Santander says yes, but Sasaki no still stings

The Toronto Blue Jays finally turned the tables on the bridesmaid narrative with Anthony Santander, but the near-miss of Roki Sasaki still stings.

Two straight winters of trying and mostly failing to woo the sport’s biggest stars has left the entire fan base on edge, and Sasaki turning them down and running off with someone else in public fashion, in this case the very same Los Angeles Dodgers and last year’s fling, Shohei Ohtani, provided some more heartbreak.

A Japanese star publicly contemplating joining them, before a quick Instagram post kills those dreams in a flash. It’s deja vu.

Even though Jays fans never expected to be in position for the 23-year-old Sasaki a couple weeks ago, losing out on the Japanese ace at the last minute Friday evening was a crushing blow thanks to the magnitude of what that signing would’ve meant for the future health of the franchise.

As usual for these Blue Jays, it came with some drama, too, this time in the form of a money-eating trade with Cleveland to acquire international bonus pool space that was being used to lure Sasaki at the last minute.

When the music stopped, the Dodgers had yet another ace in Sasaki and the Jays have … Myles Straw and some extra money to sign a 16-year-old if they want.

Even with the final outcome doing more harm than good in terms of public perception, the Sasaki chase is one that the Jays should repeat over and over again if given the opportunity, and make no mistake, they actually did come fairly close to prying him away from the team that many felt he was destined for from the beginning, and ultimately was in the end.

Why all the fuss over Roki?

There’s been no secret to Sasaki’s dominance as he’s run up a 2.10 ERA across four NPB seasons in his early twenties.

A 100-mph heater and one of the nastiest splitters on the planet is a pretty good combo for success.

Throw in the fact that Sasaki is mature beyond his years on the mound and you have an arm worthy of the rare ace label.

That’s the expectation. Right away, too.

The Jays, like the rest of the baseball world, began scouting Sasaki way back in 2019 when the right-hander was just 17 years old.

Despite a blister that limited him, the Jays first saw Sasaki throw at the U-18 world juniors in Korea as a high schooler and no one needed a scouting background to see how special he could be.

The NPB draft would follow and MLB teams became aware that Sasaki may have a handshake agreement in place with the team that selected him, Chiba Lotte, to post him and let him leave sooner rather than later.

That eventually came to fruition late last year, as Sasaki decided he wanted to go the Ohtani route, which meant being restricted by amateur status and the international bonus pool, rather than wait like countryman Yoshi Yamamoto did last year.

It was a market-changing decision simply because of the fact it evened the financial playing field, leaving the door open for Sasaki to pull a surprise and choose a team off the beaten path, which is what Ohtani did when he joined the Angels.

For a brief moment, it looked like history would repeat itself.

But as he arrives in North America this spring, there are a handful of pink flags — they’re not even concerning enough to be red yet — that could come into play.

What was the pitch?

After an initial pitch early in the off-season, Sasaki’s camp agreed to visit Toronto in early January.

With the group of teams in the running for him thought to be finalized, Sasaki quietly arrived in Toronto on Jan. 9 and spent a couple days in the city, touring Rogers Centre and throwing for club officials.

With the club upping efforts in the Pacific Rim eight or nine years ago, this was the opportunity for it to pay off in a major way.

It doesn’t get any more franchise changing than luring a readymade ace who’s restricted to the league minimum for the first three seasons.

Pacific Rim area scout Hideaki Sato laid the groundwork, as did former major-league reliever Frank Herrmann, 40, a key component of getting Sasaki interested in Toronto when the time came, according to sources.

Herrmann, an economics major at Harvard who pitched in the Cleveland system for the current Mark Shapiro/Ross Atkins regime, was teammates with Sasaki on the Chiba Lotte Marines in 2021, shortly before the Jays hired him to work in a scouting and player development role.

Talking to players under contract Japan is a no-no, but how illegal is it to casually chat with a former teammate who is very connected in Japan from his time playing there?

The Jays weren’t sure how much of an in they had until a few weeks ago, but they laid as much groundwork as they could.

The final Straw?

On the day Sasaki was expected to make a decision, news broke early of the San Diego Padres being lopped off Sasaki’s list.

Given his relationship with Yu Darvish and all of the lovely things that come along with living in sunny San Diego, it was a bit of a surprise.

It was already creating some PTSD in Toronto seeing them up against the powerhouse Dodgers for a Japanese star, but hope was provided when the Jays surprisingly swung a late morning trade for $2 million in international bonus pool space.

Surely, they wouldn’t do this for nothing, right?

Behind the scenes, the Jays were simply making sure they emptied the clip and left no stone unturned in trying to get Sasaki to choose them and there was an honest belief that they weren’t in the driver’s seat.

The price of trading for more international money to throw at Sasaki at the last minute was taking on outfielder Myles Straw and $11 million of the $14.75 million he’s owed through the 2026 season.

This is all about optics and the fact they came up short.

Straw, who’s expected to fill a speed and defence bench role if he’s on the roster, has been a useful player in the past with a 3.0 fWAR season on his resume from 2021, but they clearly did the penny-pinching Guardians a huge favour.

The Jays also had offers to send out a good prospect in exchange for bonus pool money — which the Dodgers eventually did in a trade with the Philadelphia Phillies — but they decided to use some financial clout to take on Straw instead.

According to sources, the money added in the failed attempt to swing for the fences with Sasaki will not limit their spending in any way whatsoever as they attempt to pick up the pieces and pivot, likely to the free-agent bats still sitting on the market in this late stage of the roster building process.

The proof will be in the pudding when it comes to that, but there seems to be ample money to spend and quality talent available to spend it on.

The Jays finally heard a yes on Monday, inking Santander to a lucrative five-year, $92.5-million deal with a club option for a sixth season and an opt-out clause after three years.

Santander fits and helps satisfy an extreme need for instant offence, but perhaps more importantly it shows that high-end free-agents will eventually say yes to Toronto.

Just not all of them.

With a career high of 129.1 innings on his resume currently, durability will be a question until he proves he can handle a bigger workload and stay off the injured list.

Make no mistake, that was part of the Jays’ pitch.

The pristine health of Kevin Gausman, Jose Berrios, Chris Bassitt and others over the last handful of years isn’t something to overlook in an age of pitcher injuries.

The Jays had the fewest IL days for starting pitchers in all of baseball in 2024.

And one of the teams that’s had UCLs popping left and right and man games piling up for starting pitchers on the injured list is the team Sasaki decided to join.

Last year, Sasaki was even two full ticks down, with his fastball sitting in the 96-97 mph range for much of the year.

Still high-octane, but still less stuff than he had in 2023.

There’s also the fact he’s always pitched with an extra day of rest in Japan, but those with knowledge of the Jays’ plan for Sasaki had them putting him on a traditional every-fifth-day schedule and trying to push him back and give him that extra day as much as possible.

That would mean having extra optionable starting pitching depth on hand for spot starts, which the Jays don’t really have built up at this point.