Santander’s cooking, of course, isn’t the only thing that’s come a long way since those unglamorous academy days. Over 13 professional seasons, he’s grown from an unlikely Rule 5 pick to a 44-homer, heart-of-the-order all-star, which is why the Toronto Blue Jays signed him to a $92.5-million, five-year deal as a free agent this winter. Dan Duquette, the former Baltimore Orioles general manager who cleverly lifted Santander out of the Cleveland system in 2016, describes the unlikely ascent this way: “The Orioles purchased Anthony’s contract for $100,000 and the Blue Jays signed him to a contract where he can make $100 million. It’s a long shot, but this one worked out.”

No debate there, and now the Blue Jays, in desperate need of offence after a dismal 74-88 finish in 2024, are counting on the 30-year-old to serve as a power-hitting complement to Vladimir Guerrero Jr. That Santander is a platoon-proof switch-hitter offering long-sought-after left-handed thump makes this an even more natural pairing.

“The fit has always been attractive to us,” says Blue Jays general manager Ross Atkins. “We’ve known the person. His passion for not just playing and competing, but for absolutely doing everything within his control to put himself in the best possible position to be a winning baseball player, has been known for a long time. That has been exceptionally attractive, in addition to the switch-handedness, the position he’s playing and the shape of his offence. He is near as good of a fit as we could have found to help support this lineup.”

Heading into a season with so much at stake for the franchise due to the pending free agencies of cornerstone stars Guerrero and Bo Bichette, Santander has a chance to be the ingredient that helps the Blue Jays rise again in 2025. 

At the same time, Santander’s early years were undermined by surgery to remove a bone spur from his right elbow. He played only 61 games in 2013 with low-A Lake County and a mere 43 while repeating the level the next year. During his third season with the club in 2015, he got back up to 64 games and was much better in them, posting an .801 OPS. That was a springboard into a career-changing 2016 at advanced-A Lynchburg, when he batted .290/.368/.494 with 20 home runs, 42 doubles and 95 RBIs in 128 games. While better health played an obvious role in the progression, Blue Jays first base coach Mark Budzinski, who managed Santander at Lake County in 2014 and then again in Lynchburg two years later, says the development went well beyond that. “He really learned how to take care of his body – what it took on a day-to-day basis,” Budzinski explains. “He established in 2016 a really good routine where he would get to the park early, do a warm-up, do a stretch routine, get all those training-room things taken care. That process, not only from a physical standpoint, but from a mental standpoint, put him in a really good spot to where he was mentally freed up.”

That freedom allowed Santander, 21 at that point, to better utilize his physical tools and leverage all he’d learned, both while playing and sidelined. Budzinski describes him “as a student of the game” who talked to teammates and quickly made adjustments after at-bats. Santander also became adept at reading pitchers. “He was very advanced for his age on understanding what pitchers had, what their out pitch was, what they were going to try to do to him as a left-handed hitter,” says Budzinksi. “He would tell me, ‘This guy’s going to try to get me out with a changeup. I’m going to take him deep.’ And he would do it. At 21 years old. I’d be thinking back to my career like, ‘Man, I would have never been able to do something like he just did right there.’”

Despite that standout performance in 2016 and all the talent and intelligence he’d shown, once the season ended and he became eligible for the Rule 5 draft, Cleveland didn’t add him to the 40-man roster. Santander had just undergone surgery on his right shoulder and the club bet that between the rehabilitation process, his injury history and relative inexperience, no team could carry him all season, even if it did claim him.

The Orioles, however, were immediately intrigued. With a team in the Carolina League, they’d watched Santander up-close throughout the season, believing him to be the best offensive player in the loop. “He showed a unique ability to hit for power from both sides of the plate, he was versatile in the outfield and he could hit — he didn’t have a lot of issues making contact,” says Duquette. Something else stuck out, too: “He got hit by a pitch a bunch [12 times] and he hung in there and hit 20 home runs at 21 years old. That distinguished him from other players available in the draft.”

Still, since Rule 5 picks must remain on the major-league roster for the entire season or be offered back to their original clubs, the odds were stacked against selecting a position player out of A-ball. Coming off a gutting loss to the Blue Jays in the American League wild-card game, the Orioles weren’t a likely candidate to sacrifice a roster spot to stash a prospect for a year; they were in a competitive window, not a rebuild. But Blue Jays ace Kevin Gausman, who was with Baltimore at the time, says then-manager Buck Showalter “loved Rule 5 guys” and picking them “was his thing. He loved that these guys are going to give everything they have, because if they don’t, they’re going back to the organization that was willing to give them up. He loved guys that had a chip on their shoulder.” During Showalter’s time with the Orioles, Rule 5 picks that stuck included infielder Ryan Flaherty, lefty T.J. McFarland, outfielder Joey Rickard, shortstop Richie Martin and, of course, Santander. 

Santander was ultimately the last of 18 players selected in that Rule 5, a process that had been completely unknown to him prior to a chance encounter with Colorado Rockies righty Antonio Senzatela at the Phoenix airport in late November. “He knew Cleveland didn’t put me on the 40-man roster and he said, ‘Wow, you had a good season why didn’t they?’” recalls Santander. “I explained to him why and then he was the first guy who told me about the Rule 5. But after that, I didn’t pay attention. I didn’t expect anybody to take me, honestly. I just played high-A and had shoulder surgery.”

That fateful Dec. 8 morning, though, his phone went off. First, his agent called to break the news and offer congratulations — “I said, ‘What? Explain it better, I still don’t know what that is,’” Santander remembers — and later, he heard from Kent Qualls, the Orioles’ director of minor-league operations, who arranged a flight to Baltimore. “I just said, ‘Okay, let me see how this works, what is it I have to do to be able to stay here,’” says Santander, “and that was a blessing.”

