Windom was born on December 24, 1990, and developed his racing career through the traditional American open-wheel grassroots pathway. His success in USAC competition across multiple disciplines established him as one of the more versatile American open-wheel drivers of his generation.
Windom's USAC career is the centerpiece of his racing identity. He won the 2016 USAC Silver Crown Championship and followed that with the 2017 USAC National Sprint Car Championship, then added the 2020 USAC National Midget Car Championship to complete the Triple Crown — only the seventh driver ever to achieve the feat.
Beyond the championships, Windom accumulated a strong record in marquee USAC events. He is a two-time Indiana Sprint Week champion (2011, 2018) and a two-time Eastern Storm champion (2017, 2018), both prestigious multi-race USAC sprint car series contested on Pennsylvania and Indiana tracks respectively. He also claimed two victories in the Little 500 sprint car race at Anderson Speedway (2011, 2015), one of USAC's most celebrated events.
Windom made several starts in stock car competition alongside his open-wheel commitments. Between 2011 and 2015 he made seven starts in the ARCA Menards Series. In 2017 he made three starts in the NASCAR Camping World Truck Series with MB Motorsports, adding one more in 2018 with DGR-Crosley; his best finish in that series was fourteenth at Eldora Speedway, the series' annual dirt race.
His highest-profile NASCAR appearance came in 2021, when he joined Rick Ware Racing for the NASCAR Cup Series dirt race at Bristol Motor Speedway. Windom finished 33rd after suffering an engine failure. He also substituted for Michael Annett in the No. 02 Young's Motorsports entry in the Corn Belt 150 at Knoxville Raceway.
Windom twice attempted to break into the Indy Lights series via the Freedom 100 at Indianapolis Motor Speedway, a prestigious open-wheel race on the oval. His first attempt in 2018 was arranged through Belardi Auto Racing with backing from Jonathan Byrd's Racing — the same support group that had backed fellow sprint car driver Bryan Clauson's open-wheel crossover. A crash during morning testing on May 21, 2018, caused sufficient damage to the car that Windom withdrew before the race.
A second attempt in 2019, again with Belardi Auto Racing and Jonathan Byrd's Racing, ended more dramatically. The day before the Freedom 100, Windom suffered a heavy crash during the Hoosier Hundred dirt mile at Indiana State Fairgrounds. Despite this, he elected to start the race — only to be collected in a violent first-lap incident when he struck a spinning David Malukas and climbed over the SAFER barrier. Remarkably, neither driver was injured.
Windom's completion of the USAC Triple Crown places him in rare company in American open-wheel history. His dominance across all three USAC national divisions — combined with consistent success in Indiana Sprint Week and Eastern Storm — reflects a broad mastery of both sprint car and midget disciplines that few drivers have matched. While his crossover attempts in NASCAR trucks and Indy Lights produced limited results, they underscored the breadth of ambition that has characterized his career.