that stand out. Written accounts of home-run competitions aren’t detailed but the first competition, held in 1988, must have made a strong impression.

The field of competitors was very strong. Future Hall of Famer Frank Thomas, representing Orleans, and Jeff Bagwell from Chatham were the headliners. But future major leaguers Eric Wedge, Mo Vaughn, and Chuck Knoblauch were also contestants.3

The first derby took place at Eldredge Park in Orleans, a ballpark that favors strong right-handed pull hitters. “It was barely 300 feet down the line in left field and something like 330 feet to right,” said Bob St. Pierre, a longtime volunteer of the Wareham Gatemen, who was present at the event.4

 

 

The Cape’s annual home-run derby has served as an indispensable part of Cape League baseball.

Another legendary competition occurred when former Colorado Rockies first baseman Todd Helton won it in 1994. An outstanding hitter and quarterback at the University of Tennessee, Helton did not hit a single home-run during his year on the Cape, yet was entered into the exhibition.

How Helton was picked is controversial. He was chosen along with such players as Sean Casey, future number-one pick Darin Erstad, longtime outfielder Mark Kotsay – who was the MVP of the College World Series – and emerging power threat Mike Glavine from Northeastern University in Boston, who hit 13 homers on the Cape.7

But how Helton won is mysterious. Glavine, one of the Cape’s hottest hitters, and Erstad hit balls that would normally be home runs in the derby but died in the wind. Helton, normally an opposite-field hitter, out of character pulled the ball.8

“What was strange,” said Helton, “is that I normally didn’t hit balls out to center and right.”9

Bill Mosiello, Helton’s coach at Tennessee who also coached Brewster, witnessed Helton’s performance. Mosiello observed that Helton “just hit bullets out there that day, and they cut through the wind.”10

The derby generally takes place an hour or two before the annual all-star game on the Cape. The competition has taken place before all-star games that have been held around the Cape and, from 2009-2011, at Fenway Park.

Former Chatham Angler and future Tampa Bay Ray Richie Shaffer had a memorable 2011 derby at his first visit to Fenway Park.

The big right-hander started off slowly and had five quick outs. But once Shaffer got comfortable, he easily launched balls over the Green Monster. “I was overswinging a little bit and I was a little tense and nervous, but once I got the first one out I kind of relaxed and got into a groove,” said Shaffer.

Shaffer’s momentum continued to increase with each succeeding home run. Consecutive home runs were progressively launched higher and farther. After his first three home runs landed in the Monster seats, Shaffer’s fourth left the crowd in awe. The ball was launched halfway up the left-field light tower. On his last home run, Shaffer put an exclamation point on his awesome performance with a homer that was crushed over the “Sports Authority” sign outside the ballpark.11

Shaffer appreciated the opportunity to hit home runs in one of the most historic ballparks in America. “It was pretty awesome,” he said. “Fenway is one of those iconic parks that I dreamed to play in as a kid. To get the chance to hit there it was amazing and it was something that I have dreamed about for a long time.”12

 

 

There are lots of interesting and unique facts about the competition.

Previous winners of the home-run derby have come from every team. Orleans leads in winners. The only player who has won both the major-league and Cape Cod League derby is Frank Thomas. Former Wareham Gatemen Matt and Luke Murton are the only brothers to win the competition. Matt was the winner in 2002 and Luke won five years later. Todd Hoilman, representing Cotuit, is the only player to win both home-run derbies at the College World Series and the Cape. Only one player, Yarmouth-Dennis’s Todd Greene, is the sole slugger to win the home-run derby and lead the league in homers.13

A strange but true fact is that some of baseball’s greatest sluggers have not been able to win the Cape League’s home-run derby.

Todd Frazier won the major-league home-run derby in 2015 and was runner-up in 2014 and 2016 but missed out in qualifying for the Cape Cod Baseball League contest in both years that he played for Chatham, 2005 and 2006.

