For the third consecutive entry into the free agency series, another elite left-handed reliever is due to be covered. For better or for worse, the Yankees made another splash in the offseason following the 2018 season from a free agent class that featured far more generational talent than the usual crop.
Zack Britton, in all fairness, was not all that far removed from one of the great pitching performances in modern baseball history. The perception of his deal may not be entirely fair, as it wouldn’t
be right to compare his overall value to someone like Bryce Harper or Manny Machado, but on the whole, Britton was quite good for the Yankees. Big-money deals on relief pitching can feel like a letdown when there are A-list free agents available on the market, but Britton was elite for a long stretch, some of which the Yankees were able to enjoy.
Zack Britton
Signing Date: January 11, 2019
Contract: Three years, $39 million
Britton, a 6-foot-1 left-hander, was originally drafted in the third round of the 2006 amateur draft by the Orioles. He would remain with that organization for over a decade, and see a level of success at times that few other pitchers in the history of the sport enjoyed.
He initially came up as a starter, pitching over 150 innings across 28 starts in his 2011 rookie campaign. Over the next couple of seasons, he was only able to make 11 and seven starts for Baltimore, respectively. Unfortunately for the O’s and their lefty, it was an unconvincing stretch on the bump, as he managed an ERA approaching five across those three years.
For the 2014 season, Britton was moved to the bullpen. As a result, he almost instantly became one of baseball’s most dominant forces on the mound. He pitched in a career-high 71 games, racked up 37 saves, and managed a stingy 1.65 ERA in over 75 innings of work for Baltimore. A year later, he was just as good in the closer role for the Birds, earning his first All-Star nod in the process. In 2016, his third season coming out of the bullpen, Britton established himself fully as one of the most dominant pitchers on the planet. He had a similar workload, 67 innings across 69 innings of work, but he reached an entirely different level after already pitching incredibly well over the last couple of seasons.
In 2016, the 0.54 ERA he posted still stands as the lowest figure by a pitcher in MLB history among all to ever throw at least 50 innings in one season. That is no small feat, and it earned him another All-Star selection, as well as a fourth-place finish in the Cy Young voting (in a weaker year for candidates, he may have had a legitimate case for the award). Britton was perfect in save opportunities, closing down all 47 chances that Buck Showalter gave him. It would take some squinting, but there is an avenue where you could call that season one of the great pitching performances in baseball history.
It’s just a shame that Showalter’s outdated thoughts on closer usage meant that Britton inexplicably didn’t throw a single pitch during Baltimore’s Wild Card Game loss to the Blue Jays. Held out for a save opportunity that never came, he could only watch as Edwin Encarnación took Ubaldo Jiménez deep to walk it off in the 11th.
Britton missed some time in 2017, and was not quite at the same level in his 39.1 innings, though he was still very solid. The following season was mostly the same for Britton with Baltimore in the first half, and he was eventually sent to the Yankees in a rental trade that saw New York deal three prospects but none of particular note. He worked 25 games with the Yankees that season, maintaining a sub-3 ERA in 25 innings, a nice note to hit free agency on.
It was an offseason that carried a lot of hope and potential for plenty of clubs, with the likes of Harper, Machado, and Patrick Corbin headlining the free agent class. They were all players that could have made good fits with the Yankees, though they clearly went a different direction. Instead of any of the top-shelf names, the Yankees re-signed J.A. Happ, made a savvy move in picking up DJ LeMahieu, and in January of 2019, re-upped the services of Zack Britton.
It was a three-year deal, with Britton making $13 million per season, a lot of money for a reliever, surely, but nothing franchise-altering. In his first full season with the club, Britton did his part in making it look like a great deal. The lefty pitched over 60 innings, boasting a 1.91 ERA in a high-leverage role in what was one of his best seasons in terms of results. He even did his part in the postseason that year, when the Yankees came to within a game of the World Series. He allowed just one run on two hits across eight innings of work that October.
Although that was his age-31 season, Britton was still in the midst of his prime, and showed minimal signs of slowing down on the mound. Unfortunately for him and the Yankees, however, that year would be his last real chance at a full season of work.
Britton was even better for the shortened 2020 season, but obvious circumstances limited him to just 19 innings of work, albeit very good ones. It was the next season, unfortunately, that his career began to hit the wall. The injury bug had come to bite the Yankees left-hander, as he missed much of that season with injuries in his throwing elbow and his hamstring. His abbreviated work was not up to standards that year either, as he pitched to the tune of an ERA and FIP well north of five, and wrapped up the season with salt in the wound, as he needed Tommy John surgery in September of that year.
A club option was kicked in following the 2020 season, meaning that Britton would remain with the Yankees through 2022, despite the injury trouble. More than a year after his initial shelving, Britton returned for the Yankees in September of ‘22. After three abysmal appearances on the mound, he left a late-season game against his old team, the Orioles, with more elbow discomfort. Surely disappointed in the turn his baseball life had taken, that would be the final action of Britton’s career in the major leagues. He sat out 2023 and then officially retired that November.
Britton’s contract is a difficult one to assess on the whole. Relief pitcher contracts can get funky in general, and he was actually very good for two of the planned three years of their agreement. Despite that, it feels as though his tenure is surrounded by so much disappointment. His career unfortunately ended with a bit of a whimper, and his signing came at a time when fans likely expected a lot more aggression out of the club in terms of spending.
However fair all of that may be, it still feels reasonable to recognize how good of a pitcher Britton was. From 2014-20, Britton’s 1.84 ERA was a distant best in baseball, and the Yankees were able to enjoy two-and-a-half years of that dominant stretch. It may have been an underwhelming deal in the bigger picture, but it’s also hard to deny the value of the signing at the time, and what Britton provided at his best for the Yankees.
See more of the “50 Most Notable Yankees Free Agent Signings in 50 Years” series here.









