Sports have played a very important role in the history of Chester; its one thing almost everyone can relate to. For athletic competition in Chester on the organized level, one would have to turn to the school systems and Chester High School.
As far as high school athletics are concerned, track and basketball were on the scene first, although Chester has always been known as a "football town."
1910 was the year Chester High School started scheduling out-of-town basketball teams, but had to play on outdoor courts. All traveling was done by train. In December 1921, students canvassed the city and collected $1,100 for completion of a new gymnasium, which was built behind the existing grade school - high school building on Market Street. The team, sometimes called the "Bluff City Boys", started the 1922 season with the juniors beating the seniors by the resounding score of 11 to 1.
Ed Thies' team of 1959-60 with Larry Costilow, Shelby Lawder, "Itch" Clendenin, Charlie Yankey, Ron Tindall, Bernie Kerkhover, Charlie Bullock, Bob Roth, Glen McGee, Dave Epstein and Gary Koch recorded CHS's best basketball record to date, 21-8, just missing a conference and regional title.
The Yellow Jacket team coached by Jim Hinkle made the slogan "Come Alive in '75" come true. The 1974-75 Chester Yellow Jackets captured the Chester Invitational Tournament title, and capped the season by winning the school's first regional tournament championship defeating highly rated Sparta 91-89 in overtime. The Yellow Jackets finished the season with an 18-11 record. Team members were Dan Ohlau, Mitch Eggemeyer, Paul Koeneman, "Buck" Johnson, Pat Mulholland, Mike Tindall, Mike Lutz, Brad Koeneman, Toby Search, Mike Schulte, Gary Bierman and Gary Bert.
Fans of Yellow Jacket basketball would have to wait until the 2012-2013 season for another regional championship. Playing in the Class 2A regional at Murphysboro, the Yellow Jackets defeated Trico 69-48 to win the school's second regional championship. Coached by Brad Norman, members of the team included Jake Lochhead, Kyle Landon, Chris Schwartz, Austin Gendron, Alec Weir, Link Cushman, Joel Clendenin, Reed Koeneman, Caleb Arbeiter, Boyd Miles, Joel Clendenin, Austin Redeker, Garrett Alms and Cody Mileur.
The present girls' gym at Chester High School was built in 1936 and later would be named "Marie Juergens' Gym" in honor of the long time women's PE teacher at Chester High School. The present Colbert Memorial Gym was named after school board member and school board president Daniel Colbert. Colbert Gym opened in 1963 and was remodeled in the summer of 1980 after a violent thunderstorm ripped the roof off.
Girls basketball didn't arrive on the scene until the 1979-80 season at Chester High School. It took the girls basketball program more than two season to secure that first eluvise win. After beginning with back to back 0-20 season, the Lady Yellow Jackets picked up their first win in the 1981-82 season under coach Don Flowers.
The Lady Yellow Jackets have won three regional championship (1985, 1986, 1992) in school history. The 1985-86 Chester Lady Yellow Jackets won 16 and lost 8 and were crowned Class A Regional Champions for the second year in a row. Co-captain Seniors Angie Brown and Jo Andrews led the way and were voted to the S.W.E. All Conference Team. The coach of the team were Bill Logan and Nikki Myers. Members were Jo Andrews, Rhonda Randolph, Jackie Jany, Charnelle McLean, Robin Weaver, Melissa Reiman, Amy Gray, Lisa Brown, Laura Wittenbrink, Kim Kueker, Angie Brown, and Ginger Yu.
Led by the dynamic duo of Jennifer and Jo Baldwin, the Lady Yellow Jackets won the regional championship in 1992. Chester defeated Belleville (Althoff) in the regional final at Waterloo High School. Other members of this team include Kathy Eggemeyer, Bria Rinehart, Jennifer Wingerter and Carrie Brown.
Track, at the high school, was actually the school's first sport, starting in 1909. Twelve athletes reported that year and were nicknamed "The Dirty Dozen." In 1958, Jim Colvis became the first Chester athlete to qualify for a state track meet. Jim returned to the state meet again in 1959. Chester has only one two conference championships in school history, coming in 1943 and 1946. The lone sectional championship came in the spring of 1998.
Girls track began at Chester High School in the spring of 1975 with Cathy Runge becoming the first girl to represent Chester at the state meeting in 1979. The girls track team has won 11 conference championships. The first came in 1992 in the final year of the Southwestern Egyptian Conference while the other six (1997, 2001, 2002, 2004, 2005, 2006) as a member of the Southern Illinois River to River's Mississippi Division. The next four have come as a member of the Black Diamond Conference (2011, 2012, 2013, 2014).
