In 2017, Bakero won the MAC Hermann Trophy, an annual award given to the top college soccer player in the United States.

Bakero played college soccer for Wake Forest in the Atlantic Coast Conference, where he was a regular starter all four years.

During his sophomore year, Bakero improved on his freshman campaign and scored eight season goals, and would go on to earn Third Team All-ACC recognition.

In his junior year, Bakero played an integral part of the 2016 Wake Forest team that earned their first ACC Men's Soccer Championship since 1989, and their first berth in the NCAA College Cup Final since 2007.

In between his junior and senior years, Bakero returned to the PDL where he scored five times in seven appearances for the Carolina Dynamo.

On 20 July 2018, Bakero was traded by Chicago Fire to Toronto FC along with $50,000 in General Allocation Money in exchange for Nicolas Hasler.