Finally a win in the Blue Jays' winter of discontent

Perhaps it was an elaborate prank.

For the second time this offseason, and the third time in two years, the Toronto Blue Jays managed to get close to landing a generational free agent, the kind of player who would transform the franchise, only to whiff in the end.

The Jays' front office has become the MLB equivalent of Charlie Brown kicking the football. On its last attempt, the failed pursuit of Roki Sasaki, Toronto introduced a humiliating new wrinkle: acquiring international bonus-pool money from the Cleveland Guardians as the seeming final step in the process of getting the Japanese star, only for him to indicate hours later that he intended to sign with the Los Angeles Dodgers.

The cost of acquiring that ultimately unnecessary bonus-pool money: the two years and almost $14 million owed to outfielder Myles Straw, who can do everything except hit, which he cannot do at all. The notoriously cheap Guardians were so convinced he wasn't a major-league hitter that they paid him $5 million last season to stay in Triple-A.

It's such an objectively bad bit of business that it defies belief. Did general manager Ross Atkins and president Mark Shapiro think Sasaki was coming to Toronto, and the move with the Guardians was just the cost of completing a deal for a possible superstar? Were they unsure of his plans but made the Straw trade to show Sasaki how serious they were about landing him? There was either a huge gamble, a terrible miscommunication, or some combination of the two, and now a front office that's been defined by prudence for nine years is left with a terrible contract it acquired for no reason.

And then, finally, a reprieve. Toronto found a big target who was willing to accept its money: former Baltimore Orioles outfielder Anthony Santander, whose 44 home runs last season represent a desperately needed addition to a Jays lineup that was 13th in the American League in home runs last year.

Atkins and Shapiro probably have to add another power bat - Pete Alonso and Alex Bergman remain available - to salvage a winter that has been heavy on swings and misses. But this is at least a start, and it presents some evidence that the Jays haven't become radioactive.

Even if they do add another power bat - which would almost certainly require making the kind of risky deal they usually avoid - Jays management still faces the thorny question of Vladimir Guerrero Jr.'s looming free agency. While there's plenty of time left to make a deal before his self-imposed spring training deadline, the Jays have let the franchise's most important player get perilously close to his walk year. (They're in a similar spot with Bo Bichette, but his situation is at least slightly more complicated due to a 2024 season beset by slumps and injuries.)

The notion that the Blue Jays could lose Guerrero for nothing is almost inconceivable (much like accidentally trading for an overpaid, no-hit outfielder for no good reason). The economics of baseball are simple enough: If you have a homegrown superstar, he'll expect a huge contract by the time he hits free agency, even if that contract carries into the years when his abilities will likely decline. That's just the way the sport works; guys are underpaid in their early years of team control and overpaid once they finally get leverage.

Many franchises avoid this problem by trading their best players while they're still under team control, extracting a prospect haul, and letting some other team worry about the potential mega-contract. (We see you, Athletics.) Or they pay the stars early, buying out some free-agency years but giving them a long-term deal that overpays in the short term. (Hello, Braves.)

The worst-case scenario is doing neither of those things. If the Blue Jays weren't willing to pay Guerrero an eye-watering amount that would carry a considerable degree of long-term risk, then they should have traded him years ago when he was one of the hottest prospects in baseball. Either you accept the reality of a monster contract for a franchise cornerstone, or you discourage fans from getting too attached to the team's young stars. The Jays have been acting like the New York Yankees for some time now; it's too late to start behaving like the Tampa Bay Rays.

Shapiro and Atkins catch a lot of flak, and not all of it is deserved. They did build playoff teams, even if those teams couldn't win an actual playoff game.

Adding Santander at least means that Toronto's front office hasn't spent the entire offseason chasing ghosts. The Jays have a lot left to do, but bringing in a big bat is a lot more than they've managed since November.

Scott Stinson is a contributing writer for theScore.