The St. Louis Cardinals have found their shortstop for the future in Masyn Winn, who has impressed during the early stages of his MLB career. With club control extending through the 2029 season, speculation about a potential contract extension is already brewing. ESPN's Jeff Passan highlighted Winn as a strong candidate for a lucrative megadeal, potentially exceeding $100 million, thanks to his defensive prowess and a promising offensive upside.

Winn, a defense-first shortstop, recorded 14 defensive runs saved in 2024, earning him Gold Glove consideration. His batting performance has also shown promise, slashing .267/.314/.416 with 15 home runs during his rookie year. After a slow start to the 2025 season, Winn has rebounded well post-injury, hitting .311/.373/.578 with two home runs since returning. The Cardinals may face tough decisions ahead, especially as other young stars, like Lars Nootbaar and Brendan Donovan, are also approaching free agency, while the organization has been historically cautious with big contracts.