Top Ten Deadline Trades In Milwaukee Brewers History

Right now, teams like the Philadelphia Phillies, Los Angeles Dodgers and Milwaukee Brewers are salivating over the thought of adding pitcher Roy Halladay to their starting rotations.

Halladay, the Toronto Blue Jays’ nearly flawless ace, is regarded league-wide as the type of high-impact player that instantly turns any playoff contender into a World Series favorite.

Every team that is interested in a midseason trade for the Doc, however, knows it would take a King’s ransom of elite prospects to even lift Jays’ GM J.P. Ricciardi’s head up from the morning paper.

Trade deadline deals in July often portend whether a team is parading down Main Street in November or their general manager is posting his résumé on Monster.com. Last season, it was the Brewers that cannon-balled into the trade pool, pulling off arguably the most impactful deal in baseball history, and landing a player who erased over a quarter-century’s worth of baseball irrelevance in 4 months.

But long before they welcomed their 6’7”, 300-pound knight in shining armor to the City of Beer and Cheese, the Brewers made other  important trades that significantly altered the course of their franchise.

Whether they can and will do it again with Halladay remains to be seen. Until then here’s a look at the top ten most influential deals in Brewers franchise history.

10. June 15, 1977: Brewers trade two minor-leaguers, Dick O'Keefe and Garry Pyka, to Cincinnati in exchange for pitcher Mike Caldwell.

Considering what the Brewers gave up—a Google search for “Dick O’Keefe” brings up the statistics of a 1940s NBA player of the same name, and Pyka hit .239 in three minor league seasons—the deal was a highway robbery for Milwaukee.

Caldwell went 22-9 in his first season with the Crew and remained a core member of the rotation for almost six more years. For a team with severe pitching deficiencies that still finds a way to let Jeff Suppan lob the ball toward the plate every five days, a Caldwell-type deal would be Christmas in July for Doug Melvin and the Brewers now.

Highway Robbery Deal Runner-Up:

In 1971, the Brewers traded Ray Peters and Pete Koegel to the Phillies for Johnny Briggs. This deal was remarkable for two reasons: First, it allowed the Brewers to purge their organization of two mind-bogglingly awful players while adding a solid starter; and second, because it demonstrated that, even 30 years ago, the Brewers had a singularly deplorable knack for drafting truly abominable pitchers.

A titanic bust, Peters was a first round pick whose major league career lasted about a week. Spending all of two innings on the mound, he went 0-2 with a 31.50 ERA (Derrick Turnbow-esque numbers, to be certain) and Koegel batted .174 over 3 seasons. Briggs, for his part, had a respectable run with the Brewers, averaging around .260 and 20 home runs in four seasons.)

9. June 6, 1983: Brewers trade Gorman Thomas, Ernie Camacho and Jamie Easterly to the Cleveland Indians for Rick Manning and Rick Waits.

Despite being relatively inconsequential, Brewers fans regarded this trade as indefensible. “Stormin’ Gorman” Thomas’ most mash-tastic years were certainly behind him by 1983, but he was still one of the most beloved Brewers of all time. A fixture in the middle of the order for some of the Brewers’ best teams in the early ‘80s, Thomas hit more home runs between 1978 and 1982 than any other player in the American League. The deal that exchanged him, along with the serviceable Camacho and Easterly, for Manning and Waits was extremely controversial among Brewers fans at the time.

Still, Manning had many momentous accomplishments, including catching the final out of Len Barker’s perfect game (though it wasn’t with the Brewers) and popularizing the legendary “Cheese Head” worn so proudly by Green Bay Packers fans. He will be remembered most, though, for being perhaps the only Brewer ever to be booed at home for a game-winning hit, after his single ended both the game and, more notably, Paul Molitor’s 39-game hitting streak when the fan favorite Molitor on deck.

8. July 31, 1996: Brewers trade Greg Vaughn and Gerald Parent to San Diego for Bryce Florie, Ron Villone and Marc Newfield.        

