Kalish debuted in the major leagues in 2010, and at the end of the season was voted the Red Sox Rookie of the Year.

He started the 2014 season on the Opening Day roster of the Chicago Cubs, and split it between the major league team and Triple-A Iowa.

[1][5][6][7] His brother Jake Kalish is a pitcher in the Kansas City Royals system, and played for Team Israel at the 2017 World Baseball Classic.

Pitching and playing outfield as a four-year starter for Red Bank Catholic High School, he won all-conference and all-division honors.

[9][10][11] As a freshman in April 2003, in his first varsity pitching start, Kalish struck out ten batters in six innings.

[15][16] Baseball America reported that it may be "apocryphal", but that "legend has it that Kalish didn't swing and miss at a single pitch as a high school senior.

"[17] Confirming that, Red Sox scout Ray Fagant, who followed him in high school, said: "He went his entire senior year without a swing and miss once.

[10] As a pitcher, he threw an 88–89 mph fastball, and what his coach called "a good curveball [and] ... a real nice change-up", and had 190 career strikeouts.

"[18] In October 2005, his 42-yard pass under pressure helped seal the school's upset victory over Manasquan in the Shore Conference Liberty Division.

[citation needed] In 2006, he was named the Jersey Shore Sports Hall of Fame High School Male Athlete of the Year.

But he committed to attending the University of Virginia, with whom he signed on scholarship with the understanding that at least for his freshman year he would only play baseball.

[17][24][25] Major League Baseball's Commissioner's Office held up his signing initially, as the amount of money exceeded his draft slot, but approved it by late August.

[17][38] Lowell manager Gary DiSarcina compared him to former major leaguer Darin Erstad, noting their common intensity.

[41][42][43] He struggled in 2008 while coming back from his surgery, as he split the season between the Single-A Greenville Drive and Lancaster JetHawks, despite being awarded the Red Sox organization Player of the Month Award for July and being fifth in the Red Sox system with 19 stolen bases.

[33][45][47] The Red Sox named him their 2009 Minor League Offensive Player of the Year, as for the year he led Red Sox minor leaguers in walks (68), runs (84), and total bases (231), and was second in homers (18), fourth in RBIs (77), and tied for fifth in stolen bases (21).

[48] After the 2009 season, he played in the Arizona Fall League for the Mesa Solar Sox, batting .301 with a .384 on-base percentage.

[57] On December 17, 2014, Kalish agreed to a minor league contract with the Toronto Blue Jays that included an invitation to spring training.

[66] Observing Kalish in spring training in February 2010, Gordon Edes of ESPN wrote: "Remember the name.

[77][79][80][81] Kalish hit his first major league home run into the right-field bullpen at Yankee Stadium off Javier Vázquez, on August 6.

He then hit another grand slam on September 6 at Fenway Park against the Tampa Bay Rays, which tied a Red Sox rookie record, previously accomplished by Bob Zupcic in 1992.

[4][84] Playing center field in late August, sprinting at full speed and then diving sideways he made an eye-opening, somersaulting catch of a ball in mid-air that concluded, as The Providence Journal described it, with him "tucking his elbow for an acrobatic, elegant landing on the Tropicana Field turf, looking like a character from the movie The Matrix" (see video).

After the season, Kalish was voted the 2010 winner of the Harry Agganis Award as Red Sox Rookie of the Year, by the Boston chapter of the BBWAA.

[89]Through March 25, Kalish was leading the team in stolen bases in spring training, with 5, and tied for second in walks, with 6.

[92][93] He would suffer an injury crashing into the wall at McCoy Stadium in late April, causing him to miss the entire 2011 season, except for 8 games in August.

[94] He was optioned to the Pawtucket Red Sox on July 7 to make room for fellow outfielder Ryan Sweeney.

)[98] Kalish underwent cervical fusion surgery in August, which included the removal of a disc in his neck, the use of his own bone to replace it, and the insertion of a metal plate to fuse it together.

[103] On December 13, 2013, Kalish signed a minor league deal with an invitation to spring training with the Chicago Cubs.

[111] On January 9, 2015, it was announced that the deal had fallen through due to unknown reasons, and Kalish returned to free agency.

[120] In July Kalish went on the disabled list with a knee injury and planned to undergo surgery; he anticipated that recovery would take a year, and that he would be unable to play until mid-2017.