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On May 7, 2019, Colabello signed with the Sugar Land Skeeters of the Atlantic League of Professional Baseball. On June 17, 2019, he was removed from the active roster and placed on the reserve/retired list.

On June 23, 2019, Colabello signed with the Kansas City T-Bones of the American Association. He was released on February 4, 2020.

He played for Team Italy in the 2019 European Baseball Championship. He is playing for the team at the Africa/Europe 2020 Olympic Qualification tournament, taking place in Italy beginning September 18, 2019.

In 2018, Colabello signed with the T&A San Marino of the Italian Baseball League, appearing in a total of 9 games during the season.

In September 2018, Colabello played for the Italian national baseball team in the 2018 Super 6 Baseball Tournament.

Colabello did not make the Indians major league roster, and was assigned to Triple-A. He was released on July 8, 2017, after hitting .225 in 72 games for the Triple-A Columbus Clippers.

Colabello signed a minor league contract with the Milwaukee Brewers on July 18, 2017. He was assigned to the Triple-A Colorado Springs Sky Sox. He hit .301 in 44 games for the Sky Sox, but was not placed on the big league roster when teams expanded to 40 players in September. He played briefly for Charros de Jalisco in the Mexican Pacific Winter League in October and early November, before electing free agency on November 6, 2017.

During spring training, Colabello played in the 2017 World Baseball Classic, appearing at first base in all 4 games in which Italy participated. He went 2-for-13 (.154), with 1 HR and 2 RBI.

On April 22, 2016, Colabello was suspended 80 games without pay for testing positive on performance-enhancing drugs on March 13. This effectively ended his major league career, as Colabello never played another ML game after the suspension began. At the time of his suspension, he was hitting .069 (2-for-29) in 10 games.

On July 13, Colabello was assigned to the Advanced-A Dunedin Blue Jays for a rehab assignment. After rehab, he was assigned to the Triple-A Buffalo Bisons for the remainder of the 2016 season. In 40 games with the Bisons, Colabello hit .180 with five home runs and 11 RBI. On December 2, 2016, Colabello was outrighted to Triple-A Buffalo after clearing waivers. He elected free agency on December 6.

On December 20, 2016, Colabello signed a minor league contract with the Cleveland Indians that included an invitation to spring training.

On November 22, 2016, it was announced that Colabello would play for Italy at the 2017 World Baseball Classic.

Colabello finished the 2015 regular season with career-highs in nearly every statistical category, including batting average (.321), hits (107), home runs (15), RBI (54), and on-base plus slugging (.886). He hit a solo home run in Game 5 of the 2015 American League Championship Series, which helped the Blue Jays top the Kansas City Royals on October 21 and force a Game 6.

In 2014, Colabello made the Twins starting lineup out of the gate, rotating between outfield, first base, and designated hitter. He had a dazzling start to the season, batting .308 with 3 home runs, and 27 RBIs through his first 23 games.

On December 8, 2014, Colabello was claimed off waivers by the Toronto Blue Jays. They designated him for assignment on February 4, 2015, and he was outrighted to the Triple-A Buffalo Bisons on February 11. Colabello batted .337 with 5 home runs and 18 RBI in April 2015, and was named the International League Player of the Month. On May 5, Colabello's contract was purchased by the Blue Jays. In his second game with the Blue Jays, Colabello recorded his first career four-hit game. On May 29, Colabello played his first game against his former team, the Minnesota Twins. In the ninth inning, he hit a tiebreaking two-run home run off closer Glen Perkins to help the Blue Jays win 6–4. Colabello continued his excellent batting on June 7, when he helped the Blue Jays sweep the Houston Astros by hitting a walk-off two-run single. With the hit, he also extended his career-high hitting streak to 17 games. He hit his first career triple on October 2.

On May 22, 2013, the Twins promoted Colabello to the major leagues and he made his debut that day. He was called up after Trevor Plouffe suffered a concussion and was placed on the 7-day disabled list. Colabello went 1-for-11 and was optioned on May 29. He was called back up on May 30 after a strained left calf forced Plouffe to the 15-day disabled list. However, after having played two additional games, Colabello was sent down again when Plouffe returned.

On September 2, 2013, Colabello hit the first major league grand slam off Houston Astros' reliever Chia Jen Lo, and Twins won 10-6.

After his 2013 season, Colabello garnered significant interest from several teams in the Korea Baseball Organization, including a reported $1 million contract offer from the LG Twins (with a similar $1 million buyout going to the Minnesota Twins). On December 21, Colabello announced that he would not pursue the opportunity to play overseas, saying "Going to Korea would mean giving up the dream of being a big-leaguer".

Colabello played for the Italy National Team in the 2013 World Baseball Classic. He appeared in all 5 games that Italy participated in, going 6-for-18 (.333) with 2 HR and 7 RBI.

Prior to joining the Twins organization in 2012, he played seven seasons in the independent Can-Am League for the Worcester Tornadoes (2005–2011) and Nashua Pride (part of 2007).

In 2012, his first season of affiliated baseball, Colabello batted .284 with 78 runs (4th in the league), 37 doubles (leading the league), 19 home runs (tied for 4th) and 98 runs batted in (RBI) (2nd) for the New Britain Rock Cats of the Double-A Eastern League. He started the 2013 season with the Rochester Red Wings of the Triple-A International League, hitting .358 with 12 home runs in 46 games before being promoted to Minnesota.

Born in Framingham, Massachusetts, Colabello grew up in Rimini, Italy. His mother, Silvanna, was born in Rimini, and his father, Lou, played baseball in Italy for seven years, later pitching in the 1984 Olympics. The family moved back to Massachusetts in 1991. Colabello graduated from Milford High School in Milford, Massachusetts. He then attended NCAA Division II Assumption College, but was not drafted by an MLB team.

Christopher Adrian Colabello (born October 24, 1983) is an American professional baseball first baseman and outfielder who is a free agent. He played parts of four seasons in Major League Baseball (MLB) for the Minnesota Twins and Toronto Blue Jays, after playing seven seasons in independent baseball.

Colabello had a very successful minor league season, hitting .352/.427/.639 with 24 home runs (2nd in the league) and 76 RBIs (tied for 2nd) in 89 games, and was named the International League Most Valuable Player at the end of the year, as well as the Rookie of the Year. Called up to the Twins again towards the end of July, Colabello spent the rest of the year in the big leagues, but his .194 average and 7 home runs in 55 games was far off his minor league pace.