Shocking Josh Hader trade evokes painful Boston Red Sox memories

The Red Sox once made a shocking trade with a first-place team akin to the Brewers’ Josh Hader trade

The Milwaukee Brewers shocked the baseball world this week, trading Josh Hader to the San Diego Padres in exchange for left-handed reliever Taylor Rogers, left-handed pitching prospect Robert Gasser, right-hander Dinelson Lamet, and outfielder Esteury Ruiz.

A team that currently leads their division dealing their All-Star closer at the deadline is a stunning move but hardly unprecedented. Boston Red Sox fans will recall their favorite team was once involved in a similar blockbuster.

According to MLB’s Sarah Langs, the last time a first-place team traded a player who had been an All-Star for them that year was 2014, when the Oakland A’s sent Yoenis Céspedes to the Red Sox for Jon Lester.

We all know the story with Lester. Red Sox ownership shamefully low-balled their ace to spoil any chance of an extension. With their season slipping away, Boston was forced to deal the lefty at the trade deadline.

As painful as it was to part with Lester, the Red Sox felt it was necessary to get value for him before he hit free agency. While they approached Lester with a much more reasonable offer after that 2014 season, giving him a taste of life with another team slammed the door shut on any potential hometown discount. Lester signed a lucrative deal with the Chicago Cubs that Boston wasn’t willing to top.

The Red Sox put themselves in the unenviable position that led to losing Lester. It’s no wonder why they traded him under the circumstances. The surprising aspect of the trade was Oakland’s willingness to include Céspedes, who made his first All-Star appearance that season after hitting .256 with a .767 OPS and 17 home runs in 101 games with the A’s prior to the trade.

Oakland was receiving the legitimate ace they needed to lead their rotation into the postseason but they had to sacrifice an All-Star to get him. It was an unconventional approach to the deadline but it worked in terms of filling Oakland’s biggest need.

The A’s had a two-game lead over the Los Angeles Angels at the end of July 2014. Oakland ended up finishing 10 games behind the surging Angels and settling for an appearance in the Wild Card game, which they lost to the Kansas City Royals.

Lester was brilliant for the A’s down the stretch and finished fourth on the AL Cy Young ballot. Unfortunately, the postseason track record he was coveted for wasn’t on display that year. Lester was shelled for six runs in the Wild Card game, which Oakland lost in extra innings. His final appearance with the A’s was a disaster but the trade was an overall success considering his strong finish to the regular season. Oakland probably wouldn’t have fended off the Seattle Mariners, who finished only a game behind them in the Wild Card race, without Lester.

As for Céspedes, his power declined despite the move to a hitter-friendly environment, finishing with only five home runs in 51 games with the Red Sox. His production was otherwise fairly consistent with what made him an All-Star in Oakland but his brief audition failed to convince the Red Sox that he was a keeper. Boston soured on his low on-base percentage and disappointing power. Céspedes had a cannon for an arm but his defense in front of Fenway’s towering green wall was otherwise erratic.

The Red Sox flipped Céspedes to the Detroit Tigers after the season for Rick Porcello. While he had an up-and-down tenure in Boston, Porcello earned a Cy Young award in 2016 and he played an important role in the World Series championship run in 2018.

Flash forward to eight years later and the Brewers find themselves in a similar situation where they are attempting to both buy and sell. Milwaukee has a three-game lead in the NL Central but they were still willing to part with one of their most valuable assets.

The small-market Brewers weren’t eager to pay Hader when his salary bumps up to around $16 million in his final year of arbitration and it’s long been expected that they wouldn’t be able to retain him when he reaches free agency at the end of the 2023 season. Now was the time to deal him in order to get the best haul in return. Milwaukee firmly believes that Devin Williams can fill the ninth inning void and getting the proven veteran Rogers back in the deal provides some insurance for the closer role.

The Brewers are attempting to dance on the tightrope of securing their future while remaining competitive this season. Boston once made a similar decision, dealing a star they feared was on his way out of town anyway while acquiring a player they thought would keep them competitive that season and beyond. It didn’t work out for the 2014 Red Sox but the addition of Porcello eventually served as a solid consolation prize for losing Lester.

It remains to be seen if the Brewers will regret trading Hader. It’s hard to make a case for Milwaukee’s 2022 championship aspirations improving from this deal but at least they remain a contender who has added some enticing pieces to their future.