The selection didn’t surprise Budzinski, who remembers discussing the possibility with Rigo Beltran, his pitching coach in Lynchburg, toward the end of that 2016 season. “We were like, ‘if we don’t protect him’ — which, those are tough decisions to make, especially on an A-ball player — ‘there’s a chance he gets picked up,’” Budzinski says. “You could just see the tools and the person and the maturity, that somebody may take a shot. And obviously Baltimore did.”

Mike Elias took over as GM and Brandon Hyde, a finalist for the Blue Jays job that went to Charlie Montoyo that winter, became manager. Suddenly everything with the Orioles was under the microscope. As Elias combed through players in the organization, he remembers looking at Santander’s stats and thinking, “Who is this guy?” But holdovers in the organization vouched for Santander and “one of the cliches when you come into a new organization as a GM, or any position really, is to do as little as possible because you don’t know what you’re doing until you spend some time there.

“Had I acted on what I was seeing, which was his stats and the fact that he’s on the 40-man and the injuries, there really wasn’t a lot there to excite you,” Elias continues. “But the people that had seen him healthy said he was going to be worth taking a look at. Luckily for us, he hit the ground running in 2019, so it didn’t make it a difficult decision to plan around him.”

Hyde immediately took a liking to Santander, and a camp in which the outfielder went 11-for-33 with two homers and six doubles certainly helped. “I liked the way he used the whole field from both sides. I thought he was a really good athlete. I liked the way he played defence,” says Hyde. “So, we kept him for a long time that spring training.”

While he didn’t make the team, Santander impressed enough that the Orioles looked for an opportunity to bring him up. The first came as the extra man for a May 1 doubleheader at the Chicago White Sox, and Santander obliged with a home run. The second came June 7, when he was called back up for good.

“I give a lot of credit and thanks to Hyde and Mike,” says Santander. “In 2018, I struggled a lot and then I went to play winter ball [with the Tigres de Aragua in Venzuela]and I didn’t perform the right way at the beginning, but it helped me get my career back. I went to spring training. I did a really good job … In June, they gave me an opportunity again, they put me as an everyday player and the rest is history.”

Santander hit 20 homers with 20 doubles in 93 games that year and then went deep 11 more times in 37 contests during the pandemic-shortened 2020 season. Ankle and knee injuries limited him to 110 games in 2021, and that prompted him to change his strength and conditioning routine in the off-season, in search of better durability. “I had a really good work ethic, that’s really important, but I didn’t know how to work the right way,” he says. “I was just lifting like a bodybuilder.”

Working with Troy Jones, whom he still trains with, changed everything. They focused on activation, stability, flexibility and targeted lifting, all exercises designed “to keep the tissue quality really good to absorb everything we’re going to do [in-season] from a mobility standpoint,” Santander explains. “That’s why I’ve been able to stay healthy the last three years and play 150-plus games.”

The physical improvements allowed Santander to more fully put together his game. He played in 152 contests in 2022 and his 33 home runs and 89 RBIs helped drive the Orioles’ 31-win spike, to 83-79. The next year, when Baltimore surged to 101-61 and won the American League East, he added 28 homers and 95 RBIs in 153 games. Last year he peaked with 44 homers and 102 RBIs in 155 games as Baltimore earned a wild-card berth. Hyde, who grew close to Santander through regular long conversations, marvels at the way “he knew how pitchers were going to attack him and he would sit on certain pitches for at-bats.

“He does an amazing amount of research for himself and he prepares to face that starter as well as anybody I’ve seen,” the manager adds. Elias succinctly summed up Santander’s impact on the Orioles by calling him an “an enormous figure for us in restoring the franchise.”

It took until mid-January for the Blue Jays to emerge with the best combination of the three for Santander, who signed a creative contract that guarantees $92.5 million over five years, $61.75 million of which is deferred, according to an industry source. Included in the deal is a player opt-out after the third season that the team can negate by adding a club option for a sixth year, which pushes the total package to $110 million. The players’ union calculated the guarantee’s present value at $68.6 million, the deferment reducing the Blue Jays’ Competitive Balance Tax hit.

Santander says he didn’t sweat the relatively long wait to find his new home, explaining that as long as players understand the process, “it’s easy because there’s nothing I can do about it.”

“I felt like I did my job on the field. I did what I can do. Now, it is not in my hands,” he adds. “Just waiting for what we’re looking for. And we go from there.”

And go from there is what he’s done this spring, establishing relationships with new Blue Jays teammates who were once his rivals. Given that he hit more home runs against Toronto — 21 in 330 plate appearances — than any other club, he was somewhat of a nemesis in recent years. In the 2022-23 off-season, the Blue Jays added another such player, centrefielder Kevin Kiermaier, so they have some experience turning enemies into friends.

“You joke about it a little bit at first,” says manager John Schneider. “I’ve told [Santander] I used to hate when his first AB, he does that little dig in and kind of stares in the dugout, he’s looking at the clock. I wanted to punch him in the face every time he did that the last couple of years. And now I love when he does it, you know? … I told KK the same thing. I said I absolutely hated him for five years and now he’s one of the best people I’ve met in the game. Competition does that to you. I’m glad he’s on our side now.”

Santander is, too, a long way from the kid at the baseball academy trying to find his way, the young prospect in the Cleveland system who couldn’t stay on the field, the curious Rule 5 pick whom the Orioles managed to pilfer and transform into an all-star. All these years later he’s still in the kitchen, too, and the Blue Jays are ready to smell what he’s got cooking.