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After retiring from the NFL, Holecek returned to Illinois to work in finance and assist coaching high school football at St. Ignatius in Chicago. At the insistence of Nick Rassas (NFL safety, Notre Dame All-American, and Loyola Academy graduate) Holecek applied for the head coach position at Loyola Academy, a private college preparatory in Wilmette, Illinois. NFL coaches Marv Levy and Wade Phillips called the school's AD Pat Mahoney on Holecek's behalf. Mahoney remembered “You could see that he was a teacher of the game... He was smart and driven. He wasn’t going to do anything half-heartedly.” Holecek is Loyola's head varsity football coach and as the assistant athletic director.

Holecek's teams have won at least 11 games for the last nine consecutive years (as of 2018). Loyola plays in the Chicago Catholic League Blue division. Loyola has won outright or shared six of the last eight CCLB conference titles (as of 2018). Holecek's career coaching record is 146–30 with an 83% overall winning percentage; including over 91% of games in the last four full seasons (2015-2018). Holecek's Ramblers are 18–2 in the state playoffs over the last four years, winning two State Championships.

In November 2018, Loyola Academy beat their first three playoff opponents, including two shutouts, and qualified for their ninth IHSA 8A semifinals in the last ten years. Loyola went on to beat Brother Rice 13–3 in the 8A final game on November 24, 2018. Underdogs Loyola beat the 14th, 6th (10-1 Maine South), 3rd (undefeated Oswego), 2nd (12-0 and reigning 8a champion Lincoln Way East) and 1st seeds (13-0 Brother Rice) during their playoff run. Holecek said. “They fulfilled something I will always remember, one of the most special seasons of my life. Nothing is going to beat this in my career."

In November 2018, Holecek was awarded 22nd Century Media's 2018 Football Coach of the Year.

USA Today 'Coach of the Year' for the ALL-USA Illinois Football Team in December 2018.

Loyola finished the regular 2016 season 9-0 as the Ramblers (#1 ranked team in Illinois) defeated #2 ranked Mount Carmel early in the season and #3 ranked Brother Rice to close the season (both games were on the road). Loyola players were paid a visit by NFL legend Marv Levy prior to the beginning the 2016 8A IHSA playoffs (#1 seed). At the end of October, Holecek's Ramblers ranked #5 nationally (USA Today Super 25 Computer Rankings) and had a 26-game win streak, plus had a 24-game home field winning streak that dates back to 2012. LA finished as runner-up in 2016 in class 8A.

In January 2016, Holecek was named one of six finalists for the 2016 U.S. Army All-American Bowl National Coach of the Year award. The award honors the nation's top high school football coach for exceptional coaching abilities and leadership skills, as well as acknowledging his role as a positive influence to young Americans on and off the field.

In late September 2015, John Holecek notched his 100th coaching victory—becoming the first Illinois high school football coach to reach 100 wins in so short of a career span (9 1/2 seasons). At the close of the regular season in October 2015, Loyola ranked number 1 in the state of Illinois in all major football polls after completing a 9-0 undefeated regular season, by way of a 34-point average margin of victory (24-point lowest margin of victory). Holecek told the Chicago Tribune, "We haven't thrown one ball in the fourth quarter". Loyola won the 2015 Chicago Catholic League Blue conference title after a 49–21 victory over defending 7A State Champion Mt. Carmel.

In November 2015, Loyola won their first four playoff games to go to 13–0, including a dominating (early third quarter running clock) victory over the defending 8A champion Stevenson 49–0, a come-from-behind victory over Homewood Flossmor (who was rated #1 in the state for the first eight weeks of the season) in a televised game attended by over 6,000 fans, and a close semi-final victory over Palatine in the snow. Loyola Academy ranked in the top 20 nationally by Maxpreps Experts, Freeman, and USA Today and number 6 nationally in the USA Today Super 25 Computer Rankings. On November 28, 2015, Loyola played Marist for the state title and utilized an aggressive defensive scheme with many blitz packages. LA defeated Marist 41–0 (with a running clock imposed) to win the IHSA class 8A State Championship, extending its season record to 14–0. For the 2015 season LA outscored its opponents 558–123, won nine games by 30 points or more, and had six shut-outs.

