29. RHP Jeremy Jeffress
The road through the majors has been a long and complicated one for Jeremy Jeffress, starting and ending with Milwaukee with all kinds of stops in between. While his results for other teams have been mixed, Jeffress always seemed to be at home when he was with the Brewers.
2010: 0.0 WAR
Total WAR: 4.0
Jeffress was a first round pick of the Brewers back in 2006. He spent the next five years trying to work his way to the majors. Making that journey much more difficult, Jeffress tested positive three times for a “drug of abuse,” which earned him two suspensions totaling 150 games. Despite the adversity, he made his debut in 2010, pitching 10 games in relief and finishing that year with a 2.70 ERA.
During that offseason, Jeffress was traded away to the Royals in a large package that famously netted the Brewers Zack Greinke and Yuniesky Betancourt for their 2011 playoff run. He spent two years in Kansas City before being designated for assignment in the offseason and being claimed by the Blue Jays. Toronto kept him around for just over a year, but eventually they also DFA’d him just three games into the 2014 season.
Jeffress went unclaimed this time and elected free agency instead of reporting to the minor leagues for Toronto. At this point the Brewers saw an opportunity to give Jeffress a second chance and signed him to a minor league contract. A return to Milwaukee was just what he needed because when he was called up to the majors in July, he went on to give up just six earned runs in 29 appearances, good for a 1.88 ERA.
The right-hander was impressive the following year as well. In 2015 he appeared in 72 games, second most of his career, and going 5-0 with a 2.65 ERA. Jeffress was on pace for a third straight solid year for the Crew, compiling an even lower 2.22 ERA through the first 47 games of 2016 and even adding 27 saves as the team’s primary closer. Unfortunately that earned him a second trade away from Milwaukee, this time with Jonathan Lucroy to the Rangers at the trade deadline for prospects.
Mixed results with Texas ended up having them trade him right back to the Brewers at the 2017 trade deadline for a third stint in Milwaukee. He finished the year well enough with the Brewers, ending up with a 3.65 ERA in 22 games to end the season. But that was just a precursor to what would be a very special following year.
As part of a deadly trio at the back end of Milwaukee’s bullpen that included Corey Knebel and Josh Hader, Jeffress had by far the best year of his career in 2018. He set career bests in appearances (73), ERA (1.29), WHIP (0.991), and strikeouts (89). The performance also earned him the only All-Star appearance of his career to date.
Unfortunately things took a turn for the worse last season as Jeffress suffered his first poor season with the Brewers. Hampered by an injury that caused him to miss the start of the season, Jeffress never quite got into his groove and escalated to a 5.02 ERA. He found himself on the Injured List again in August and with the Brewers trying to secure a playoff spot, he was designated for assignment and is a free agent.
Jeffress has had successful tenures in Milwaukee, and it appears to be the place he’s most comfortable. With his success pitching in some big games and over multiple seasons, Jeffress comes in at No. 29 on our list.