New San Diego Padres shortstop Xander Bogaerts James A. Pittman-USA TODAY Sports

Xander Bogaerts’ first visit to free agency resulted in an 11-year, $280M deal with the Padres that greatly exceeded projections, even for a player who was expected to land one of the offseason’s biggest contracts.  Agent Scott Boras discussed some of the twists and turns of Bogaerts’ free agent trip with USA Today’s Bob Nightengale, and Boras identified that Bogaerts was San Diego’s second choice, once Trea Turner rejected a reported $342M offer from the Padres.

Once Turner turned down the Padres’ offer to sign with the Phillies, “we kind of knew the Padres’ guy was Bogaerts,” Boras said.  “They wanted that personality, that leadership in that locker room.”  Left unspoken by Boras was the fact that the Padres were clearly itching to land a big target of some kind, even to the point of considering a $400M bid for Aaron Judge.  With Judge and Turner off the board, the Padres may have been more willing to go above and beyond to sign Bogaerts, and ensure that their offseason endeavors would include at least one superstar name.

The Red Sox reportedly made a last-ditch effort to sign Bogaerts in the hours preceding his deal with San Diego, though Sox chief baseball officer Chaim Bloom later downplayed the chances that a reunion between Bogaerts and the Red Sox was becoming a possibility.  There were mixed signals from Boston’s ownership and front office all season long about the franchise’s willingness to retain Bogaerts, and from Boras’ perspective, the Red Sox weren’t ever a major bidder.

It was just really clear to us there was a separation where Boston was going to go for Bogaerts, compared to where the market was,” Boras said.  “They probably made a decision they were going to sign [Rafael] Devers, and were going to pay only one of them.  So we knew at the forefront that Bogey would be somewhere besides Boston.”

Sure enough, the Red Sox indeed ended up extending Devers, while Bogaerts landed in San Diego.  As for other teams in the hunt, such teams as the Phillies, Diamondbacks, Orioles, Mariners, Dodgers, and Giants were all linked to Bogaerts at various points in the offseason, even if some of these pursuits were perhaps more cursory than others.  Boras implied that three teams in particular (beyond the Padres) separated themselves from the pack, saying that “Minnesota, the Cubs, the Blue Jays, they were really after” Bogaerts’ services.

The Cubs and Twins were already known to be Bogaerts’ suitors, and as both clubs were monitoring the high-end shortstop market and eventually came away with two of the winter’s top options at the position — Chicago signed Dansby Swanson, while Minnesota (eventually) reunited with Carlos Correa.  The Twins’ interest in Bogaerts was framed as a backup plan if Correa signed elsewhere, though Bogaerts ended up signing with the Padres before Correa agreed to his initial deal with the Giants.  As for the Cubs, MLB.com’s Mark Feinsand wrote that the team gave some consideration to the idea of signing both Bogaerts and Swanson, with Bogaerts playing third base in that blockbuster scenario.

It makes for some fascinating “what-if” material, since neither the Twins or the Cubs were previously considered top candidates to sign Bogaerts.  However, the Blue Jays’ involvement is perhaps the most interesting, as Toronto hadn’t previously been linked to Bogaerts or any of the top shortstops whatsoever.  While the aggressive Jays are known to be a team that routinely checks in on most free agents as a matter of due diligence, Toronto’s focus was known to be on the club’s greater needs in the outfield and in the rotation.  Such names as Justin Verlander, Brandon Nimmo, and Kodai Senga were among the many players linked to the Blue Jays, and Toronto has thus far signed Chris Bassitt, Kevin Kiermaier, and Brandon Belt, while Daulton Varsho and Erik Swanson were respectively acquired in major trades with the Diamondbacks and Mariners that saw Gabriel Moreno, Lourdes Gurriel Jr., and Teoscar Hernandez change uniforms.

These moves have sent the Jays’ payroll to franchise-record heights, and set the team up to exceed the luxury tax threshold for the first time.  So in that sense, making a splash to sign Bogaerts wouldn’t have been out of line with the Blue Jays’ spending habits, even if obviously landing Bogaerts would have entirely changed the scope of Toronto’s offseason.

First and foremost, the Blue Jays already have a star shortstop in Bo Bichette, who is only entering his age-25 season and already amassed two top-12 finishes in AL MVP voting, an All-Star nod, and 9.6 fWAR in 2021-22.  (For comparison, Bogaerts had 10.4 fWAR in 2021-22.)  Bichette’s success at the plate, however, was tempered by a rather drastic defensive decline in 2022, as public metrics placed Bichette among the league’s worst defensive players.  Ironically, Bogaerts’ glovework had long been a source of controversy, but he quelled some doubts over his viability as a shortstop by delivering the best defensive season of his career in 2022.

Had the Jays signed Bogaerts, they could’ve installed him at shortstop and moved Bichette to second base, and then used the current collection of second-base options (i.e. Santiago Espinal, Cavan Biggio, Whit Merrifield) either purely as depth options or as trade chips.  Since Matt Chapman is a free agent after the 2023 season, the Blue Jays might’ve considered moving Bogaerts to third base at that point and returning Bichette to shortstop, if Chapman wasn’t retained.  Or, if signing Bogaerts would’ve taken up much or all of Toronto’s payroll space, the Blue Jays might have been considered trading Bichette in order to address other needs.  If the Jays hadn’t had the money to sign a Bassitt-level starter, for instance, Bichette could have been shopped to land a front-of-the-rotation arm.

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