Floundering in last place, this was the definition of a trade deadline sale, and it was a bad one. The Brewers didn’t get nearly enough for Vaughn, who was an impending free agent the Brewers could not afford to keep. They shipped him west to the Padres where he took his popular, powerful swing and hit 50 home runs in 1998.

Under the circumstances of knowing they wouldn’t be able to retain the big slugger, this deal would not have been nearly so bad had the Brewers been able to acquire a couple of batting tees or some Big League Chew from San Diego. Sadly, they had to settle for a few years of mild incompetence from the trio of players they got back.

7. July 29, 2006: Brewers trade outfielders Carlos Lee and Nelson Cruz to the Texas Rangers for pitcher Francisco Cordero, outfielders Kevin Mench and Laynce Nix and minor league left-hander Julian Cordero.

It was initially thought that this deal was mutually and equally beneficial. At the time, it seemed to benefit the Brewers more because Lee, like Vaughn, was going to be an unsignable free agent at season’s end and Cordero was a proven and electrifying closer.

He finished with 16 saves and a 1.69 ERA for the Brewers that season and added 44 with a 2.98 ERA the next year before signing with the Reds. Mench was a mediocre temporary outfielder for Milwaukee, while Nix and Cordero went to the minors and are no longer with the team.

Lee, on the other hand, was, as usual, an offensive “El Caballo” who ultimately left the Rangers to sign with the Astros. Nelson Cruz, though, became an All Star this year for the Rangers and battled Brewers first baseman Prince Fielder in the finals of the Home Run Derby.

Since none of the players the Brewers received are still with the club, and they got nothing but compensation picks for Cordero leaving, it would seem Texas got the better of Milwaukee in this deadline deal.

6. Aug. 31, 1996: Brewers deal Kevin Seitzer to Cleveland for outfielder Jeromy Burnitz.

The Brewers, who were not exactly the pride of the American League at the time, got one of the better offensive players the team has had in the past 20 years in Burnitz, who served as a foundation as the franchise moved to the National League in 1998.

While Seitzer had been planning to retire after the season, Burnitz became a staple of the middle of the Brewers order. He was a .270/30/100 kind of guy that probably prevented the Brewers from challenging the ’62 Mets for futility.

5. May 9, 1961: Milwaukee Braves trade Mel Roach to the Chicago Cubs for Frank Thomas.

Now, had this trade occurred 35 years later than it did and been a deal for Frank “The Big Hurt” Thomas instead of Frank “The Big Donkey” Thomas, it would have been one of the all-time greatest steals in major league history.

Unfortunately, the two-time AL MVP Frank Thomas, who starred for the Chicago White Sox from 1990-2005 and hit more than 500 home runs in his career, had not yet been born when this swap took place.

Still, though, the Brewers hoodwinked the Lovable Losers into trading a guy who would play 16 major league seasons, hitting .266 with 286 career home runs and had the fantastic nickname “The Big Donkey” because of his relatively large (6’3”, 205-pound) body for the era.

You have to wonder what they would have called the later Thomas, who stood 6’5” and 275-pounds. Meanwhile, Roach managed a lifetime .238 batting average with one stolen base and an impressive nine sacrifice hits.

4. July 28, 2000: Brewers trade pitchers Bob Wickman, Jason Bere and Steve Woodard to the Cleveland Indians for first baseman Richie Sexson, Paul Rigdon, Kane Davis and Marco Scutaro.     

Despite being quite fat and so seeming to be a perfect fit in Milwaukee, Wickman was dealt, ultimately becaming the Indians’ all-time saves leader. Nevertheless, this trade was a resounding success for the Brewers.

They ditched Bere and Woodard, two of the first in a long line of pitchers to impel me to swear loudly and hit my head against the wall watching Brewers games, and they reeled in Richie Sexson.

The towering Sexson teamed with Burnitz in the early 2000s to provide some semblance of an offense to a team that featured a wealth of position players no doubt cut from the first “Major League” movie. The 6’8” Sexson was reliably terrific, hitting 45 homers in both 2001 and 2003, to go with 125 and 124 RBI in those years, respectively.

