Jack Flaherty, the Detroit Tigers’ star pitcher, has never shied away from big moments. But in early 2025, he made a decision that raised eyebrows across the MLB, defying the concerns of manager AJ Hinch and teammates: he chose to sign a two-year, $35 million contract with the Tigers, including an opt-out after one season, despite lucrative offers from bigger-market teams like the Los Angeles Dodgers, where he won a World Series in 2024. Was this a gamble on himself, or a choice he’ll live to regret?

Flaherty’s journey has been one of resilience. After a standout 2024 with the Dodgers, where he posted a 3.58 ERA over 10 starts, he became a free-agent prize. The Dodgers, flush with stars like Blake Snell, didn’t re-sign him, leaving Flaherty to weigh his options. Reports suggest Hinch and teammates, including Cy Young winner Tarik Skubal, urged caution about returning to Detroit, citing the team’s inconsistent offense and bullpen struggles. They feared the pressure of a smaller market could expose Flaherty’s recent inconsistencies, like his 4.61 ERA in 2025 and league-high nine home runs allowed by May.

Yet Flaherty, a Burbank native who cherished his Dodgers stint, saw Detroit as home. He valued the camaraderie with Skubal and the chance to anchor a rotation with young talents like Jackson Jobe. “I’m happy here,” he said at spring training, brushing off doubts. His March 29 start against the Dodgers, where he threw nearly six quality innings, earned praise from Hinch: “I love how Jack came out today.” But skeptics point to his sixth-inning woes—opponents are 11-for-21 against him this season—and wonder if Detroit’s defense can support him.

The decision carries risks. Flaherty’s opt-out clause bets on a stellar 2025 to secure a bigger deal, but his recent struggles, like a May 10 outing where he allowed five earned runs in three innings, raise red flags. If injuries or inconsistency persist, he could miss the financial security a longer contract elsewhere offered. Hinch, known for forward-thinking management, reportedly worried about Flaherty’s workload after a grueling 2024 postseason.

Will he regret it? Flaherty’s grit suggests no. His spring training performance—four scoreless innings against the Braves—showed flashes of dominance, despite command issues. With Detroit’s rotation poised to be among the league’s best, Flaherty could silence doubters. For now, he’s betting on himself, and Tigers fans are along for the ride. Only time will tell if this bold move cements his legacy or becomes a cautionary tale.