5. Jesse Winker - Washington Nationals
There was a time when Jesse Winker looked to be a middle-of-the-order mainstay for years to come. Coming off a 32-double and 24-homer campaign with a .305/.394/.556 slash line for the Cincinnati Reds during the 2021 season. Since then, Winker's career has gotten off track. The following two years saw Winker struggle, putting up an average season with the Seattle Mariners before bottoming out with the Milwaukee Brewers in 2023. The good news is that Winker has seemed to rebound in Washington and has become a possible trade piece for the Nationals.
Through 87 games, Winker has a .267/.383/.437 slash line with 17 doubles and 10 home runs, while his 138 OPS+ is just under the 143 mark he posted in 2021. Even though he is not putting up the same type of season as he did during his final year in Cincinnati, it is definitely close enough that a contending team could take a chance on the soon-to-be free agent.
If the Guardians were to acquire Winker, it would provide a nice offensive boost to their current outfield group. It would also allow them to have another everyday outfielder not named Steven Kwan, something that would help stabilize the lineup on a daily basis rather than having multiple positional timeshares. Of course, this would need to be one of multiple moves made by the front office to solidify their lineup, but it would definitely be one worth making for the Guardians.