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Revisiting San Diego's Four Most Successful Free Agent Deals cover image
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Zach Carver
Jan 18, 2026
Updated at Jan 19, 2026, 02:00
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Discover how Hall of Famers and a current superstar shaped San Diego's winning legacy through impactful free agent acquisitions.

The San Diego Padres may not have one of the richest histories in baseball, but they’ve still got an extensive past that included some of the biggest names to ever play the game. In Bleacher Report’s recent article putting together a Mt. Rushmore of each team’s free agent signings, Joel Reuter selected pitchers Goose Gossage, Rollie Fingers, first baseman Steve Garvey, and third baseman Manny Machado.

Gossage had a Hall of Fame 22-year career, four of which were spent with the Padres after signing a $5.5 million deal in 1984. He held opponents to a 2.99 ERA in 197 games in San Diego, recording 83 saves in the process. He was a two-time All-Star with the Padres and finished fifth in Cy Young voting and 13th in MVP voting in 1984. Though he’s most remembered for his time with the New York Yankees, a significant period of Gossage’s Hall of Fame career was played in San Diego.

Fingers played for the Padres for four years after signing a $1.5 million deal in 1976. During his Padres tenure, he led the league twice in saves and was named an All-Star in 1978. Fingers received MVP votes in his first two seasons in San Diego, also being thrown in the Cy Young conversation in 1978. He finished with 108 saves and a 3.12 ERA in 265 games as a Padre.

Another throwback signing, Garvey joined the Padres on a $.6.6 million deal in 1982. San Diego was where Garvey played his final years after 14 years with the Los Angeles Dodgers, but he was still producing at a meaningful level. He was a two-time All-Star for the Padres in 1984 and 1985, recording a .717 OPS and 316 RBIs during his five-year tenure in San Diego.

Machado is the only signing after 1984 to make the Padres’ list, but he’s been the most successful one. Gossage, Fingers, and Garvey were great players, but their best years weren’t in San Diego. Machado has been with the Padres for seven years now after signing a $150 million deal, and he’s still one of the league’s premier third basemen. He’s since extended his deal, keeping him in San Diego until 2034.

Machado has been an All-Star three times for the Padres and has finished in the top three of MVP voting twice. Since joining in 2019, he’s won three Silver Sluggers on his way to a 127 OPS+ in 968 games as a Padre. Recording a 4.1 WAR last season, Machado still shows signs of years of positive baseball despite being 33 years old. Machado’s signing was the first domino to fall for San Diego as they escaped the bottom of the league and turned into a postseason threat year after year. His place on the team’s Mt. Rushmore of free agent signings is well deserved.