Yankees have four of top-20 best free agent signings in MLB history

ASFN Admin · Apr 10, 2026

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Yankees have four of top-20 best free agent signings in MLB history originally appeared on The Sporting News. Add The Sporting News as a Preferred Source by clicking here.

The New York Yankees have the most success of any team in not just Major League Baseball history, but arguably all of professional sports history as well.

But that's regarding their on-field performance. What about the front office and the moves they make?

Across the last 50 years of free agency, the Yankees have made a ton of great moves, and are featured four times on Bradford Doolittle of ESPN's top-20 best free agent signings in MLB history.

Yankees have four of top-20 best free agent signings in MLB history

The Yankees' best free agent signing, according to Doolittle, was the 1978 signing of Rich Gossage, who agreed to a $3.6 million deal over six seasons, placing 11th all-time.

He put up 18.6 bWAR and was an overall high-quality reliever signing who received a score of 520.7 points according to Doolittle's scoring system.

Aaron Judge and his $400 million nine-year deal place 14th all-time with a 479.1 score, despite being just three seasons into this massive deal.

But his production has been more than good enough to justify this ranking, and he could easily climb this leaderboard as well.

More: Shohei Ohtani deemed more valuable than Aaron Judge in recent ESPN discussion piece

Next for the Yankees, coming in at 17th overall, was the five-year, $3.5 million signing of Reggie Jackson back in 1977, with a score of 441.5. He put up 17.2 bWAR with the Yankees, was one of the best hitters in MLB history, and is a Hall of Famer.

Rounding out the Yankees' presence inside the top 20 is Dave Winfield, who places 20th overall with a 433.3 score for his 10-year, $23 million deal back in 1981.

He put up 27.1 bWAR while making multiple All-Star teams, winning multiple Gold Glove Awards, and averaging 25 homers in the first eight seasons of this deal.

All-in-all, the Yankees' presence inside the top-20 best free agent signings of all time is strong, but they lack the top-10 presence. But Judge could join such a group, as he's carving out what might be an all-time great career.

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Yankees have four of top-20 best free agent signings in MLB history

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