The Home Run Derby is set for 8 p.m. ET on ESPN, and in Canada on Sportsnet.
The three former players grew up within a three-mile radius of each other in St. Paul; Winfield on Carroll Avenue, Molitor on Portland Avenue and Morris on Saratoga Street.
Winfield and Molitor are both in the Hall of Fame, while Morris still has the opportunity to be elected by the Veteran's Committee.
Molitor and Winfield are the only duo from the same city to have membership in baseball's 3,000-hit club.
Winfield is slightly older than his hometown friends. He graduated from Central High in 1969, while Morris graduated from Highland Park High in '73 and Molitor was in Cretin High's class of '74.
"I was already playing pro ball by the time Paul and Jack got to high school, but my brother was in St. Paul coaching and teaching, and he would always tell me how well those two were doing," Winfield said on Saturday. "To have three guys grow up so close to each other and do well on a national stage is amazing. We always respected one another, and I'm glad they did so well."
Winfield didn't meet Molitor or Morris until they were all pros. He first faced Morris on April 29, 1981, at Tiger Stadium in Detroit.
"Jack did get me out that first game, but I also hit a home run," Winfield recalls. "I had just come out of a funk I was in through Spring Training, so it was about time for me to hit one. But Jack was always a fierce competitor. He wasn't going to throw me a lollipop just because we were both from St. Paul. He was scowling and doing whatever he needed to do to win."
The first time the trio ever stood together on an All-Star field, they were all smiles. A photographer snapped a photo of the Minnesota natives prior to the 1985 Midsummer Classic at the Metrodome in Minneapolis on July 16 in their American League All-Star uniforms. It was the first time the All-Star Game had been in the Twin Cities in 20 years, and the Metrodome was in just its fourth year of existence. Though Winfield, Morris and Molitor had already been in the big leagues for multiple seasons, it was the first time the three had shared a professional clubhouse.
Morris, who had just won a World Series with the Tigers, started the game for the second of three times in his career, but the National League took a 6-1 win.
Morris made five total All-Star appearances in his career. Molitor made seven, and Winfield 12, appearing in every All-Star Game from 1977-88. That's 24 All-Star appearances for the fellas from St. Paul.
Morris says that photo from 1985 is still one of his favorite pictures, and it is still displayed in a place of honor in Molitor's office in Edina.
On Monday night at Target Field, Winfield, Molitor and Morris will have a chance to take another.
A new format has been installed for this year's Derby, as the five players from each league will receive seven outs instead of the usual 10 in each round. In the first round, the player who hits the most homers in each league will receive an automatic bye to the third round (semifinals). The next two players from each league with the most homers will square off against one another in a head-to-head matchup in the second round, with the two winners advancing to the semifinals against the league's top performer from the first round.
The final round will be a showdown between the AL and NL's best. If necessary, the first tiebreaker would allow the finalists three swings apiece.
If you can't wait for the actual Derby, the MLB.com Home Run Derby mobile game is a good way to immerse yourself in the action immediately, with Target Field serving as the setting. The game is available for download on the Apple App Store and Google Play. New for 2014 is Multiplayer Derby Mode, Achievements and Objectives.