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In 2019, Rizzo hit .293/.405/.520 with 27 home runs and 94 RBIs. He led the major leagues in times hit by a pitch with 27. He also received his third career Gold Glove Award.

On April 10, 2018, Rizzo was placed on the disabled list for the first time in his MLB career, due to a back issue. Prior to a May 23 game against the Cleveland Indians, Rizzo ranked fourth in Cubs franchise history with 17 HRs during interleague play. On July 23, Rizzo convinced Cubs manager Joe Maddon to let him make his first career pitching appearance. It took him two pitches to retire A. J. Pollock of the Arizona Diamondbacks on a fly out to center field.

Rizzo finished his 2018 campaign batting .283 with 25 home runs and 101 RBIs in 153 games, and was 3rd in the major leagues in hit by pitch, with 20. Tied for Gold Glove Award votes with Atlanta Braves first baseman Freddie Freeman, Rizzo received the award for the second time in his career.

On February 15, 2018 Rizzo delivered an emotional speech at the vigil for the school shooting victims in Parkland, Florida. Rizzo was a graduate of Marjory Stoneman Douglas High School and a longtime Parkland resident. "I grew up at Stoneman Douglas [High School]," an emotional Rizzo said.

Rizzo had a disappointing postseason. In 37 at bats he had one home run in 5 hits, 6 RBIs and an anemic batting average of .135. On October 27 Rizzo was named as the 2017 recipient of the Roberto Clemente Award for his charity's work to find a cure for childhood cancer. Of winning the award, Rizzo said, "This is amazing. The greatest award you can win. It will go front and center in front of anything I've ever done."

Rizzo chose "Tony" as his nickname for the Players Weekend during the 2017 season.

Rizzo proposed to girlfriend Emily Vakos on June 1, 2017. They met when the Cubs were in Arizona for spring training 2016. The couple was married on December 29, 2018.

Rizzo started as the first baseman at the 2016 All-Star game, receiving the most fan votes in the National League. By the end of the year, Rizzo had become one of three players, and the first left-handed player, in Cubs history to hit over 40 doubles and 30 home runs in the same year. Rizzo played in 155 games with 583 at bats and scored 94 runs. He was hit by a pitch 16 times, had 170 hits with 43 doubles, 4 triples, 32 home runs and 109 RBIs. He finished the year with a batting average of .292 and was fourth in the voting for National League Most Valuable Player. Rizzo's fielding excellence was rewarded with a Gold Glove Award. Rizzo was one of six finalists for the Marvin Miller Man of the Year Award and was the Cubs nominee for the Roberto Clemente Award. After an extremely slow start in the postseason, Rizzo broke out of his slump in the NLCS. He was an integral part of the last three victories over the Los Angeles Dodgers and led the Cubs to their first World Series appearance since 1945. In the 2016 World Series, Rizzo scored 7 runs and had 5 RBIs, and helped the Cubs win their first World Series title since 1908. He also won the Esurance MLB Award for "Best Social Media Personality" and for "Best Play: Defense". Rizzo's defense saved 11 runs for the Cubs which led all MLB first basemen and he was recipient of his first Fielding Bible Award. He also won the fan vote for the Platinum Glove Award.

Rizzo was elected on the player's ballot for the 2015 All-Star Team. 2015 was the second consecutive year that he played in the game. He also competed in the 2015 Major League Baseball Home Run Derby for the first time in his career, but lost in the first round to Josh Donaldson. Rizzo hit his 100th career home run and 300th RBI on September 8, 2015, against Cardinals pitcher Michael Wacha. Rizzo was hit by a pitch 30 times in 2015, leading the major leagues, and joined Don Baylor as the only other member of the 30HR/30HBP club. Rizzo finished the regular season with a .278 batting average, 31 home runs, 38 doubles, and 101 RBI in 701 plate appearances, and led the major leagues in hit by pitch, with 30. He placed 4th in National League MVP voting.

On May 12, 2013, Rizzo agreed to a 7-year, $41 million deal. The deal included two club options that could extend the contract to 9 years and $73 million. He was named as the Cubs finalist for the national Heart and Hustle Award, and he was also named the Cubs finalist for the Roberto Clemente Award. Rizzo placed 2nd for the Gold Glove award for first basemen. Despite having an off year in 2013, Rizzo showed good power, belting 23 homers and 40 doubles in 606 at bats with a .233 batting average.