Presented the Ray Meyer Coach Award in 2015 at the Giant Awards — the former Chicago Park District superintendent Ed Kelly's sports program that honors accomplished Chicagoans in various fields.

In April 2014, Holecek's coaching mentor Marv Levy visited Loyola as part of the NFL "Heart of a Hall of Famer" program. Levy's lessons were laced with words like “perseverance”, “work ethic”, and “preparation”, hallmarks of Holecek's playing career and coaching tenure at Loyola.

Loyola Academy won the Chicago Prep Bowl 14-7 over Chicago Curie at Soldier Field on November 28, 2014. Playing not the road with their third-string QB, LA had previously lost a close state playoff game against the eventual state champions.

In August 2014, the Butkus Foundation honored Holecek at a Chicago Bears game for his work has a Chicago youth sports leader.

Loyola was the 8A state championship runner-up in 2013, after losing to Naperville Central 13–10 in the title game.

Loyola finished the regular season at 8–1 in 2017 and the Ramblers’ won their third consecutive undefeated and outright Catholic Blue League title in a row (with Holecek again receiving Coach of the Year awards). LA's home win streak stood at 29 games (including a victory against perennial Californian powerhouse Bishop Amat) as the playoffs began. In early Nov 2017, Holecek became the school's all-time coaching leader with 133 wins - including the last ten in a row and 31 consecutive victories at home.</https://www.journal-topics.com/articles/ramblers-brush-aside-red-devils/>

In August 2012, Holecek brought his Ramblers to Dublin, Ireland to play Jesuit Dallas in Global Ireland Football Tournament 2012, featuring Notre Dame vs Navy as the main draw. That same year John Holecek joined Dick Butkus in making an instructional video one of one Butkus's websites to emphasize tackling with proper form to reduce the risk of head injury. Loyola was a state semi-finalist in 2012.

In 2011, he coached the Ramblers to a second-place finish in the Class 8A State Championship, losing to Bolingbrook High School 21–17 in inclement weather. This was only the school's third appearance in the state championship game and the first in 18 years.

In September 2011, Holecek was inducted into the Chicago Sports Hall-of-Fame. Holecek received accolades for his grit and determination and for dealing with adversity by successfully rehabbing three major knee injuries. Other inductees included Jim Calhoun, Bobby Hull, Glenn Doc Rivers, Barry Sanders and former Notre Dame and Pittsburgh Steelers running back Rocky Bleier.

Also that month, LA was honored with the 11th Annual MaxPreps "Tour of Champions" award presented by the Army National Guard. The award honors select state champions who are also national ranked according to MaxPreps national computer rankings.

The 2009 team played in the state semi-finals. The 2010 team was the start of Holecek's run on Chicago Catholic League Blue championships.

In 2008, he coached Loyola to a Prep Bowl Championship at Soldier Field as the L.A. Ramblers defeated Lane Tech, 17–0.

Since taking the reins in 2006, Holecek's teams have been to the playoffs every year, including nine the last ten Illinois State 8A Semi-Finals or Finals and the four consecutive Illinois State 8A Finals since 2018.

Holecek then signed with the Atlanta Falcons in his 8th season (2002). Holecek was reunited with Falcon defensive coordinator Wade Phillips, who tutored Holecek for six seasons while serving as defensive coordinator or head coach of the Buffalo Bills. Holecek started the first 11 games for the play-off bound Falcons and was the team's second leading tackler before breaking his upper wrist/forearm. Holecek seriously re-injured his right arm late and knee and the resulting surgery was career ending.

Holecek played both tight end and middle linebacker for Marian coach Dave Mattio. Coach Mattio reflected on Holecek in a 2001 Times newspaper interview, "Most people don't know he was a good catcher and could have been a great wrestler," Mattio said. "Even then, I saw how he never quit and everything had to be perfect. He was a tough kid, I compare him to street kid because of his toughness and being hard-nosed on the field. He played hard and the thing about John, he could run for a big guy".

Holecek had his NFL jersey number 52 retired by his alma mater in 2000. Other retired Marian jerseys include Mike Prior and high school and one-season NFL teammate Rodney Harrison (San Diego Chargers).

His finest campaign came in 2000 when he started all 16 games and had a career-high 165 combined tackles. He also intercepted one pass and deflected four others.