In the distance running sport of cross-country, in 1977, Terry Snider, became the first Yellow Jacket to qualify for the state finals. Since then, a handful of Yellow Jackets have represented the Orange and Black at the state finals. The Yellow Jackets have won three conference titles. The first came in 1979 as a member of the Southwestern Egyptian Conference and the other two came in 2010 and 2011 as a member of the Black Diamond Conference.
The Lady Yellow Jackets cross country team has won the conference title seven times. The first three (1999, 2004, 2005) as a member of the Southern Illinois River to River's Mississippi Division and the fourth came in the inaugural season (2010) as a member of the Black Diamond Conference. Additional titles in the BDC were recorded in 2011, 2012 and 2013.
Chester High School began a boys' golf program in the spring of 1972, under Coach Pat Malley. The Yellow Jackets won conference championships in 1973, 1974, 1975, spring of 1977, fall of 1977 when the state changed the sport from spring to fall and once again in 1978 under coach "Rocky" Bridges. During the first seven years of the program, Chester won six conference titles. Brad Koeneman was Chester's first state qualifier in boys' golf, happening in 1976.
Lady Yellow Jacket volleyball began in the 1974-75 school year. The Chester Lady Yellow Jacket volleyball team won their first regional championship in the fall of 1994. The coach that season was Kathy Albrecht. A second regional championship, under former head coach Jennifer (Cater) Rheinecker, was captured in 2008 as Chester defeated Elverado at the Steeleville Class 1A regional. Chester finished that season with a record of 13-20 after playing a mostly Class 2A schedule. The Lady Yellow Jackets have never captured a conference volleyball championship.
Lady Yellow Jacket softball also began in the 1974-75 school year. Just like volleyball, the Lady Jacket softball team has not captured a conference title nor have they won a regional championship. However, Chester has advanced to the regional championship a handful of times in the past seasons. Chester's best softball record came in the spring of 1992 as the River City ladies finished 15-8 under coach Jeff Kordys.
The baseball Yellow Jackets have won three conference titles, coming in 1976 as a member of the Southwestern Egyptian Conference and in 1999 as a member of the Mississippi Division of the Southern Illinois River to River. The Yellow Jackets have claimed three district titles (1949, 1950 and 1967) and two regional championships (1999 and 2002). The 1999 record of 28-3 is the best in school history. That year, Chester came within three outs of advancing to the state finals but lost the sectional final to Nashville at the Marissa Sectional.
As a member of the Black Diamond Conference, the Yellow Jackets claimed a share of the championship in 2012 and 2013. But during the 2014 season, the Yellow Jackets finished conference play with a record of 10-0 and won the IHSA Regional Championship by beating Du Quoin 4-3 in the championship game.
Through the years, Chester has produced several professional baseball players, most being pitchers. Bill Braun was the first, signing in 1925 and playing in the New York Giants' farm system as a third baseman. Roger Wolff was the most successful, being signed by Branch Rickey of the St. Louis Cardinals in 1939. "Rog" played in the majors from 1941 through 1947, winning 20 games for Washington in 1945. Erwin Schueren signed a pro contract with the St. Louis Cardinals in 1936 and played a season and a half in the minors. Charlie Klindworth also played minor league ball, 1949-50, signing with the St. Louis Browns. Harold Lawder was another in 1949. In 1952, Bill Wingerter signed with the Cleveland Indians, and played in the Florida league. Two other Chesterites to play pro ball were Leonard "Itch" Clendenin and brother Carter. Both signed with the Phillies in 1961. Carter got out in 1962 but "Itch" played in the Phils farm system for six years. Leonard wasn't a bad hitter either, winning the conference batting title his senior year in high school, with a .500 average.
Probably, Chester High School's favorite sport, bother participant-wise and spectator-wise is football. 17 players were on the squad when Chester inaugurated its football program on September 13, 1923. The schools' principal, E.S. Brown, was the coach. A football field was marked off on the fairgrounds baseball diamond in the Fairview Addition where Washington and Lincoln Boulevards are located now. There were no seats for the fans and the dressing rooms and shower facilities were at the grade school building on Market Street. The players would dress, run along the cobblestone streets to the football field, practice or play and then run back to the dressing rooms. That year, Chester played two games each with Gorham, Perryville and Farmington. The present football field, W.O. Smith Field, was built around 1935 and was lighted in 1946. The field was named after longtime teacher, coach and friend of the Yellow Jackets, W.O. Smith.
