Bakero played college soccer for Wake Forest in the Atlantic Coast Conference, where he was a regular starter all four years. In total, Bakero made 88 appearances for the Demon Deacons, scoring 37 goals across all competitive matches. Bakero made his debut for Wake Forest on 29 August 2014 in a 3–1 loss against UCLA. A month later, he would earn his first points with Wake Forest, notching an assist against Akron on 30 September 2014, in a 2–1 victory. In the following match, on 3 October 2014, Bakero scored his first collegiate goal against Duke in a 4–1 victory. Bakero would score multiple times two weeks later. 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. Between his sophomore and junior years, Bakero played for FC Tucson in the Premier Development League, a off-season amateur league that allows college soccer players to retain their NCAA eligibility while still playing competitively during the offseason. Bakero finished the 2016 PDL season with one goal in eight appearances for Tucson. 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 Finalsince 2007. Bakero earned All-ACC Tournament XI honors and College Cup Best XI honors. In between his junior and senior years, Bakero returned to the PDL where he scored five times in seven appearances for the Carolina Dynamo. Bakero lead the Deacs in scoring for his senior year, where he notched 16 goals in 23 appearances. He helped Wake Forest successfully defend their ACC Tournament title, and reach the quarterfinals of the NCAA Tournament. He was awarded with First-Team All ACC honors, the ACC Men's Soccer Offensive Player of the Year and the Hermann Trophy, which is given annually by the Missouri Athletic Club to the best college soccer player in the United States.
Professional
Ahead of the 2018 Major League Soccer season, it was announced that Bakero had signed a contract with Major League Soccer, making him eligible for the 2018 MLS SuperDraft. He was an expected first round draft pick. Bakero was selected by Chicago Fire SC with the fifth overall pick in the SuperDraft. Bakero made his professional debut on April 14, 2018 as an 85th minute substitution in a 0–1 loss to the LA Galaxy. 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. Jon made his TFC debut in their 3-2 loss to NYCFC on August 11. In 2019, he was loaned to Phoenix Rising FC After the season, he signed a permanent contract with Phoenix Rising.
Honors
Individual
Hermann Trophy: 2017
ACC Men's Soccer Offensive Player of the Year: 2017
