15. Milwaukee Brewers
When the Brewers re-signed Yelich for $215 million through 2028, the presumption was they were getting a perennial contender for the batting title. The Most Valuable Player for Milwaukee in 2018 and runner-up in 2019, he had won batting titles both seasons, adding the slash line triple crown in 2019.
Both the $215 million raw figure and the resulting $23.9 million AAV are richest in franchise history.
It would take a batting coach, possibly working in tandem with a sport psychologist, to figure out what has gone wrong since. But Yelich’s offense has gone Hindenburg since 2019, plummeting 124 percentage points to .205 in 2025 and recovering since then only to the .250s.
Given the franchise’s small market status, it may not be surprising that Milwaukee’s love affair with Yelich is so much deeper from a dollar standpoint than its commitment, either current or historical, to any other player.
For the moment, second on Milwaukee’s list is recently departed center fielder Lorenzo Cain. Prior to the 2018 season, Cain signed a five-year, $80 million deal that just expired.
That’s $135 million less than the Brewers will have paid Yelich by the end of his contract. Not that the Brewers ever got full value from Cain, a part-time player at best after 2019.
That might change before Brandon Woodruff becomes free agent eligible in 2025. He has developed into the ace of Milwaukee’s staff. Assuming his health holds, they’ll have to either pay him big or watch somebody else pay him big.