After retiring from the
NFL, Holecek returned to
Illinois to work in finance and assist coaching high school football at
St. Ignatius College Prep in Chicago. He joined
Loyola Academy in 2006 as the head coach of the Ramblers football program. 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 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. Loyola was the 8A state championship runner-up in 2013, after losing to Naperville Central 13–10 in the title game. Loyola won the Chicago Prep Bowl 14–7 over Chicago Curie at Soldier Field on November 28, 2014. In 2015, Holecek became the fastest head coach in Illinois high school football history to win 100 games. At the close of the regular season in October, Loyola ranked No. 1 in the Illinois in all major football polls after completing a 9–0 undefeated regular season. In November, Loyola defeated the defending 8A champion Stevenson, Homewood Flossmor, and then Palatine in the Semi-Finals. Loyola defeated Marist 41–0 to win the IHSA class 8A State Championship, extending its season record to 14–0. Loyola finished the regular 2016 season 9-0 and ranked #1 in the state as the Ramblers. 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. Loyola finished as runner-up in 2016 in class 8A. 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. 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. Loyola won the 8A championship 13-3 over unbeaten Lincoln Way East at Illinois' Memorial Stadium in November 2022. In early December 2022, Holecek announced that he would be leaving Loyola at the end of the school year when the last of his three sons would graduate. He was succeeded by former assistant Beau Desherow. Holecek's coaching career concluded with him having Loyola's all-time win record and the highest winning percentage (84%) amongst active Illinois high school coaches. His other accomplishments include: 185 wins, 9 Chicago Catholic Championships, 17 consecutive playoff appearances, 7 state finals appearances , and 3 championships. Holecek's teams qualified for the playoffs every year since 2006, including 16 IHSA State Playoff appearances. He led Loyola to four consecutive State Final games from 2015–2018. The NFL's PlayFootball regarded Holecek as one of the top high school football coaches in the country in 2021. In 2024, Loyola defeated
York Community High School to win a third-consecutive state championship. In Spring 2025, Holecek traveled to Italy to temporarily become the defensive coordinator for the
Italian Football League's
Milano Seamen. ==References==