Riding a pair of full siblings for the 2026 futurity season, Heavens Gone Wild and Heavens Wild Side, Montgomery earned over $90,000 over the recent weekend in Unadilla. Heavens Gone Wild and Heavens Wild Side are both sired by JL Dash Ta Heaven and out of LegsGoneWild. The duo of Heavens Gone Wild and Heavens Wild Side finished second and third in the Open 1D and High Stakes 1D on Friday. The run earned the 1D Derby win, as well as the Saturday Open 1D, and Saturday High Stakes 1D. Chasin A Win finished third in the Derby 1D, and fourth in both the Open 1D and High Stakes 1D.