New York Yankees
Could the Twins-Yankees pipeline see some action this winter? Kepler certainly wouldn't be the first outfielder New York has grabbed from the Twins but he might have the highest upside of any player the two teams have traded back-and-forth.
New York has needed corner outfield help for a while, and Kepler would instantly give the Yankees one of the best baseball groups. There were rumors last winter that Kepler might be bound for the Bronx, but nothing came from those talks. A year later the same situation exists, as the Twins might be shopping Kepler to improve the roster elsewhere and the Yankees need outfield help that he can provide.
Kepler's offense was a major question mark last season, but he started to find a groove and turn things on late in the year. Imagine what he was doing for the Twins alongside Aaron Judge and Giancarlo Stanton in the Yankees outfield -- it's not fun to think about if that lineup stands between Minnesota and a World Series next October.
For all that has been said about his offense, having him with the short porch at Yankee Stadium might turn him into a home run monster that might make him another in a long line of Twins players fans regret seeing go.