Cheever was born in Rome and grew up in Europe. He began karting in 2006, working his way through the junior ranks on the European circuit and progressing to the KF2 category by 2009, when he finished 15th in the CIK-FIA European Championship.
Cheever graduated to single-seaters in 2009 with Jenzer Motorsport, competing in both the Swiss and Italian Formula Renault championships and finishing eleventh and fourteenth in their respective final standings. In 2010 he moved to the newly launched Formula Abarth series in Italy, remaining with Jenzer Motorsport. He achieved a podium in the sprint race at Varano and ended the season eleventh overall.
The 2011 season brought him into the Italian Formula Three Championship with Lucidi Motors, where he secured podiums at Misano, Adria and Mugello on the way to ninth in the standings. For 2012 he joined Prema Powerteam and produced his best single-seater results, finishing runner-up to Riccardo Agostini in both the European and Italian championship formats of the series. That performance earned him a test in a Scuderia Ferrari Formula One car at Vallelunga on 9 November 2012. He continued with Prema into the FIA Formula 3 European Championship in 2013.
In 2014 Cheever switched from open-wheel to stock cars, racing in the NASCAR Whelen Euro Series for Italian-based CAAL Racing. He scored his first win and first pole position at Brands Hatch, then added victories at Magione and Le Mans, finishing third in the final points standings. He also claimed the Jerome Sarran Trophy, awarded to the highest-placed driver aged 25 or under, and the Race And Win Pole Award for the season's most pole positions.
In August 2015 Cheever made his K&N Pro Series East debut at Watkins Glen International for Bill McAnally Racing, and also ran one race in the K&N Pro Series West at All American Speedway, again for Bill McAnally Racing.
Cheever became a long-standing member of the Sky Tempesta Racing team alongside Chris Froggatt and Jonathan Hui, contesting GT endurance events across Europe. In 2023 the team began a partnership with Garage 59 and switched to the McLaren 720S GT3 for competition in the GT World Challenge Europe. He has also competed in the FIA World Endurance Championship and at the 24 Hours of Le Mans, and races in the IMSA SportsCar Championship in the GTD class with Triarsi Competizione.
Cheever embodies a second generation of international motorsport within his family, following his father's Formula One and IndyCar career. His results across NATO Euro Series competition, Italian Formula Three, and GT endurance racing established him as a versatile professional driver capable of competing across both open-wheel and GT disciplines on multiple continents.
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