Pittsburgh Pirates swing big but face an icy reception on the MLB market. Can breaking the ice with a bold signing truly change their reputation—or just make them look foolish? Gary Morgan examines the Pirates’ aggressive pursuits of Jorge Polanco, Adolis Garcia, and Kyle Schwarber, spotlighting the team’s willingness to outbid rivals and the risks of overpaying for players who may not move the needle. Key talking points include the difference between smart and desperate spending, the challenge of escaping Pittsburgh’s reputation as MLB’s perennial patsy, and strategy for future roster upgrades. From no-trade clauses to lineup construction, speed concerns, and potential targets like Stephen Kwan and Cody Bellinger, Gary Morgan explores the tough choices facing GM Ben Cherington. Are the Pirates finally ready to be taken seriously—or just setting themselves up for another disappointment?