Heslip attended Nelson High School in Burlington, Ontario where he was a three-time Halton all-star honoree and team captain in 2008–09. As a senior, he averaged 28 points, four rebounds and four assists per game. In February 2009, he scored a school-record 54 points in Nelson's game against Notre Dame. He also earned MVP honors at the 2009 All-Canada Classic. During the 2009 Fall semester, Heslip attended New Hampton School in New Hampton, New Hampshire where he averaged 15 points and seven rebounds before enrolling at Boston College.
College career
Heslip went mostly unrecruited, receiving an offer to play from only the University of Guelph in Ontario. However, he raised his stock after a solid summer playing in the Amateur Athletic Union. In December 2009, he joined the Boston College Eagles men's basketball team where he participated in practice but did not play for them in 2009–10. In April 2010, Heslip announced his decision to transfer from Boston College. On June 9, 2010, Heslip signed a National Letter of Intent to play for Baylor University, and subsequently sat out the 2010–11 season due to NCAA transfer regulations. During 2010–11, he was named to the Big 12 Commissioner's Honor Roll for both the fall 2010 and spring 2011 semesters. As a redshirted sophomore in 2011–12, Heslip was named to the Big 12 All-Tournament team, Academic All-Big 12 second team, Las Vegas Classic All-Tournament team and Big 12 Commissioner's Honor Roll for both the fall 2011 and spring 2012 semesters. In 38 games, he averaged 10.2 points, 1.3 rebounds and 1.0 assists in 27.1 minutes per game. As a junior in 2012–13, Heslip was named to the Academic All-Big 12 first team and Big 12 Commissioner's Honor Roll for both the fall 2012 and spring 2013 semesters. On April 4, 2013, he helped Baylor win the 2013 National Invitation Tournament championship with a 74–54 win over Iowa in the final. In 36 games, he averaged 8.6 points and 1.4 rebounds in 26.3 minutes per game. As a senior in 2013–14, Heslip played 38 games and averaged 11.7 points and 1.3 rebounds in 27.4 minutes per game.
Professional career
2014–15 season
After going undrafted in the 2014 NBA draft, Heslip joined the Minnesota Timberwolves for the 2014 NBA Summer League where he shot 7-for-10 on three-point field goals in five games. On September 18, 2014, he signed with the Timberwolves, but was later waived on October 25 as one of their final cuts from training camp. On November 1, 2014, he was selected by the Reno Bighorns with the 11th overall pick in the 2014 NBA Development League Draft. Playing under new Reno coach David Arseneault Jr., who was installing a fast-paced system based on his father'sGrinnell System, Heslip scored 78 points and made 20 three-pointers in his first two D-League games. In his professional debut on November 14, he shot 11-of-18 to set a D-League single-game three-point shots made record against the Iowa Energy, and 15 days later he shot 13-of-20 to break his own record against the Idaho Stampede. His final game with the Bighorns came on January 18, 2015, after which he left the team in order to sign in Europe. On January 23, 2015, Heslip signed with Bosnian club Igokea for the remainder of the season. With Igokea, he was named the 2015 Bosnian Cup Grand Final MVP after helping his team win. In 15 Bosnian national league games for Igokea, he averaged 18.3 points, 2.6 rebounds and 1.3 assists per game. He also averaged 23.7 points in seven Adriatic League games.
On September 20, 2016, Heslip signed with the Toronto Raptors. However, he was later waived on October 22 after appearing in four preseason games. On October 30, he was acquired by Raptors 905, Toronto's D-League affiliate team.
Heslip is the son of Jody Triano and Tom Heslip. His father was an All-Canadian player at the University of Guelph in 1980. His uncle, Jay Triano, played for the Canadian national team for 11 years and later became the national team head coach. Jay is also the former head coach of the Toronto Raptors and is currently an assistant coach for the Charlotte Hornets.
