Josh Hader got a huge deal from the Astros. Here's how similar reliever mega-contracts have worked out

Josh Hader just became a very rich man while playing a position that rarely sees such paydays.

The left-handed closer reportedly agreed to a five-year, $95 million deal with the Houston Astros on Friday, the largest present-day value contract for a relief pitcher in baseball history by nature of the deferrals in Edwin Diaz's $102 million deal. Such contracts for relievers are notoriously risky, with teams usually preferring to spend lightly and hope they find a breakout player, rather than opening the checkbook.

Relief pitching is a notoriously volatile endeavor in which a steady veteran can suddenly become unplayable — even Hader had a version of that when he posted a 7.31 ERA in his first half-season with the San Diego Padres. It is only the elites who earn contracts analogous to those of quality starting pitchers.

Let's take a look at how some of those reliever deals have worked out.

Largest reliever contracts in MLB history

With this list, we're including only pitchers who were signed to be relievers.

Edwin Diaz, New York Mets: $102 million, five years

The Mets acquired Diaz with great fanfare as part of the Robinson Canó trade in 2018. It was a bumpy ride the next few years, with Diaz posting a 5.59 ERA in his first season in Queens. He picked things up when it counted, though, dropping a career-high 1.31 ERA in his walk year while becoming a sensation with his "Narco" entrance. In the end, Mets owner Steve Cohen refused to let Diaz walk and paid dearly in November 2022 to keep him on the would-be contender.

Do the Mets regret it? At this point, the answer has to be yes, but we're also only one year in. Diaz missed the first season of his contract after infamously tearing his patellar tendon while celebrating a World Baseball Classic save with his Puerto Rican teammates. He will enter 2024 with plenty to prove, even if the Mets as a whole have much lower expectations.

Aroldis Chapman, New York Yankees: $86 million, five years

Chapman had an eventful walk year, and "eventful" isn't the best adjective when it comes to relievers. The flamethrower began 2016 with a 30-game suspension for violating MLB's domestic violence policy, pitched well upon his return, got traded to the Chicago Cubs, pitched even better the rest of the regular season and struggled in the postseason even as his team broke the curse. He then became a boomerang signing for the Yankees, returning to the team in December 2016, mere months after they traded him.

Do the Yankees regret it? Probably not. Chapman's numbers were a step back from his earlier days, but a 2.82 ERA over the course of five years would've met most reasonable expectations. Less solid was Chapman's 4.46 ERA in his final year with the Yankees, which he got by leveraging his third-year opt-out into a one-year extension.

Kenley Jansen, Los Angeles Dodgers: $80 million, five years

Jansen entered the market as the Dodgers' all-time leader in saves after a solid five-plus years of locking down the ninth inning with his signature cutter. He chose to stay with the Dodgers in December 2016, despite reported richer offers elsewhere, but it's also not likely Los Angeles got a significant discount.

Do the Dodgers regret it? Absolutely not. Jansen had his bumps like any reliever, but over the course of the contract, he was the closer on three teams that advanced to the World Series. With trustworthy pitchers at a premium deep in the postseason, it's difficult to imagine the team thought Jansen's cost was too high.

Mark Melancon, San Francisco Giants: $62 million, four years

Another cutter artist, Melancon had something of a journeyman career before striking gold in San Francisco. He saw time with three teams before becoming an All-Star with the Pittsburgh Pirates, then got traded to the Washington Nationals as a rental in 2016. That December, the Giants clearly needed a closer; they got one in Melancon.

Do the Giants regret it? They should. Melancon struggled to a 4.50 ERA in his first season, got demoted from the closer role in favor of Sam Dyson and then Will Smith, and was eventually traded to the Atlanta Braves.

Raisel Iglesias, Los Angeles Angels: $58 million, four years

Iglesias was a longtime trade candidate during his time as the Cincinnati Reds' closer, and he finally heard his name called after the 2020 season, moving to the Angels. His first season in Anaheim was a success, as he recorded a 2.57 ERA and a career-best 37.7% strikeout rate in 70 innings and received Cy Young votes. The Angels liked him enough to bring him back as a free agent in December 2021.

Do the Angels regret it? This one took a few turns. Iglesias had a 4.91 ERA as of June 5, 2022, pulled himself together over the next two months, then got traded to the Atlanta Braves in a salary dump. He began his Atlanta tenure as a setup man and eventually earned the job as the team's closer. Clearly, the Angels regretted his contract, but with two years left on the deal, the Braves probably don't.

Liam Hendriks, Chicago White Sox: $54 million, three years

After being designated for assignment four times in his career, the Australian landed with the Oakland Athletics and morphed into an All-Star closer, becoming a fan favorite in the process. He was one of the top relievers in baseball when he signed with Chicago in January 2021.

Do the White Sox regret it? They really shouldn't. Hendriks was an All-Star his first two years in Chicago and threw 71 innings (across 69 appearances) for a division champion in 2021. Sadly, his success hit a speedbump in 2023, when he was diagnosed with non-Hodgkin lymphoma. His return to baseball in May was inspiring, but he wound up needing Tommy John surgery and missed most of the season.

Wade Davis, Colorado Rockies: $52 million, three years

Davis was arguably the best reliever in baseball circa 2015, going from setup man to closer in back-to-back pennant runs for the Kansas City Royals. He kept that success going after a trade to the Chicago Cubs and joined Colorado in December 2017 having posted a 1.45 ERA over the previous four seasons, though there were some concerning peripheral steps back in 2017.

Do the Rockies regret it? This was such a disaster that the Rockies front office probably has a neon sign next to the GM's desk that says "Never pay a reliever." It's important to remember the Davis contract was part of a huge bullpen spending spree that also reeled in Jake McGree and Bryan Shaw. The trio received a combined $106 million from Colorado and collectively posted a 5.89 ERA over the course of their deals. It's almost difficult to take a lesson from a catastrophe such as this. Pay people to pitch at Coors Field at your own peril.

Jonathan Papelbon, Philadelphia Phillies: $50 million, four years

Papelbon earned what was the richest contract in reliever history in November 2011, following seven memorable seasons for the Boston Red Sox, including a 2.33 ERA and 509 strikeouts in 429 1/3 innings. He was brash, and he had his stumbles, but he was a four-time All-Star and World Series champion in Boston.

Do the Phillies regret it? They got what they paid for. Papelbon wound up being nearly as good in Philadelphia, though his arrival coincided with the Phillies' slow descent from their days as a playoff contender. It was a bumpy ride, though, with Papelbon eventually requesting a trade. Ultimately, the team that regretted this contract was the Washington Nationals, who acquired Papelbon at the 2015 trade deadline, and, well, we all remember how that worked out.