Winfield, who came to the Yankees in 1981 and was one of the reasons Steinbrenner thought Reggie Jackson expendable, has yet to play on a World Series winner. He knows what it will take for him to wear the cherished prize.
"I take a size 12," Winfield says.
Steinbrenner has questioned Winfield's ability to lead New York to the world championship. The much publicized run-ins between the two have highlighted some otherwise dull seasons at Yankee Stadium.
Last year Steinbrenner was especially critical of what he claimed was Winfield's failure to produce in the clutch. Winfield claims his year was comparable to the other savior to come to New York -- Gary Carter of the world champion New York Mets.
"Last season they were saying Gary Carter was a candidate for the MVP and he batted what, .250? He had a good season, but you're trying to tell it was that much better than mine?" said Winfield.
For the record, in 1986 Winfield batted .262 with 104 RBI and 24 home runs. Carter batted .255 with with 105 RBI and 24 home runs.
As for hitting in the clutch, Carter had 16 game-winning RBI compared to six for Winfield.
"This season is going to be very interesting," said Winfield, who will be playing on the seventh-year of a 10-year contract. "I know I'll have a good year, but the other things will have to take care of themselves."
The other things center mainly on Steinbrenner, who seems to generate controversy and ill-will among his players.
The owner's latest salvo was fired at Don Mattingly after the Yankee first baseman won his record $1.975 million arbitration hearing. Steinbrenner said for that kind of money he expected the slugger to lead his team to a World Series title.
Such remarks may well cast Winfield in a new role this year -- being overlooked.
Though Steinbrenner later went to lengths to claim he did not want to put added pressure on Mattingly, it's clear the Yankee owner will keep close track of his investment. As Steinbrenner's remarks about Winfield prove, he is not against feuding with his employees in print.
"We're different people and each has to deal with adversity differently," said Winfield of Mattingly. "I will say this, just about every ballplayer I know will do much better when he is supported. You don't wish (negative remarks) on anybody, but for him (Mattingly) to catch up to me he has to live with it for six years."
Then Winfield added with a wide grin: "I think that George appreciates me, he just has a funny way of showing it."
Winfield's average has dropped from .340 in 1984 when he battled with Mattingly for the batting title, to .275 in 1985 to .262 in 1986. He claims that is not a fair measure of his contributions to the Yankees. He points to his defense, which has always been stellar, his speed and his run production.
The 35-year-old outfielder had one item on his agenda before arriving at spring training. he scheduled a stop in Norfolk, Va., to kick off an anti-drug campaign created by the Winfield Foundation.
The program, which is called "Turn it Around," involves community leaders, police, clergy and youth organizations to stop the growing problem of drugs in America.
"I love to go to spring training," he says. "I love it. It'll take a couple of weeks for me to to get it together and the young guys will be trying to get my job, but there is nobody who is going to get it. I may give it up in 10 years when I retire, but until then there isn't anybody who is going to take it.
"It's like I tell my people," said Winfield. "When it's all over and the dust has settled, I'll still be standing."