As aging All-Stars get to the point in their career where their long-term contract prospects have dried up, but they're still producing respectable numbers, their opportunities lend more toward the short-term, hired gun variety. In Dave Winfield's case, it was also an opportunity to play in front of his hometown. Dave was born and raised in St. Paul, Minnesota, and was a star baseball and basketball player for the University of Minnesota Golden Gophers, so it was an easy decision for him to sign with the Twins, joining a roster that included another future Hall of Famer, Kirby Puckett.
Winfield signed with the Minnesota Twins in mid-December 1992. By that time, the first series of all the main 1993 sets had already been printed and were already being shipped. As a result, Winfield would appear as a Blue Jay for the first couple months of the baseball season. However, given the move to multiple series and the expansion of sets issued around the start of the season, there were a lot of non-update type cards to feature Dave in his new duds. I'll just take these alphabetically.
1993 Bowman shows him in broad daylight, so it is very likely a spring training photo.
1993 Donruss was interesting as Winfield appeared in the Elite insert set in packs. As in previous years, there was a mail-in offer for jumbo versions of the Elite cards. In a twist, Winfield would be depicted as a Blue Jay on the version found in packs and a Twin in the jumbo version.
In another bit of quirkyness from the folks at Leaf, Inc., Winfield was featured in the Gallery of Stars set that was inserted into packs of 1993 Triple Play, but he didn't actually have a card in the 1993 Triple Play set.
For their base set, Fleer didn't follow the crowd, and continued to issue their yearly set in one series. However, possibly in an attempt to keep up, they did expand their yearly update set in 1993, rebranding it "Fleer Final Edition". A few years later, they would begin issuing their update set in packs. Clearly another spring training photo as he's in home whites, but outside in the sunlight.
For the first time since, well, ever, O-Pee-Chee issued a fresh design for their 1993 baseball set. It was wrapped up early enough that Dave was still depicted as a Blue Jay, but they did manage to tack on the "Now with Twins 12-17-92" note.
I was reasonably sure Pinnacle's Select brand, their mid-range set, was a mid-year release, but they still had Winfield as a Blue Jay. They didn't catch up until the Select Rookies/Traded set.
Topps, while having made the transition back to multi-series releases in 1993, still pushed them both out the door too quickly to capture the team change and didn't feature Dave in Twinkie duds until the yearly Traded set. Interestingly the photo here is clearly from the same game, and possibly the same at bat as the Fleer Final Edition card judging from the fan in black and the knee of the fan in white just over Dave's left shoulder.
All of the other base sets in 1993 were issued late enough in the year that they managed to capture Dave's change of scenery in either their respective main releases or second series. Somewhat disappointly, Dave would not finish up his career with the hometown team. After a decent 1993 in Minnesota, which saw him collect his 3,000th hit and 500th double, he had a relatively slow 1994 and spent part of it on the 15-day DL in July.
By August, he would be sold to Cleveland (effectively for the price of a dinner between the Twins and Indians executives), who were atop the AL Central Division, and making bid for the playoffs. Unfortunately for all parties involved, the players' strike would cut the season short and the year would end with Winfield becoming a free agent, never getting the chance to play for the pennant contending Indians down the stretch. Still looking for that bit of veteran experience for the 1995 season, Cleveland would sign Winfield for his final year. We'll save that for Part 5.