More importantly, in 2003 when the Brewers front office collectively woke up from a two decade-long coma and decided to actually start trying to build the team intelligently, they packaged Sexson for six Arizona Diamondback players who then netted more young players, themselves, establishing the groundwork and financial flexibility that has contributed to Milwaukee’s success the past few years.

3. August 30, 1982: Brewers trade Kevin Bass, Frank DiPino and Mike Madden to the Astros for pitcher Don Sutton.

Sutton spent only 2 ½ seasons with the Brewers, and his numbers aren’t particularly extraordinary, but the Hall of Famer validated the decision to trade for him by beating the Baltimore Orioles 10-2 on the final day of the 1982 season to win the AL East title for the Crew.

He was a dependable starter and a magnificent clutch and playoff pitcher who helped the Brewers to the World Series in ’82. There’s really no price tag on reaching the Series, and Bass, DiPino and Madden didn’t exactly make the Brewers regret their decision. The Brewers, in turn, traded Sutton to Oakland in 1984 for Ray Burris, Eric Barry and Ed Myers, who all have talented-sounding names.

2. June 15, 1957: Milwaukee Braves trade Danny O'Connell, Ray Crone, and Bobby Thomson to the New York Giants for infielder Red Schoendienst.

A good general rule of thumb is if you weren’t alive for something, and your parents were too young to remember, ask your grandparents.

An even better rule of thumb is that if you ask your 85-year-old grandmother about a specific Milwaukee baseball trade and her face lights up as she exclaims “He was such a great player!” and proceeds to regale you with stories from that 1957 season when Schoendienst hit .309, finished third in the league in MVP voting, and sparked the Braves to the only World Series Championship Milwaukee’s ever had, then that was probably a good baseball move.

Schoendienst was elected to the Hall of Fame in 1989 and Stan Musial said he had “the greatest paid of hands I’ve ever seen.” Despite trading away Bobby Thomson, he of the famous “Shot Heard Round the World” home run, any trade that results in Milwaukee winning the World Series is a good one in my book.

1. July 7, 2008: Brewers trade minor league outfielders Matt LaPorta and Michael Brantley, pitcher Zach Jackson and Rob Bryson to Cleveland for pitcher CC Sabathia.

The easy and obvious choice, though Schoendienst helped the club win a World Series, this was incontrovertibly one of the greatest and most efficacious trades in baseball history.

Sabathia exhilarated the city of Milwaukee immediately upon his arrival, galvanizing a long-tortured fan base and mobilizing a young team into the playoffs for the first time in a quarter century.

The Brewers gave up their top prospect, LaPorta, as well as the highly regarded Brantley, and Jackson, a solid young player, in order to make the deal happen. And boy were they glad they did.

The gargantuan pitcher essentially pitched the Brewers into the playoffs single-handedly, crucially going 11-2 for the Crew with a 2.70 ERA. CC, who informed reporters that he wanted the abbreviation periods dropped from his first name, dazzled Brewers fans by winning his first four starts, three of which were complete games.

He also threw what should have been ruled a no-hitter, and pitched a 4-hitter against the Cubs to win 3–1 in the final game of the season, sending the Brewers to the playoffs for the first time since 1982. He ended the season with 10 complete games, pitched in the playoffs against the heavily-favored Phillies and finished sixth in NL MVP voting, despite only playing in the league for half a season.

Beyond his numbers, Sabathia reinvigorated Milwaukee fans enthusiasm for Brewers baseball and renewed their faith in the organization. The team sold out every home game after Sabathia was acquired, including his very first start with the club, which I attended with a couple friends.

Even though he was far from perfect that day, he electrified the stadium with his pitching, hitting, attitude, class and custom-made XXXL uniform. CC Sabathia was utterly inhuman during his time with the Brewers, and he gave me and the city of Milwaukee memories we won’t soon forget.