The Trade That Sent Gary Sheffield Out of Milwaukee Isn't The One You Think

[David Go]

A certain trade led to Gary Sheffield's demise in Milwaukee, and it wasn't the one that sent him to San Diego in 1992.

If Harry Dalton failed to swing a certain 1991 trade, there just may be a seventh retired number occupying the area above the American Family Field scoreboard. Or maybe he’d prefer not to be honored in his least favorite city in America.

Just as Parker's arrival convinced a Brewers legend to stay in Milwaukee, his departure convinced another future legend to want out.

“I hated (Dalton) so much that I wanted to hurt the man,” said Gary Sheffield on the Brewers organization the year after he left Milwaukee.

The trade? Sending Dave Parker to the then-California Angels. The player with his number retired? Gary Sheffield.

Let’s travel to the 1970s in Pittsburgh for a quick history lesson.

The Pirates were perennial contenders in the 12-team National League, winning the 1971 World Series amidst three straight division titles before star outfielder Roberto Clemente’s untimely death.

In the mid-1970s, Dave Parker emerged as the new star in Pittsburgh. In his first full season donning the black-and-yellow in 1975, he rode a .308 batting average and league-leading .541 slugging percentage to a third-place MVP finish, including 25 home runs and 101 RBIs.

Three years later, the Cobra won MVP after winning his second consecutive batting title. He paced the Senior Circuit in slugging, OPS, total bases and WAR. His Pirates took home the Commissioner’s Trophy the following year.

After a circuitous decade in Pittsburgh, Cincinnati and Oakland, Parker hit the market. He’d just won his second World Series while serving as Oakland’s primary designated hitter in 1989.

Meanwhile in Milwaukee, the Brewers hadn’t supplemented their roster in free agency since 1980 and sought to build a core around an aging Yount and Molitor, and a troubled young star in Sheffield.

Parker supplemented the roster, but he also was tasked with guiding the 21-year-old phenom.

“Me and [hitting coach Don] Baylor were there to lead Sheffield to great things,” said Parker in an article released after his autobiography. “The manager, Tom Trebelhorn, was having problems communicating with Gary. The front office placed my locker right next to Gary.”

The 6th overall pick in 1986, Sheffield had a measly .650 OPS in 494 plate appearances across his first two big league seasons. The 1990 season was a different story.

“Every time I came to bat those first two months, I thought about Gary,” said Parker in 2022. “By the end of May, I was batting .335, among the league leaders. Gary was hitting close to .320 and getting on base. The Brewers were battling for first place and our bats were keeping us in the fight.”

Parker earned his final All-Star selection, and Sheffield hit .294 with a .771 OPS and 25 stolen bases in his first full season. Perhaps more impressively, he whiffed just 41 times while drawing 44 free passes.

The former MVP guided the 21-year-old through his off-field antics - nearly refusing to return to the clubhouse after a brief hospital stay and telling the media he wanted to play shortstop in ‘91 before his manager.

But the Brewers entered 1991 with a different problem - they had two DHs in Parker and Molitor.

They waited until spring training to deal one of the future Hall of Famers, ultimately sending Parker to California for Dante Bichette.

“This was all about Selig reneging on the spiritual deal we had for mentoring Gary,” Parker recalled a few years ago. “Sheff flipped the f— out after he heard the news. The relationship between him and the Brewers went to pieces from there. Sheff was upset the whole season.”

The fractured relationship contributed to a 100-point drop in his average and a season where he accumulated minus-1.3 WAR. The Brewers elected to send the conflicted wunderkind to San Diego after the season.

“Nothing went right there, nothing at all,” Sheffield told then-LA Times reporter Bob Nightengale at the time of the trade. “There were always rumors about me, always something. After my rookie year, I knew I wouldn’t fit in Milwaukee.

“I pretty much used the press just to get out of the organization. That was the tactic I used. I guess it worked.

“But I know it also damaged my reputation.”

Despite the trade occurring less than two weeks before the season opener, Sheffield wasted no time acclimating to his new home in Southern California.

The Tampa native paced MLB in total bases, won the NL batting title and clubbed 33 home runs and 100 RBIs, finishing second in slugging percentage and OPS to Barry Bonds. His remarkable production earned him a third-place finish in MVP voting.

“The Brewers brought out the hate in me. . . . I was a crazy man,” Sheffield told Nightengale. “I hated everything about that place. I didn’t even want to come to the ballpark. If I missed a ball or something, so what?

“If the official scorer gave me an error that I didn’t think was an error, I’d say, ‘OK, here’s a real error,’ and I’d throw the next ball into the stands on purpose. I did it all.”

The future star went on to club 509 home runs and steal 253 bases - one of just four ever to reach both marks. The others: Barry Bonds, Alex Rodriguez and Willie Mays. Despite 9 All-Star selections, 5 Silver Sluggers and a batting title, he failed to gain the 75% of the vote needed for Hall of Fame election.

The lone bright spot in his troubling four-year tenure with the Brewers was when Parker was at his side. Perhaps had he stayed, a different story would be written on Sheffield’s prolific career.

