Jesse Winker: St. Louis Cardinals (1 year, $3 million)
With the past two years he's had, it seems like one-year, decreasing-in-value contracts are what's in store for Jesse Winker. After a sour depature from the Seattle Mariners, he went to the Brewers with Abraham Toro in a trade for Kolten Wong, a transaction that hasn't really worked out for either party involved, and didn't fare any better in Milwaukee. He only played in 61 games and finished with a pretty shocking final slash line of .199/.320/.247. After a performance like that, it's difficult to say if anyone might want him on their roster at all.
However, for your consideration: the St. Louis Cardinals. After coming off their worst year since 2007, the Cardinals are in disarray. Their .438 season will forever mark the end of Adam Wainwright's career, one of the last years of Paul Goldschmidt's, and the end of Nolan Arenado's 10 season streak of Gold Glove awards. The Cardinals need to do something.
With second baseman Brendan Donovan on the 60-day IL, DH option Nolan Gorman can spend more time there instead of at DH. Same goes for Lars Nootbaar in the outfield, given Dylan Carlson's injury. Then, if they reinstate Willson Contreras as their everyday catcher, that leaves ample opportunities for someone like Winker to slide in as DH. It's unlikely that a relatively low-spending team like the Cardinals will give him as much as he's been making recently ($14 million over the last two years), but Winker is in a very weak position to argue.