With the Cubs in a season-long slump and playing .500 baseball, Manager Joe Maddon inserted the power hitting Rizzo into the lead-off spot in an away game against the New York Mets on June 13. In the next seven games the Cubs went 5–2 and Rizzo hit 4 home runs (3 to lead off a game). By June 20, Rizzo had reached base in the first inning in his first seven games as a leadoff hitter and became the first player to reach safely to start the first inning in his first seven career leadoff appearances in over half a century of Major League baseball. He had 12 hits in 28 at bats with 10 RBIs and hit .430 during the streak. Rizzo finished second behind the Nationals Ryan Zimmerman in a tight race for starting NL first baseman in the 2017 All-Star Game. On September 2, Rizzo became the fourth Cubs players to hit at least 30 home runs, 30 doubles, and 100 RBIs in three or more seasons; the others were Hack Wilson, Billy Williams, and Sammy Sosa.

As his family originated in the Sicilian town of Ciminna, Rizzo chose to play for Italy in the 2013 World Baseball Classic before the MLB 2013 season.

On January 6, 2012, the Padres traded Rizzo and right-handed starting pitcher Zach Cates to the Chicago Cubs in exchange for right-handed starting pitcher Andrew Cashner and outfielder Kyung-Min Na. The deal was negotiated by Jed Hoyer, the Cubs' general manager. Hoyer had also drafted Rizzo while working as an assistant general manager for the Red Sox, and later acquired Rizzo while he was the Padres' general manager. He blamed himself for calling up Rizzo to the majors too early in San Diego.

Rizzo started the 2012 season with the Triple-A Iowa Cubs. He again excelled in the minor leagues, batting .342 average with 23 home runs and 62 RBIs before being recalled by the Cubs on June 26. Similar to his call-up in San Diego, he was expected to help a struggling offense.

The Padres invited Rizzo as a non-roster player to their major league camp for 2011 Spring training. He started the 2011 season in Triple-A with the Tucson Padres. In his first 15 games, Rizzo hit .452 with six home runs and 24 RBIs. In May 2011, The San Diego Union-Tribune wrote that Rizzo's debut in the Major Leagues might be delayed by the Padres despite the club's hitting deficiencies due to cost considerations created by the "Super Two" exception for salary arbitration eligibility. The team cited Rizzo's lack of experience above Double-A and his limited exposure to left-handed pitching as benefits of his continuing to play in Tucson.

Rizzo was called up to the majors after hitting .365 with an OPS of 1.159 along with 16 home runs and 63 RBI in 200 at-bats over 52 games in Tucson. The San Diego Union-Tribune called Rizzo "the most celebrated Padres call-up" since Roberto Alomar debuted with the team in 1988. Rizzo's promotion was prompted by the Padres' inadequate offensive production and fielding play of veterans at first base. In his debut on June 9, 2011, against the Washington Nationals, Rizzo struck out in his first at-bat, but then proceeded to hit a triple and score a run, helping the Padres to a 7–3 victory. He hit his first home run on June 11 against John Lannan. After three games he was 3-for-7 with a double, triple and a home run, while he demonstrated patience in drawing four walks for a .667 on-base percentage (OBP). On July 21, 2011 Rizzo was demoted back to Triple-A, and Blanks was promoted. Rizzo had struggled with only a .143 batting average and 1 home run, striking out 36 times in 98 at-bats. Hoyer said Rizzo "worked hard, never made excuses, and endeared himself to his teammates" during his initial stint in the majors. Rizzo was recalled to the majors on September 4 after finishing the season at Tucson batting .331 with 26 homers and 101 RBI in 93 games. He finished his first season in San Diego hitting only .141 with 46 strikeouts in 128 at-bats. Hoyer believed Rizzo would be the starting first baseman for the Padres in 2012 with Jesús Guzmán as the second option. However, Yonder Alonso moved ahead of Rizzo on the team's depth chart after he was acquired by the Padres in December 2011 in a trade for Mat Latos.

