Jesse Winker may not be a household name compared to some of the other free agents on this list, but he should not be counted out. After all, he is a former first-round pick by the Reds and is still young enough to have some untapped potential. However, it took him a little while before he finally became a regular in the Reds’ lineup, but when it finally happened, he became a main contributor in the process.
In particular, Winker broke out during the 2021 season in which he batted .305 with a .949 OPS, along with 77 runs scored, 32 doubles, 24 home runs and 71 RBI in 110 games played. His career year even earned him his first All-Star nod as a result. However, he has struggled in his following two seasons, including an injury-plagued 2023 year with the Milwaukee Brewers. His batting average fell almost 100 points while his OPS fell between 300-400 points from his 2021 All-Star season.
With the entire offseason to heal up and get back to full health, Winker will be hungry to show his suitors once again that he could be a major contributor in the big leagues. Early on, the Yankees have been linked to him this offseason. With the ability to play both outfield corners and as a designated hitter, Winker would address one of the Jays’ key offseason needs. But given he has a career -23 DRS in left field and a -39 DRS overall in the outfield, having him serving as the left-handed bat replacing Brandon Belt would be the ideal arrangement.