Tampa Bay organization In 1997, Montoyo joined the Tampa Bay Devil Rays' organization – the year before the
expansion team played its first Major League game – as manager of the Rookie-level
Princeton Devil Rays. After leading Princeton to a 39–30
win–loss record in 1997, Montoyo managed the 1998 Short Season-A
Hudson Valley Renegades, where he won his first division title. In 1999–2000, he managed the
Charleston RiverDogs, leading them to their first winning season. He then was the pilot of the
Bakersfield Blaze of the High Class A
California League in 2001–2002. For the next four years, he served as the manager of Tampa Bay's
Double-A clubs, the
Orlando Rays (2003) and
Montgomery Biscuits (2004–2006), where he won the
Southern League championship in 2006. In 2007, Montoyo became manager of Tampa Bay's top
farm team, the Durham Bulls. Under his leadership, Durham had only one losing season and exceeded 80 wins five times in his first seven years. In 2010, the Bulls set a franchise Triple-A record for wins with 92. In both 2009 and 2013, they won the
Governors' Cup, emblematic of the championship of the International League. Through 2015, his career minor-league managing record was 1,341–1,211 (.525). Montoyo was a coach for the
Puerto Rican 2009 World Baseball Classic team. Also, he was selected to serve as a coach for World Team in the 2010 and 2011
All-Star Futures Game. He won the 2009
Mike Coolbaugh Award and 2010 and 2013
International League Manager of the Year Award. On July 21, 2014, Montoyo surpassed
Bill Evers as the Bulls' all-time winningest manager with his 614th victory at the helm of the Rays' Triple-A affiliate. At the time of his promotion to the Rays, Montoyo had notched 633 wins in a Bulls' uniform. On October 19, 2015, Montoyo interviewed for the
Seattle Mariners vacant managerial position. On October 24, 2015, the Rays hired
Matt Quatraro as their new third base coach and Montoyo became the bench coach, replacing
Tom Foley.
Toronto Blue Jays On October 25, 2018, Montoyo was hired as the manager of the Toronto Blue Jays for the
2019 season. He signed a three-year contract, with a club option for a fourth year. After guiding the Blue Jays to the playoffs in the
2020 season, Montoyo was nominated for AL Manager of the Year award along with
Kevin Cash of the
Tampa Bay Rays and
Rick Renteria of the
Chicago White Sox. On March 16, 2021, the Blue Jays exercised the fourth-year option on Montoyo's contract, tying him to the team through the 2022 season. On April 1, 2022, Montoyo signed a contract extension through the 2023 season, and included team options for 2024 and 2025. Montoyo was fired on July 13 after a 2–9 stretch, despite the team sitting in the third wild card spot.
Chicago White Sox On November 3, 2022, Montoyo was named the bench coach of the
Chicago White Sox, under new manager
Pedro Grifol. On August 8, 2024, Montoyo was fired by the White Sox.
Managerial record ==Championships==