Aaron Judge spent the summer of 2012 in Brewster but did not win the derby. That year, two home-run derbies were actually held. At “Cape Cod Day at Fenway,” the winner was Judge’s teammate, Dylan Davis, a versatile relief pitcher-outfielder from Oregon State.14 A highlight of the 2012 contest at Fenway Park was Davis’s tape-measure blast that landed on Lansdowne Street.15 As of 2025, Davis was out of baseball after a long career in the Giants farm system while Judge, a sure-thing first ballot future member of the Baseball Hall of Fame, patrols the outfield for the New York Yankees.

The Phillies’ Kyle Schwarber is another slugger who played on the Cape but did not win the home-run derby. With a lifetime batting average of .343 with 8 home runs, 10 doubles, and 38 RBIs, Schwarber earned a place in the Cape Cod Baseball League’s Hall of Fame as the MVP of Wareham’s 2012 championship team. Instead, former Giants farmhand Tyler Horan, a native of nearby Middleboro, Massachusetts, and a Virginia Tech grad, represented the Gatemen in the home-run derby and set the modern home-run record on the Cape with 16 home runs.16

Schwarber, who played two years with the Gatemen, would have surely been picked to participate in the 2013 competition but couldn’t be because he was picked for the United States National team. The Indiana University product, who in recent years has been the designated hitter for the Phillies, came back to help his Cape Cod teammates try to help Wareham defend its championship.17

Seattle Mariner and home-run-hitting slugger Cal Raleigh, a Harwich Mariner in the summer of 2016, apparently had some trouble adjusting to wood bats. Not only did Raleigh miss out on being selected for the home-run derby but he was not selected for the all-star team. He hit only one home run with a batting average of .204.18 Nine years later, in 2025, Raleigh, who was drafted in the third round of the major-league draft, hit 60 home runs as the American League home-run champion.

THOMAS MASON is a recovering attorney and sometime journalist from Lakeville, Massachusetts. Tom has worked as a contributing writer for the New Bedford Standard-Times. Stories he has written have appeared in the Cape Cod Times, Fall River Herald News, the Taunton Gazette, the Quincy Patriot Ledger, and in many other publications in the New England region. Tom has worked as a writer for yearbooks of the Brockton Rox and the Pawtucket Red Sox. His book, Maple Street Press Guide to New England Ballparks: From Maine to Fenway to the Cape and Everything in Between, featured the Cape Cod Baseball League. Tom was thrilled when, a number of years ago, he was asked to throw out the first pitch of the Cape Cod League playoffs.

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Cape Cod Baseball League Home Run Derby Champions 1988-2025

• 1988: Frank Thomas, Orleans
• 1989: Mike Thomas, Orleans
• 1990: Mike Gropusso, Orleans
• 1991: Chad McConnell, Hyannis
• 1992: Todd Greene, Yarmouth-Dennis
• 1993: Scott Krause, Cotuit
• 1994: Todd Helton, Orleans
• 1995: Dan Olson, Hyannis
• 1996: Eddy Furniss, Y-D
• 1997: John Scheschuk, Cotuit
• 1998: Matt Cepicky, Chatham
• 1999: Doc Brooks, Falmouth
• 2000: Jason Cooper, Y-D
• 2001: Jason Cooper, Y-D
• 2002: Matt Murton, Wareham
• 2003: Cesar Nicolas, Orleans
• 2004: Austin Easley, Bourne
• 2005: Aaron Bates, Brewster
• 2006: Mitch Moreland, Bourne
• 2007: Luke Murton, Wareham
• 2008: Angelo Songco, Orleans
• 2009: Connor Powers, Harwich
• 2010: Paul Hollman, Cotuit
• 2011: Richie Shaffer, Chatham
• 2012: Jacoby Jones, Harwich
• 2013: Skyler Ewing, Hyannis
• 2014: Sal Annuziata, Harwich
• 2015: Logan Sowers, Wareham
• 2016: Kameron Esthay, Hyannis
• 2017: Stephen Scott, Orleans
• 2018: Spencer Torkelson, Chatham
• 2019: Tyler Hardman, Brewster
• 2020: No All-Star Game – COVID shutdown
• 2021: No All-Star Game – COVID shutdown
• 2022: Lyle Miller-Green, Chatham
• 2023: James Tibbs, Brewster
• 2024: Ethan Petry, Y-D
• 2025: Kuhio Aloy, Bourne

