If there’s one man who has seen the ups and downs of baseball in the last several years, it’s Anthony Santander.

After being acquired in the Rule 5 Draft by the Orioles in 2016, Santander’s tenure in Baltimore consisted of drudging through multiple 100-loss seasons and sitting in the baseman of the AL East but witnessing a rebuild that led to 100-win seasons and playoff appearances in recent memory. He played a major part in getting the Orioles back to postseason competition, and now he has a chance to reap the rewards of his work during his first free-agency stint this winter. Let’s just say he’ll earn a higher number than the $11.7 million he made last year.

Santander flirted with breakout seasons in the past, but ’24 was the best of his career when it came to run production. In 155 games, he slashed .235/.308/.506 with a .814 OPS, 44 home runs, 102 RBIs and 25 doubles, with the homers and RBIs being career-bests. He was nominated to his first All-Star team and also won his first Silver Slugger award, multiple accolades that won’t hurt to add to his resume this winter.

Santander’s home run total was third-best in the major leagues behind Aaron Judge and Shohei Ohtani, but one thing that might turn some teams away was that his OPS was only .814 despite this. Looking at the home run leaderboard, you’d have to scroll down Pete Alonso at 12 to find the next lowest OPS. His batting average of .235 is the lowest since his 33 games in 2018, and he has only had an OPS north of .800 in one other season (2020). Of course, the other half to that is that he’s in a club with Judge, Ohtani, and Juan Soto (players to hit 40+ homers last season), and there’s no denying that. Teams who need power will and should pay for it. The postseason was a perfect example.

Although a switch hitter, Santander didn’t have a drastic difference between slash lines on either side of the plate. He hit much better on the road than he did at Camden Yards – a 110-point OPS difference, to be exact – which may be a factor when choosing his next destination. That left field wall might’ve been pushed back too much. His month-to-month splits stayed relatively consistent, but his best months were June (13 homers, 26 RBIs) and July (.303 BA, .987 OPS).

Santander matches the profile of a heart-of-the-order power bat, and the Blue Jays haven’t stuck a consistent cleanup hitter behind Vladimir Guerrero Jr. since Teoscar Hernández was in Toronto. Santander was most productive last season when hitting in the 4th or 5th spot of Baltimore’s order, but it helped that he was surrounded by top-notch hitters in Gunnar Henderson and Adley Rutschman. What separates Santander from many other free-agent power hitters is that he can swing it from both sides of the batter’s box, which could eliminate the need to platoon him given he’s at least somewhat effective from both sides of the plate. That’s a luxury that the Blue Jays haven’t had since Justin Smoak roamed the Rogers Centre infield.

With Santander spending his first eight seasons in Baltimore, he has amassed 226 career games against the Yankees, Rays, and Red Sox. However, he doesn’t have any eye-popping splits at any of those opposing ballparks, with a .248 batting average and .806 OPS at Fenway Park being the best of that group. He had also struggled in the Rogers Centre up until last season when he hit four home runs and seven RBIs there.

Signing a power bat hasn’t been one of Ross Atkins’s strengths during his tenure in Toronto unless you’re willing to categorize Marcus Semien as such. Outside of that, it’s been Travis Shaw, Brandon Belt, and Justin Turner, all of which were one-year deals for veterans on the back end of their careers or looking for a last kick at the can. So, while the fit may be there for Santander and the Blue Jays, it doesn’t fit the mould of how Atkins has acquired bats in recent seasons.

Again, Santander would check multiple boxes for the Blue Jays, but the price that Santander and his representation will be seeking will be an interesting development. Like Sportsnet’s Ben Nicholson-Smith pointed out earlier this offseason, the timing of Santander’s 40-home run campaign was perfect for a contract season but there’s a chance that his best years are behind him, presenting a “buyer beware” scenario for the 30-year-old. Of course, this is the case with several free agents year in and year out; contracts are an investment of what teams think you’ve earned and what you still can be, but no one can tell the future.

Spotrac currently projects Santander will earn a 5-year deal at $88.6 million (~$17 million AAV). Interestingly enough, Santander was extended a $21.05 million qualifying offer from Baltimore, but coming off of a career season, there may be other teams willing to offer stability with a multi-year deal.

Despite trading away some of their younger talent last year, the Orioles still have a relatively deep prospect pool, further lessening the odds of Santander re-signing on a long-term deal with them. On the list of their needs, it would make sense financially for them to acquire starting pitching or bullpen arms. The Royals and Nationals are a pair of upcoming teams who would benefit from adding Santander to their lineup and have money to spend, and the Red Sox could also be a good fit given AL East familiarity and Tyler O’Neill’s impending departure.