Ryan Dempster

3.1. Draft and minor league career

Dempster began his professional baseball career when he was drafted by the Texas Rangers in the third round, as the 66th overall pick, of the 1995 Major League Baseball draft. Following his selection, he commenced his minor league career with the Gulf Coast Rangers. His development in the minor league system also included stints with several other teams, such as the Hudson Valley Renegades, the Kane County Cougars, and the Charleston RiverDogs, where he honed his skills before making his Major League debut.

3.2. Florida Marlins

Dempster's tenure with the Florida Marlins began on August 8, 1996, when he was traded from the Texas Rangers along with Rick Helling in exchange for John Burkett. He made his Major League Baseball (MLB) debut for the Marlins on May 23, 1998, against the Pittsburgh Pirates, where he pitched two innings in relief, allowing three earned runs on two hits. His first start came on June 1, also against the Chicago Cubs, but it was short-lived as he gave up five runs on four hits (including two home runs) and three walks in only one and one-third innings, recording his first career loss. However, he secured his first Major League win on June 28 against the Boston Red Sox, limiting them to just one run over seven innings. He finished his debut season with a 1-5 record and a 7.08 ERA in 14 appearances, 11 of which were starts.

In 1999, Dempster made 25 starts, concluding the season with a 7-8 record and a 4.71 ERA. The year 2000 marked a breakout season for him; he achieved a 14-10 record with a 3.66 ERA in 33 starts. This season included two complete games and one shutout. A notable performance occurred on May 7, 2000, when he pitched a one-hitter against the New York Mets, allowing only a double to Mike Piazza in the sixth inning to secure a complete game shutout. For his stellar performance, he was selected to his first MLB All-Star Game. He also accomplished a rare team pitching triple crown for the Marlins that year, leading the team in wins, ERA, and strikeouts, setting a new club record of 209 strikeouts, surpassing Kevin Brown's previous record of 205 set in 1997. Over the next two seasons with the Marlins (2001-2002), Dempster compiled a combined record of 20-20 with a 4.88 ERA.

3.3. Cincinnati Reds

On July 11, 2002, the Marlins traded Dempster to the Cincinnati Reds in a three-for-one deal for Juan Encarnación, Wilton Guerrero, and Ryan Snare. In the latter half of the 2002 season, he made 15 starts for the Reds, achieving a 5-5 record with a 6.19 ERA.

The 2003 season saw Dempster make 20 starts and two relief appearances, finishing with a 3-7 record and a 6.54 ERA. His season was cut short in August 2003 when he underwent Tommy John surgery on his right elbow, an injury that forced him to miss the remainder of the season. Following the surgery, he was released by the Reds in November 2003.

3.4. Chicago Cubs

After his release from the Reds, Dempster signed with the Chicago Cubs as a free agent on January 21, 2004. He spent time rehabilitating from his Tommy John surgery before joining the Cubs on August 1, where he appeared in 23 games, all out of the bullpen. He recorded his first MLB career save on September 15, 2004, against the Pittsburgh Pirates.

In 2005, after initially starting six games, Dempster was designated as the Cubs' closer, taking over from LaTroy Hawkins. He excelled in this new role, converting 33 saves in 35 opportunities, which was the best save percentage in the league. Notably, in both instances where he blew a save, he still earned the win. He became the only Cubs pitcher, and one of only three players ever, to both start a game and collect 30 saves in the same season. On October 1, 2005, the Cubs extended his contract through 2008 in a deal worth 15.50 M USD. He also shares a club record with Wade Davis for 26 consecutive successful saves.

Dempster emerged as one of the Cubs' most consistent relievers in 2007, recording 16 saves in 18 opportunities before a two-week absence due to an injured oblique muscle. While manager Lou Piniella briefly considered promoting Dempster to a starting role, the struggles of the Cubs' bullpen necessitated his retention as closer.

For the 2008 season, Dempster transitioned back to a starting pitcher role, being assigned the third spot in the starting rotation, with the closer job going to Kerry Wood. On April 3, 2008, he earned his first win as a home starter since 2002. On May 15, 2008, he recorded a career-high 12 strikeouts in a game, pitching eight and one-third innings and allowing only 6 hits. By July 8, 2008, he became the first Cubs pitcher in 31 seasons, since Rick Reuschel in 1977, to achieve a 10-0 record at home. Dempster concluded the 2008 season with an impressive 17-6 record, a 2.96 ERA, and 183 strikeouts in 201 and two-thirds innings. He was selected to the 2008 Major League Baseball All-Star Game, his second career All-Star nod. In 2008, he notably threw sliders 32.9% of the time, more than any other National League starting pitcher, and led the majors in sacrifice hits with 19. Dempster opened the Cubs' 2008 postseason campaign against the Los Angeles Dodgers on September 26, 2008, but after accumulating a high pitch count and failing to get outs with two-strike counts, he surrendered a grand slam to James Loney and was removed from the game.

Following the 2008 season, Dempster re-signed with the Cubs for a four-year contract worth 52.00 M USD. In May 2009, MLB reviewed Dempster's up-and-in pitch to Milwaukee Brewers slugger Ryan Braun. Despite Cubs manager Lou Piniella's comment that "You've got to tie Braun up from time to time," MLB found no wrongdoing and took no action against Dempster. He finished the 2009 season with an 11-9 record and a 3.65 ERA in 31 starts. In 2010, he went 15-12 with a 3.85 ERA in 34 starts, and in 2011, he recorded a 10-14 record with a 4.80 ERA in 34 starts.