On December 6, 2010, Rizzo was traded along with Casey Kelly, Reymond Fuentes, and Eric Patterson to the Padres for three-time All-Star first baseman Adrián González. Rizzo was considered the third best prospect (Kelly was #1) and the best power-hitting prospect in the Red Sox organization. Kevin Boles, Rizzo's manager at Salem, also previously managed González in the minors. Boles said, "Rizzo reminds me a lot of Adrián González ... Rizzo is a bigger kid and has a little more power, Adrian is a little more of a contact hitter, but they had very similar styles of play ... We thought very highly of Anthony Rizzo. He's going to be a heck of a player." Padres General Manager Jed Hoyer expected either Rizzo or Kyle Blanks to eventually be the Padres major league starting first baseman.

Rizzo was diagnosed with limited state classical Hodgkin's lymphoma in April 2008. He went through chemotherapy for six months. His grandmother was battling breast cancer at the same time. On September 2, 2008, Rizzo's doctor told him he was in remission, though he still had six weeks left of treatment and some follow-up testing. On November 18, Rizzo's doctor told him he "could live a normal life." In 2012, the Anthony Rizzo Family Foundation was founded. It is a non-profit 501(c)(3) organization, benefiting cancer research and families fighting the disease. The foundation is run entirely by Rizzo's family, his close friends and his management team. Rizzo provides oversight and leadership. In August 2017 the foundation announced a $3.5 million gift to the Lurie Children's Hospital in Chicago, bringing its total donations to the hospital to more than $4 million.

Rizzo was selected by the Boston Red Sox in the sixth round of the 2007 MLB draft and became a top minor league prospect in the Red Sox organization. He was traded to the San Diego Padres after the 2010 season along with three other prospects in exchange for All-Star first baseman Adrián González. He made his MLB debut in 2011 with San Diego. After being traded to the Cubs in 2012, he developed into an All-Star player, appearing in the All-Star Game three consecutive times, from 2014 through 2016, and winning the Silver Slugger Award, Gold Glove Award and Roberto Clemente Award in 2016, when the Cubs won the World Series.

Rizzo was a sixth-round draft choice out of Marjory Stoneman Douglas High School in Parkland, Florida in the 2007 Major League Baseball draft by the Red Sox. He was heading for Florida Atlantic University before he was drafted and signed, with a $325,000 signing bonus. Rizzo played in the Red Sox organization with the Gulf Coast League Red Sox, Greenville Drive, Salem Red Sox and the Portland Sea Dogs. Rizzo hit 12 home runs in 2009. In 2010, he hit a combined .260 with an on-base percentage (OBP) of .334 and a slugging percentage (SLG) of .480 along with 42 doubles, 25 home runs and 100 RBIs between stops at High-A Salem and Double-A Portland. Rizzo credited the easing of his swing and making better use of his legs for his power surge.

Anthony Vincent Rizzo (born August 8, 1989) is an American professional baseball first baseman for the Chicago Cubs of Major League Baseball (MLB). He has also played in MLB for the San Diego Padres. He is a three-time All-Star. Through his philanthropic ventures, he is a regular finalist for the Heart and Hustle award and is considered by many to be one of the most respected players in Major League Baseball.

He became the first player in Cubs history to have three game-winning RBIs in his first five games with the team. He hit seven homers in July, the most by a Cubs rookie in a calendar month since Mel Hall hit nine in August 1983. He also led National League (NL) rookies that month in homers, hits (32), RBIs (17), and total bases (55). He ranked second among NL rookies in runs scored (14), and he was third with a .330 batting average, .375 on-base percentage and .567 slugging percentage. He was named the league's July Rookie of the Month.

Rizzo had his fifth multi-homer game on May 30, and his second career walk-off home run on June 6. Rizzo was voted into the All-Star game via the final vote by fans along with White Sox pitcher Chris Sale. Rizzo joined teammate Starlin Castro in Minneapolis for the All-Star game. In late July, Rizzo won his first Player of the Week award. In mid-September Rizzo became the youngest player to receive the Branch Rickey Award as "a strong role model for young people". Rizzo finished the season with a combined on-base and slugging percentage of .913 (3rd in the NL), 32 home runs (2nd in the NL) and an at-bats per HR percentage of 16.4 (2nd in the NL), led the majors in hit by pitch (15), and placed 10th in the National League MVP voting.