 

SOURCES

In addition to the sources cited in the Notes, the author consulted baseball-reference.com , capecodtimes.com , and capecodleague.com . The author also used youtube.com , where he was able to relive some of the derbies of the past. The author also used the following resource:

Mason, Tom, Mark A. Brown, and David Laurila. Maple Street Press Guide to New England Ballparks: From Maine to Fenway to the Cape and Everything in Between (Hingham, Massachusetts: Maple Street Press, 2007).

 

ACKNOWLEDGMENTS

The author acknowledges and thanks Mike Richard, historian of the Cape Cod League, for helping him put together this article. There is very little written information, besides the winners and participants of previous derbies, and this article could not have been done without his help.

 

NOTES

1 Chad Thornberg, “Derby History: Looking Back at Past Slugfests,” MLB.com , July 14, 2025, www.mlb.com/news/home-run-derby-history-c283844278 .

2 Don Zminda, “Home-Run Derby: A Tale of Baseball and Hollywood,” The National Pastime: Endless Seasons: Baseball in Southern California (Phoenix: SABR, 2011). sabr.org/journal/article/home-run-derby-a-tale-of-baseball-and-hollywood/ .

3 Bill Whelan, “Frank Thomas: From Cape Cod to Cooperstown,” Wareham Week, January 21, 2014. Accessed September 8, 2024, https://wareham.theweektoday.com/article/frank-thomas-cape-cod-cooperstown/12807 .

4 Whelan.

5 Mike Richard, email to author on January 8, 2026.

6 Whelan, “Frank Thomas.”

7 Peter Gammons, “Gammons: Todd Helton’s Hall of Fame Case Is Complicated, but His Career Shouldn’t Be Ignored,” The Athletic, January 24, 2022, www.nytimes.com/athletic/3041845/2022/01/24/gammons-todd-heltons-hall-of-fame-case-is-complicated-but-his-career-shouldnt-be-ignored/ .

8 Gammons.

9 Gammons.

10 Gammons.

11 “Shaffer Wins CCBL Home-Run Derby,” Cape Cod Baseball League, August 2, 2011, ism3.infinityprosports.com/ismdata/2012030201/std-sitebuilder/sites/201801/www/en/news/index.html?article_id=960 .

12 “Shaffer Wins CCBL Home-run Derby.”

13 Mike Richard, email to author on August 13, 2025.

14 “Dylan Davis – Baseball,” Oregon State University Athletics, osubeavers.com/sports/baseball/roster/davis-dylan/3207 . Accessed January 6, 2026.

15 CCBL Public Relations Office,” Cape Cod Day at Fenway – Hood Home-Run Derby Is Highlight,” https://ism3.infinityprosports.com/ismdata/2012030201/std-sitebuilder/sites/201201/www/en/news/season/index.html?article_id=1413 .

16 “Middleboro’s Tyler Horan Earns Spot in Cape Cod Baseball League Hall of Fame,” Brockton (Massachusetts) Enterprise, June 24, 2020, www.enterprisenews.com/story/sports/college/2020/06/24/middleboros-tyler-horan-earns-spot-in-cape-cod-baseball-league-hall-of-fame/114512028/ .

17 Will Geoghegan, “MVP Return,” Right Field Fog.com, July 26, 2013, https://www.rightfieldfog.com/?p=3010

18 Daniel Kramer, “‘We Were All Wrong about Cal Raleigh’: How the Mariners Found Their Star Catcher,” MLB.com, October 1, 2025, www.mlb.com/news/the-scouting-of-the-mariners-cal-raleigh .