As former American League cohorts with the Yankees until 1998, and now members of the NL Central, the Brewers have a bit of a limited history with the Bombers. The Brewers franchise entered Major League Baseball for the 1969 season as the Seattle Pilots, before moving to Milwaukee under their current name the following season.
The Yankees and Brewers actually met in the first iteration of the Division Series during the shortened 1981 season, with the Yankees winning the series, 3-2. Since their inception, they have made 19 trades with the Yankees, mostly as low-impact moves on both sides, but that isn’t to say they were meaningless. Some of those deals helped fuel historic playoff runs, or led to other massive trades down the line. Let’s take a look at some of the highlights in their history as trade partners.
August 23, 1996: The Yankees trade Bob Wickman and Gerald Williams to the Brewers for a player to be named later, Pat Listach and Graeme Lloyd. The Brewers sent Ricky Bones (August 29, 1996) to the New York Yankees to complete the trade. Pat Listach returned to original team on October 2, 1996.
This is not quite the blockbuster we might see from other teams in this series, but it was impactful in its own right. We’ll start with those who left the Bronx in this deal. Williams was a role player who only appeared sparingly in his first four seasons with the Yankees. He had a nice-enough start in ‘96 so the Yankees capitalized and moved him in this deal. He struggled mightily in his season-and-a-half in Milwaukee, and would only have one season with a 100 OPS+ or better for the rest of his 14-year career. Wickman, however, paid dividends for the Brew Crew. In 1997 the righty had a 2.73 ERA in nearly 100 innings of relief. He shifted to a closer role the following year, and had a very nice career in that spot, racking up 267 saves before retiring over a decade after the trade.
The headline of the Yankees’ return in this deal was left-handed Australian-born reliever Graeme Lloyd, since Listach had an injury that led to him getting returned to Milwaukee. The lefty-specialist was only with the Yanks for parts of three seasons, but picked good ones to be around. He rebounded from an absolutely awful stretch run in ‘96 to become a true weapon for the championship run in October. In total, Lloyd worked a 129 ERA+ in his time with the Yankees, which included a stingy 1.67 ERA in the magical ‘98 season.
Most notable in his tenure however, was Lloyd’s excellence in the postseason. From ‘96-’98 he appeared 13 times in the playoffs, completing eight innings, giving up just two hits and no runs, helping the Bombers take home a pair of rings in that time.
After his successful run, Lloyd was also used as part of the deal to bring Roger Clemens to the Bronx. Even on his way out, the lefty was helping the Yankees win games.
September 1, 2019: The Brewers trade Brenny Escanio and international bonus slot money to the Yankees for J.P. Feyereisen.
Just like the “best deal” was not some slam dunk win, the worst deal is no catastrophe. The Yankees received a then-16-year-old Escanio in this deal, and the jury is still mostly out on what the Yankees have. He is still just 21, but has not appeared any higher than A-ball, and has not performed all that convincingly in the minors thus far.
New York sent away 26-year-old J.P. Feyereisen to the Brewers. He also had yet to appear in the bigs, but rose the ranks quickly. He had a cup of coffee with Milwaukee in 2020, but broke out in ‘21. After a solid 19.1 innings, the Brewers traded him again to the Rays, where he was unlocked even further. He managed a 2.45 ERA in his final 36.2 innings. Then, in 2022, Feyereisen pitched 24.1 innings for Tampa Bay and did not allow a single earned run, along with his career-best K rate and slashed walk rate. He missed all of 2023 with shoulder surgery, so how he fully pans out remains to be seen.
Most Overlooked Trade
July 13, 2017: The Yankees trade Tyler Webb to the Brewers for Garrett Cooper.
This one takes some squinting (as Matt did the other day with Pat Dobson), but perhaps that’s why it fits the overlooked bill. Cooper was a 26-year-old first baseman who had not played in the major leagues, but he was important nonetheless. He did a nice job in his brief stint in 2017 for the Yankees (113 OPS+ in 45 PA), but it’s what he did after that takes the cake.
That offseason, Cooper was traded as part of a package to the Marlins, in the deal that brought in Michael King.
On his own, of course, he was mostly excellent with the Yankees, crafting a 3.38 ERA and 3.34 FIP in parts of five seasons. More recently, King was dealt as the headliner from the Yankees to the Padres in the Juan Soto blockbuster. It takes some digging, but we can all partially thank Tyler Webb and Garrett Cooper for Juan Soto’s arrival in the Bronx.
May 25, 2018. The Yankees trade Erik Kratz to the Milwaukee Brewers for a player to be named later. The Brewers sent Wendell Rijo (minors) (June 16, 2018) to the Yankees to complete the trade.
So many trades could be seen as weird in any number of ways. The oddness of this one is headlined by yet another Erik Kratz uniform change. This was the 15th organization change for the journeyman backup catcher, though it would not be the end of his time in pinstripes.
He did not debut until his age-30 season, but across 11 years Kratzy played for nine big league teams, and was not afraid to return to old friends from time to time. Kratz became a cult hero in Milwaukee during their run to the NLCS that October, and he later reunited with the Yankees in 2020, where he had a nice .760 OPS in 30 plate appearances (the last gasp of his career).
Other Trades of Note
June 15, 1968: The Seattle Pilots purchased Jim Bouton from the Yankees for $20,000 (but Yankees paid $8,000 of his 1968 salary).