His offspring include Authentic (2020 American Horse of the Year), Mandaloun (2021 Kentucky Derby), Life Is Good (Breeders' Cup Dirt Mile) and Covfefe (female sprint Champion).

Into Mischief was bred in Kentucky by James T. Hines Jr.[2] He was from the first crop of Harlan's Holiday, a Grade I-winning grandson of Storm Cat.

He got involved in a three-way duel for the lead on the outside of Massive Drama and Sky Cape, who tired after a half mile and finished tenth.

"[6][9] Into Mischief started his three-year-old campaign in the San Vicente Stakes at Santa Anita on February 10, 2008, dropping back in distance to seven furlongs.

His training for the race had been interrupted when Santa Anita was shut down several times because a newly installed synthetic dirt surface failed to drain properly after heavy rains.

Into Mischief started to edge away in the stretch but shied when jockey Victor Espinoza went to the whip, briefly shifting leads.

"[12] However, Into Mischief developed an abscess in his left hind hoof and missed several weeks of training, taking him off the Triple Crown trail.

He was the favorite in a seven-horse field that also included Colonel John (Santa Anita Derby, Travers Stakes), Bob Black Jack (Sunshine Millions Dash), Nownownow (Breeders' Cup Juvenile Turf) and Georgie Boy.

[16] Bob Black Jack, who had set a world record for six furlongs earlier in the year, went to the early lead and was never headed, winning by 2+1⁄4 lengths.

[15] In order to build support, Hughes offered a lifetime breeding right to breeders who completed "stands and nurses" contracts in each of his first two years at stud.

The crop he sired in 2013 reached racing age in 2016 and started to move Into Mischief steadily up the North American stallion ranks.

[27] In 2021, his offspring Mandaloun finished second in the 2021 Kentucky Derby and was later declared the winner after Medina Spirit was disqualified in February 2022 due to a positive drug test.

[28] Into Mischief led the North American sire list for the third straight year, breaking his own progeny earnings record in the process.