On February 16, 2014, Dempster announced he would not pitch or engage in any baseball activities for the entire 2014 year, stating that he wanted to spend some time with his family. The Red Sox placed Dempster on the reserve/retired list for the 2014 season and elected not to grant him a full season salary worth $13.25 million. On October 8, 2014, Dempster officially announced his retirement. On December 5, it was announced that Dempster would be taking a job in the Cubs' front office as an assistant to general manager Jed Hoyer and president of baseball operations Theo Epstein. In January 2017, Dempster indicated he would pitch for Team Canada in the 2017 World Baseball Classic. He started two games for Canada in the Classic, pitching a total of only innings while giving up 7 earned runs. Broadcasting career On April 22, 2014, Dempster was hired by MLB Network as a studio color analyst. In 2020, Dempster joined the newly-launched Marquee Sports Network as a studio and game analyst for Cubs telecasts. Pitching style Dempster threw five pitches with some regularity: a four-seam fastball and two-seam fastball averaging about 90 mph, a cut fastball in the high 80s, a slider in the mid 80s, and a splitter in the low 80s. Dempster favored his slider over his splitter when throwing to right-handed hitters and often imparted an obvious, prolonged wiggle to his glove as part of his windup, a move he claims is done in order to prevent tipping opposing batters to his pitches. Personal life Dempster is widely known for his laid-back attitude, constantly joking with fans and teammates, and is said to be a positive contribution to a team's clubhouse. Dempster's fun and easy-going personality was especially evident when, in comments to an Arizona newspaper in March 2007, Dempster stated that if his career as a closer began to tumble, he would pursue ninja training. In early June 2009, Dempster released a statement explaining that his daughter, Riley Dempster, had DiGeorge Syndrome, also known as Velo-cardio-facial syndrome (VCFS), 22q11.2 deletion syndrome, and Shprintzen syndrome (after Dr. Robert Shprintzen who identified it in 1978). About 1 baby in 1800 is born with this genetic deletion which ubiquitously affects swallowing, breathing, and speech. Dempster did this because he wanted to help raise awareness of this genetic disease. When asked if she would lead a normal life, he replied, "Yeah,