Milwaukee Brewers president of baseball operations Matt Arnold has been recognized as the best in the business after becoming the first two-time Executive of the Year winner, but it has not entirely shielded him, and the Brewers front office, from criticism.

Recently, Bleacher Report took exception to Milwaukee’s offseason thus far, putting the Brewers on its list of “MLB’s Biggest Winners and Losers of Free-Agent and Trade Seasons So Far.”

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“It has become an annual rite of passage at this point: We bemoan the Brewers’ uninspiring winter, but then they enter October as one of the viable candidates to win it all anyway,” it wrote. “This time around, though, the bummer isn’t that they lost a key player like Corbin Burnes or Willy Adames, but rather that their qualifying-offer gambit on Brandon Woodruff turned into an expensive one.”

“Had Woodruff declined the offer, Milwaukee would’ve gotten a solid compensatory draft pick once he signed elsewhere. Instead, he’s back for one more year at $22.025M, becoming the highest-salaried pitcher in franchise history.”

When healthy, Woodruff is an undeniable ace. He has been a two-time All-Star and has compiled a 25-7 record over the last three seasons he has been able to play, but injuries have severely hampered him.

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“Sure, they’ll be happy to have him back on the mound for however many innings he’s healthy enough to pitch in 2026. But after having to pay him $10M when he declined his $20M mutual option, that additional $22.025M is tough to swallow/budget.”

“Though the buyout doesn’t count against their payroll for luxury-tax purposes, it’s not like the Brewers are ever worried about paying a tax. Altogether, that is $32.025M in one year for a team that has opened each of the past two seasons with a payroll of around $105M, devoted to a pitcher who has made a combined 23 starts over the past three years.”

Woodruff underwent a major right shoulder surgery in 2023 that forced him to miss the 2024 season and a good chunk of last season. However, he went 7-2 with a 3.20 ERA and a 0.91 WHIP. Nevertheless, the Brewers are up for an expensive gamble.

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“At least they’ve got Freddy Peralta for $8M, provided they don’t trade him away?”

“The Brew Crew subsequently traded breakout outfielder Isaac Collins and right-handed reliever Nick Mears to Kansas City for left-handed reliever Ángel Zerpa, which was a bit of a head-scratcher. We’ll see if they can afford to do any more spending.”