Blue Jays’ pursuit of star Orioles outfielder won’t be enough to delay the inevitable

Do the Toronto Blue Jays want to follow in the footsteps of the Chicago White Sox? Even though Toronto actually won five of the six contests against the historically inferior team on Chicago's South Side in 2024, the extent of the good news ends there. Toronto needs to learn the lessons of Chicago's recent collapse and apply them to their pursuit of top free agent bats this winter.

In all seriousness, the White Sox have been a bad organization for a really long time. The club has been around for over a century, with just three championships to show for their labor (one in the modern era). Starting in 2014, they kicked off a stretch in which they finished no higher than fourth place for five straight years. They made the playoffs in the expanded pandemic season and swiftly bowed out. With manager Rick Renteria on the way out, the Sox needed to recognize that a full-fledged rebuild was exactly what the doctor ordered. Instead, an ill-fated marriage with Tony La Russa largely resulted in two wasteful seasons, followed by the current turmoil. The Sox missed the boat, and they should be a cautionary tale for all teams refusing to embrace a roster rebuild.

Anthony Santander has recently emerged as one of the top names connected to the Toronto Blue Jays, as they do everything they can to get players to accept their money. He would, in theory, provide plenty of power to a lineup in desperate need of it. Santander scalded 44 home runs last season and posted the highest OPS+ of his career in a full season. In playing 155 games last season, the Orioles slugger and former Rule 5 pick demonstrated sturdiness after a strong stretch in which he batted .247 with 79 homers and 234 RBI in 415 games between the 2021 and 2023 seasons.

In a vacuum, Santander is a fine addition for a team that wants to contend immediately. Except baseball clubs don't operate in vacuums. Toronto resides in a particularly troublesome spot with expensive contracts on their books and a mostly destitute farm system. It's not like Toronto has all kinds of cheap labor coming through the doorway. The George Springer contract isn't going anywhere! Hello, Andres Giménez and his big money.

Blue Jays must pick total rebuild over Anthony Santander signing

A team caught in this conundrum can ill afford to tie themselves to an unwieldy contract that they may come to regret someday. Truthfully, Santander does have some red flags. He certainly hits for plenty of power, but there are questions about his batting average and defensive fit. It has the feelings of a player who performed well in a free agent year with a somewhat murky future. This may not be the smartest move for a team that needs a lot to go right in a hyper-competitive division.

We saw this happen in Chicago when they got into bed with Andrew Benintendi on a record-breaking contract for a team that needed to rebuild. Was the Lance Lynn extension really worth it for a team that wasn't winning anytime soon?

The Blue Jays are in a position where the best prescription could be avoiding ill-fated maneuvers. Don't do stupid stuff! Of course, Jays fans understand the extent of the problems facing this team. The easiest way to begin addressing them is to ensure there are as few obstacles as possible standing in their way.

The Blue Jays are trying to do everything at once. That course of action is destined to fail when you accomplish exactly nothing. While the Jays desperately need a power bat, they also need a laundry list of other gifts that can't realistically be acquired in the current time frame. The Jays only need to look around the sport and find plenty of teams who made these mistakes to serve as close-proximity cautionary tales.