Drake Caggiula

Growing up in Pickering, Drake Caggiula was coached and mentored by his father between the ages of eight and fifteen, an early period that shaped his approach to the game. He played minor midget with the Ajax/Pickering Raiders before moving on to junior options that preserved his NCAA path.

Instead of joining the OHL after being selected in the third round by the Erie Otters, Caggiula chose the Stouffville Spirit of the OJHL to keep college eligibility. He earned first-team all-prospect honours in the OJHL as a rookie, helped Stouffville capture its first OJHL title while being named playoff MVP, and participated in events such as the Central Canada Cup Challenge. He was also drafted by the Des Moines Buccaneers of the USHL and attended their Fall Classic before committing verbally to the University of North Dakota.

At North Dakota (2012–2016), where he majored in kinesiology, Caggiula played left wing and established himself quickly: 39 games as a freshman with strong production among rookies, participation in the 2014 Frozen Four, and later conference and national recognition. His senior year culminated in the 2016 NCAA championship; he earned Most Outstanding Player of the tournament and spots on NCHC and All‑American teams, which made him one of the top collegiate free-agent prospects that spring.

He signed a two-year entry-level contract with the Edmonton Oilers on May 7, 2016. After an injury delayed his start, he debuted in the NHL on November 19, 2016 and scored his first NHL goal on December 3, 2016 in an overtime win. Caggiula re-signed with the Oilers in June 2018, was traded to Chicago on December 30, 2018, scored his first Blackhawks goal on February 1, 2019, and went on to post 9 goals and 15 points in 40 games during 2019–20. He became a free agent in October 2020, signed with the Arizona Coyotes in December 2020, was placed on waivers and claimed by the Buffalo Sabres in April 2021, re-signed with Buffalo in July 2021, joined the Pittsburgh organization on a one-year two-way deal in July 2022, returned to Edmonton on a two-year two-way contract in July 2023, and signed with Lausanne HC of Switzerland's National League on June 2, 2025.

A left winger by trade, Caggiula has filled depth and support roles at the NHL level, offering occasional scoring and a dependable presence in lower-line assignments according to the progression of his career.