3.5. Texas Rangers

On July 31, 2012, at the trade deadline, Dempster was traded back to his original drafting team, the Texas Rangers, in exchange for minor leaguers Christian Villanueva and Kyle Hendricks. He made his Rangers debut on August 2, 2012. During his brief stint with the Rangers, Dempster posted a 7-3 record with a 5.09 ERA in 12 games, pitching 69 innings and recording 70 strikeouts. He became a free agent after the 2012 season.

3.6. Boston Red Sox

Following the 2012 season, Dempster signed a two-year contract with the Boston Red Sox valued at 26.50 M USD on December 19, 2012. This move marked his first experience with a team that would eventually win a World Series.

A significant incident during his tenure with the Red Sox occurred on August 18, 2013, in a game against the rival New York Yankees. When facing Alex Rodriguez, who was embroiled in the MLB doping scandal at the time, Dempster threw one pitch behind him, and then his 3-0 pitch struck Rodriguez on the left elbow pad, ricocheting off his back. This action, which was met with loud cheers from the Fenway Park crowd, was later revealed by Dempster in August 2016 to have been intentional, driven by his personal sense of justice regarding Rodriguez's alleged drug use stemming from Biogenesis of America. Home plate umpire Brian O'Nora warned Dempster and both dugouts, but Dempster was permitted to remain in the game. Later, in the sixth inning, Rodriguez hit a home run off Dempster, and the Red Sox ultimately lost the game 9-6. On August 20, MLB imposed a five-game suspension on Dempster and an undisclosed fine for hitting Rodriguez; although he did not miss a start due to the suspension.

Dempster concluded the 2013 regular season with an 8-9 record and a 4.57 ERA in 32 games (29 starts). He was included on the 25-man active roster for the postseason, making three relief appearances. He achieved his first career championship title when the Red Sox defeated the St. Louis Cardinals in the 2013 World Series.

3.7. Retirement and post-playing career

On February 16, 2014, Ryan Dempster announced his decision to sit out the entire 2014 MLB season, citing a desire to spend more time with his family, as well as a neck injury. Consequently, the Red Sox placed him on the reserve/retired list for the season, which meant he did not receive his full season salary of 13.25 M USD.

Dempster officially announced his retirement from professional baseball on October 8, 2014. Shortly after, on December 5, 2014, he returned to the Chicago Cubs organization, accepting a position in the front office as an assistant to Jed Hoyer, the general manager, and Theo Epstein, the president of baseball operations.

In January 2017, Dempster confirmed his intention to pitch for Team Canada in the 2017 World Baseball Classic. He made two starts for Canada in the tournament, though his performance was limited, as he pitched only two and one-third innings in total while giving up seven earned runs.

5.1. Personality and philanthropic activities

Dempster's personality was further exemplified in March 2007 when he humorously remarked to an Arizona newspaper that if his career as a closer faltered, he would pursue ninja training. Beyond his playful demeanor, Dempster is known for his sincere commitment to philanthropic activities. His dedication to charitable causes earned him nominations for the prestigious Roberto Clemente Award in both 2006 and 2008, an honor recognizing players who best exemplify the game of baseball through their positive contributions on and off the field, including sportsmanship and community involvement.

5.2. Family and health awareness

In early June 2009, Ryan Dempster publicly shared a deeply personal aspect of his family life, revealing that his daughter, Riley Dempster, had been diagnosed with DiGeorge Syndrome. This genetic condition is also known by several other names, including Velo-cardio-facial syndrome (VCFS), 22q11.2 deletion syndrome, and Shprintzen syndrome (named after Dr. Robert Shprintzen, who identified it in 1978). Approximately one in 1,800 babies are born with this genetic deletion, which can ubiquitously affect critical functions such as swallowing, breathing, and speech.

Dempster's decision to disclose his daughter's condition was driven by a desire to raise public awareness for this genetic disease. When questioned about whether Riley would lead a normal life, he expressed cautious optimism, stating, "Yeah, she will. There can be (problems), but so far all the signs are good. There's a lot of work to do. They say there are 186 symptoms you can have. You just check off ones as you go along." After approximately two months in the hospital, Riley was able to return home in early June, bringing a degree of relief to the family. His public advocacy underscored his commitment to using his platform for social good and supporting those affected by genetic conditions.

5.3. Major controversies

While generally known for his positive and easy-going personality, Ryan Dempster was involved in a notable on-field controversy that highlighted his strong sense of justice. This incident occurred on August 18, 2013, during a game between his team, the Boston Red Sox, and the rival New York Yankees. The focal point of the controversy was Yankees third baseman Alex Rodriguez, who was then embroiled in a highly publicized doping scandal related to Biogenesis of America.

In his first at-bat against Rodriguez during that game, Dempster threw a pitch behind him as a perceived warning. Later in the same at-bat, on a 3-0 count, Dempster intentionally threw a fastball, measured at approximately 93 mph ^{(150 km/h)}, that struck Rodriguez on his left elbow pad and ricocheted off his back. This action, believed to be a deliberate expression of Dempster's personal indignation over Rodriguez's alleged use of performance-enhancing drugs, immediately escalated tensions on the field, leading to both benches clearing and a brief altercation. The Yankees' manager, Joe Girardi, was ejected from the game due to his heated protest of the incident.

Although home plate umpire Brian O'Nora issued a warning to both dugouts, Dempster was allowed to remain in the game. However, the incident was far from over; in the top of the sixth inning, Rodriguez hit a home run off Dempster, and the Red Sox ultimately lost the game 9-6. The controversy led to disciplinary action from Major League Baseball, which, on August 20, imposed a five-game suspension and an undisclosed fine on Dempster for intentionally hitting Rodriguez. For several years following the event, Dempster publicly denied that the act was intentional, but he eventually admitted in August 2016 that he had indeed meant to hit Rodriguez. This incident became a lasting example of a player taking a personal stance against perceived ethical breaches within the sport, reflecting Dempster's principled character.