In his seventh season, Holecek was released very late in training camp in salary cap move by a new Bills head coach and GM. Holecek was quickly signed by the San Diego Chargers. The Bills who ranked 3rd in total defense in the league in 2000, finished 3-13 without Holecek and others in 2001. John played in San Diego for one partial season; he finished the last five games of the season on injured reserve as a knee problems limited him to just 11 injury-riddled appearances.

In 1999 Holecek tallied 116 combined tackles, including 63 unassisted, to go along with one sack, one interception, six passes defensed and two forced fumbles. Holecek's remarkable season also included a career-best 22-tackle outing in a Wild Card Playoff game played at Tennessee.

NFL Defensive Player of the Week, for a stellar Monday Night Football game vs the Miami Dolphins in October 1999. Holecek first registered a jarring sack on Dan Marino that led to Gabe Northern's fumble return for a touchdown, then with Buffalo clinging to a 23–18 lead late, Holecek registered his first career interception. Facing a three-receiver set, Holecek dropped back in zone defense, and picked off Dan Marino. Holecek said "obviously, with Dan Marino, it's a special play."

In 1998 Holecek led the Bills with 133 tackles in his first season as a full-time starter and was named the team's recipient of the Ed Block Courage Award. Holecek was credited with a career game high of 21 tackles during game film review of the Miami Dolphins Wild Card playoff game. That season the Bills improved to the fifth-rated run defense in the NFL—up from 15th the year before.

NFL Ed Block Courage Award in 1998. Award presented to a player who personifies courage, strength, leadership and pursuit of excellence.

Holecek was drafted in 1995 by the Buffalo Bills in the fifth round if the NFL draft (144th pick) of the 1995 draft. Holecek was drafted by Pro Football Hall of Fame coach Marv Levy. Holecek also played for NFL coach Wade Phillips.

Holecek reported to the perennial Super Bowl bound Bills rookie camp in April 1995. He played six seasons with the Bills, averaging over 14 starts his last three seasons. Holecek flourished as an inside linebacker in Phillips' defensive 3-4 system. He also briefly played middle linebacker in a 4-3 alignment when injuries caused Coach Phillips to switch defenses mid-season. John emerged as a defensive stalwart and on-field coach for the Bills, notching an incredible 414 tackles from 1998-2000 and became known for his technique and football acumen.

Holecek started eight games over the course of his first three seasons with the Bills (1995-1998). After playing in only one game his rookie season due to injury, Holecek was ready to be a regular contributor to the team in 1996 before another knee injury suffered in the first preseason game forced him to spend the entire year on injured reserve. Holecek also pursued completion of his MBA degree these seasons. In 1997 Holecek provided the first glimpse of his promising future as he recorded 86 combined tackles in eight starts (14 appearances). Head coach Marc Levy stated decades later that Holecek was one of his favorite NFL players to coach.

University of Illinois, Bruce Capel Award as the team's "Most Courageous Player" in 1994.

After graduation from Marian Catholic High School (Illinois), John played for the Illinois Fighting Illini football team from 1990 to 1994. Holecek was the Illini's co-Defensive Player of the Year in his red-shirt freshman season. Holecek made the All-Big in 1993 and 1994 teams, and was also a team captain. Holecek suffered multiple ACL injuries during his Illinois career, dampening prior Butkus Award consideration.

Holecek was part of the linebacker foursome that gave Illinois the nickname "Linebacker U" in the 1990s. The Foursome also featured All-American and first-round, second and third overall draft picks, Simeon Rice and Kevin Hardy, as well as, Butkus award winner Dana Howard. Illinois led the nation in total defense for most of Holecek's senior season. Illinois participated in college bowl games each of Holecek's seasons.

John Francis Holecek (born May 7, 1972) is a former professional American football player who played linebacker for eight seasons in the NFL for the Buffalo Bills, the San Diego Chargers, and the Atlanta Falcons. He went to college at University of Illinois at Urbana-Champaign. He was drafted by the Buffalo Bills in 1995, went to the San Diego Chargers in 2001, and last played for the Atlanta Falcons in 2002. Holecek played in the NFL for 8 seasons, and then returned to Chicago area. He currently coaches football at Loyola Academy - who won the 2015 and 2018 Class 8A Illinois Football State Championships. Holecek was a finalist for the 2015 National Coach of the Year award.