Note: Quotes were drawn from and attributed to the following sources

• NO MORE TROUBLE BREWING : New Padre Gary Sheffield Says He Left His Troubles in Milwaukee, LA Times / Bob Nightengale
• A Dugout From Hell : Padres’ Sheffield Says He Nearly Quit Baseball After Stint With Brewers, LA Times / Bob Nightengale
• Exclusive Missing Chapters From Baseball Legend Dave Parker’s Memoir | Cobra: A Life of Baseball and Brotherhood (Part 3), MLB Bro / Dave Parker & Dave Jordan

View full article

[Brock Beauchamp]

This is such an informative way of looking at the Sheffield debacle, an angle I’ve never heard before.

[jay87shot]

Love this, I never got why Molitor transition to DH so soon. Was there an injury or was he just never a great fielder in the 1st place. It was a hair before my time.

I personally am glad they got rid of Shef, he was always a moron anyway.

[Michael Trzinski]

Nice piece, @David Go!

[Thurston Fluff]

4 hours ago, Brock Beauchamp said:

This is such an informative way of looking at the Sheffield debacle, an angle I’ve never heard before.

He couldn't stay healthy.

The article is nice and all but it doesn't absolve the fact Sheffield was the problem. Had the Brewers trade Molitor to keep Parker simply because Sheffield wanted him he'd have been the most hated man in Milwaukee. I seriously doubt that would have helped his productivity. Not to mention it's just plain old bad management to allow one player to dictate who stays and who goes.

[Snoebird]

9 hours ago, jay87shot said:

Love this, I never got why Molitor transition to DH so soon. Was there an injury or was he just never a great fielder in the 1st place. It was a hair before my time.

I personally am glad they got rid of Shef, he was always a moron anyway.

Molitor missed 492 games -- two broken bones, elbow and hamstring injuries plus a shoulder impingement -- in his first 10 seasons and was the first non-pitcher to undergo Tommy John surgery. But he always had those quick wrists at the plate, and had a great late career thanks to his move to DH. 

[jam]

"I feel that there is some amazing talent in Wisconsin and/or people who left Wisconsin and went on to do some amazing things. However, it’s our history to not give Black people credit" (https://shepherdexpress.com/culture/visual-art/new-mural-celebrates-wisconsins-black-athletes/) (https://www.artsbyaya.com/). This article is important reflection work and perhaps raises uncomfortable questions.

[Brock Beauchamp]

3 hours ago, jam said:

"I feel that there is some amazing talent in Wisconsin and/or people who left Wisconsin and went on to do some amazing things. However, it’s our history to not give Black people credit" (https://shepherdexpress.com/culture/visual-art/new-mural-celebrates-wisconsins-black-athletes/) (https://www.artsbyaya.com/). This article is important reflection work and perhaps raises uncomfortable questions.

Welcome to Brewer Fanatic!

[David Go]

On 2/1/2025 at 2:35 PM, Thurston Fluff said:

He couldn't stay healthy.

The article is nice and all but it doesn't absolve the fact Sheffield was the problem. Had the Brewers trade Molitor to keep Parker simply because Sheffield wanted him he'd have been the most hated man in Milwaukee. I seriously doubt that would have helped his productivity. Not to mention it's just plain old bad management to allow one player to dictate who stays and who goes.

I don't disagree that it's a problem that Sheffield did what he did - just presenting that maybe things go differently if they kept Parker.

[David Go]

On 2/1/2025 at 10:58 AM, jay87shot said:

Love this, I never got why Molitor transition to DH so soon. Was there an injury or was he just never a great fielder in the 1st place. It was a hair before my time.

I personally am glad they got rid of Shef, he was always a moron anyway.

Molitor had shoulder surgery that relegated him to 1B/DH after the 1990 season.

[David Go]

On 2/1/2025 at 11:26 AM, Michael Trzinski said:

Nice piece, @David Go!

Thanks, Michael!

[Outlander]

1 hour ago, David Go said:

I don't disagree that it's a problem that Sheffield did what he did - just presenting that maybe things go differently if they kept Parker.

I doubt it, Parker was washed up in 1991 and likely would not have ended well with him, could only imagine how bad it would have been if they traded Molitor in 1991. It was doomed to fail no matter which route was chosen with Parker. 

[Thurston Fluff]

2 hours ago, David Go said:

I don't disagree that it's a problem that Sheffield did what he did - just presenting that maybe things go differently if they kept Parker.

Maybe but Sheffield wanted the big city and bright lights he was never going to get here. He wasn't happy he got drafted by Milwaukee to begin with. It's hard to blame one move for something that started off poorly. At most I'd say it was the final straw as opposed to the prime factor.

[Jopal78]

12 hours ago, Thurston Fluff said:

Maybe but Sheffield wanted the big city and bright lights he was never going to get here. He wasn't happy he got drafted by Milwaukee to begin with. It's hard to blame one move for something that started off poorly. At most I'd say it was the final straw as opposed to the prime factor.

In my mind, Sheffield has one bad year for the Brewers, one okay year for the Brewers and one year where he was hurt and barely played, then they shipped him out to San Diego. That he had a huge career after leaving Milwaukee never meant anything to me. After ‘92 the Brewers fielded mostly awful teams where Sheffield wouldn’t have made a difference anyhow had he not wore Out his welcome.