The first outstanding football season recorded by the Yellow Jackets was in 1938 as the Jackets, under Coach Bill Weber, defeated Murphysboro 18-7, with the season's only loss coming at the hands of Pinckneyville 18-13. Chester finished up 7-1. Some of that team's players were Joe and Dale Bruegger, Al Magers, John Heuer, George and Dale Allison and John Clayton.
In 1939, Chester joined the newly formed Western Egyptian Conference and almost came away with the leagues' first title. Chester tied Murphy 6-6 but was defeated by Du Quoin 20-19, finishing the season with an 8-1-1 record.
Bill Brewer and W.O. Smith were the coaches in 1953 when the Chester Yellow Jackets were conference co-champs with Murphysboro, although the Jackets defeated Murphy 18-0. A tough 7-6 early season loss to Anna cost Chester a clean title. The conference mark in 1953 was 6-1. The 1954 Bill Brewer team produced the same results as the previous year, a conference co-championship. Chester did not lose a conference game that year, but played to a scoreless tie with Murphysboro.
Some members of the 1953 and 1954 football teams included Bob Kendrick, Roger Kattenbraker, Gary Frazer, Glen Blum, Don Daschka, Dick Decker, John Uffelman, Carrol Eggemeyer, Bob Claussen, Jim Hardy, John Birchle, Bill Juergens, Wayne Zimmer, "Jigs" O'Connor, Dale Usher, Ned Carlton, Marvin Eggemeyer, Harold Meisenheimer, Wayne Ahrers, Melvin Runger, Ray Fricke, Dave Phelps, Tom Cress, Bob Parker, Bob Tindall, Charlie Higgins, Tom Klein, Paul Crisler, Mike Hathaway, Larry Lipe, Don Misselhorn, Bill Jeremiah and Neal Mangold.
The long-awaited conference championship came in 1965, when the Yellow Jackets recorded the school's first unbeaten and untied conference mark, winning the title by beating Murphysboro 7-0. First year coach Jerry Germain, assisted by W.O. Smith, who coached at Chester High School for 25 years, directed his squad to an 8-1 overall mark, losing only a non-conference game to Valle Catholic in nearby Ste. Genevieve, MO.
Only one loss marred Chester's conference slate in 1966, a 14-12 decision to Murphysboro. 1966 was highlighted by the naming of Mark Colvis to the all-state team.
Head football coach John Trapp, probably recorded the school's best coaching mark in football, as he directed the Yellow Jackets in 1977 and 1978, finishing both years with identical 8-1 records, losing only to Chester's old football menaces - Murphysboro.
Chester's first playoff birth came in the 1996 season when Coach Dennis Roth's team was an at-large selection to the Class 2A playoffs. Chester lost that game 49-8 at Tuscola but would return to the playoffs the next year. As a guest of state-ranked Breese Mater Dei, a CHS team led by Micah Reiman and Scott Lamb, shocked the host Knights 35-21 in the opening round of the Class 3A playoffs. The following week, Chester hosted the first football playoff game in school history but lost 30-7 to the Benton Rangers.
One of the top seasons in the history of Yellow Jacket football came in the fall of 1999. The Yellow Jackets finished the season with a record of 8-2 and lost both games by a combined total of two points. It was that season that many will remember "The Drive" when the Yellow Jackets rallied from a 13-0 halftime deficit and beat Du Quoin 14-13 at W.O. Smith Field.
Although Chester never captured an outright conference championship while a member of the Southern Illinois River to River's Mississippi Division, the smallest school in the division did share the conference championship in 1999, 2000 and 2001.
Since the first playoff appearance, Chester has returned to the playoffs ten additional times (1997, 1999, 2000, 2001, 2002, 2006, 2008, 2009, 2012), the latest coming under current head coach Bryan Lee in 2013.
Beginning in the fall of 2010, Chester left the SIRR for the Black Diamond Conference, changing places with Carterville who was a charter member of the BDC.
In the fall of 2012, the Yellow Jackets won their first outright conference championship since 1965. As a member of the Black Diamond Conference, Chester finished the regular season with a record of 9-0. The first undefeated football season in the long, storied history of Yellow Jacket football.