Mark Shapiro’s Blue Jays tenure has been marked by limited baseball ambition — and fans longing for Alex Anthopoulos

Think back to the moment Shapiro arrived. That was in the summer of 2015, in the midst of the thrilling late-season rally that saw the Blue Jays morph from a group of 50-51 underachievers to champions of the American League East. It was an electric run that ended a 22-year playoff drought — the longest in the four major North American sports at the time — and on the day Shapiro was hired, the Jays won for the 24th time in 29 games. The day before, veteran catcher Russell Martin said: “If this isn’t the feel of a championship team, I don’t know what is.”

And it happened thanks in no small part to Anthopoulos’s deadline trades to acquire David Price, Troy Tulowitzki and Ben Revere. When the Sporting News polled major-league executives, the Blue Jays GM was their landslide choice as baseball’s executive of the year.

As it happened, the award was officially announced moments before Anthopoulos did a media conference call discussing his departure from Toronto. Shapiro had been brought in to supplant retiring team president Paul Beeston — Jays chair Ed Rogers infamously and unwittingly called Beeston’s best friend in baseball, White Sox owner Jerry Reinsdorf, to ask about replacing Beeston with White Sox exec Kenny Williams — and Shapiro was given a mandate to modernize the club’s business operation, along with authority over baseball decisions. It didn’t matter that the consensus in baseball at the time was that Cleveland had shuffled Shapiro upstairs to their presidency after his successful early tenure as GM petered out. The deal was done.

Behind closed doors, Shapiro made it clear immediately that Anthopoulos was not a part of Toronto’s future; after the Blue Jays lost to Kansas City in six games in the American League Championship Series, Anthopoulos submitted his resignation to the Rogers Communications board. This caused a brief panic, and ownership offered Anthopoulos an unusual arrangement: full autonomy over baseball operations, reporting directly to the Rogers board. They essentially offered to undermine their newly hired president of baseball operations.

Anthopoulos, however, is someone who believes in institutional clarity, and holds deep principles. The Beeston protege declined.

“I love the Blue Jays,” Anthopoulos said on his way out. “By no means is this an easy decision, but it’s one that I needed to make.”

Anthopoulos has done fine beyond Canada’s borders. After a stint in the Los Angeles Dodgers front office, he was hired to run the Atlanta Braves in 2017. The Braves won the National League East in each of his first six seasons with the club, and won the World Series in 2021.

So you’ll excuse fans of the Jays if they’d like to recapture the moment of magic Anthopoulos helped conjure north of the border. When Anthopoulos departed, the Jays weren’t just World Series contenders. They were the most exciting team in baseball, complete with the most potent offence in the major leagues. And in Anthopoulos they had a Montreal-born executive who didn’t just have a deep knowledge of the hard numbers that govern a game driven by analytics, but also a growing understanding that the game, ultimately, comes down to the people who play it — that clubhouse chemistry has to be a factor, too. And as for the ultimate success of a team, well, a lot of it comes down to the size of vision of the people who run it. As Beeston used to repeatedly remind Anthopoulos: “Think small and you’ll be small.” Which helps explain Anthopoulos’s penchant for the big swing.

And then there’s Toronto. Since the 2016 post-season run to the ALCS against Cleveland with the remains of the Anthopoulos team — minus Price, Mark Buehrle, and more — the Jays have played six playoff games, and lost them all. They were among the World Series favourites before the 2022 season but under-delivered, blowing an 8-1 lead en route to being swept by the Mariners in the wild-card series. There were those who still believed in Toronto’s potential in 2023, before a wild-card sweep by the Twins. The peak of the organization’s analytics-driven process saw them pull a red-hot José Berríos in the fourth inning of last fall’s Game 2 loss, after which GM Ross Atkins passed the buck of what was clearly an organizational decision to manager John Schneider.

“Those meetings are John Schneider’s meetings,” Atkins said of the strategy sessions that produced Toronto’s playoff playbook.

More than anything, it suggested the Jays might do just as well if run by robots. Certainly robots couldn’t be as tone deaf to the market’s growing skepticism. With popular faith waning, this past off-season the Jays followed up a much-hyped and ultimately failed pursuit of Shohei Ohtani by making relatively minor tweaks to their power-starved offence, while insisting “internal improvement” would be their route to a better year.

“We have a team in place that we’re exceptionally excited about,” Atkins said in the lead-up to this season.

As salesmen go, let’s just say Atkins would go hungry in the used-car business.

His boss isn’t exactly more convincing. Shapiro, too, paid lip service to improving the on-field product after last season.

“We need to get better,” he said at a season-ending news conference. “I’m not satisfied with where we are, Ross isn’t satisfied with where we are.”

Alas, the off-season saw the Jays essentially remain in precisely the same place. With the Jays predictably among the game’s most feeble offences yet again, the front office’s belief in an imminent turnaround sounds more and more like a con job on a fan base that’s becoming wise to the grift. After 2021, in fact — a year the Jays missed the playoffs in a 91-win season thanks to a lack of quality depth, a flammable bullpen and the disruptions of COVID — Toronto leaned further into an AL Central-style team based on pitching and defence. It’s been smaller and smaller ball, in baseball’s big-boy division.

In some ways, Shapiro has achieved a worthy goal. He has convinced Jays ownership — the same ownership that has been getting outspent by its rivals for decades, to the point that Anthopoulos made the 2015 trades with existing budget money rather than asking for ownership permission — to spend money. Sure, Shapiro’s biggest bets have been on contractors; a $400-million renovation to Rogers Centre and a $102-million remake of the club’s Dunedin player-development complex have both come with impressive results.

But on the field, Toronto is projected to rank eighth in payroll, according to FanGraphs. Getting a team president who can speak the corporate language of Rogers, and who can manage up effectively, can be beneficial to the ball club.

The problem is that Shapiro’s Jays haven’t been particularly deft at spending the money, on a team capped by its own limited ambition. Anthopoulos was often tantalized by a player’s ceiling. He bet big on José Bautista despite a limited track record, took swings on guys such as Colby Rasmus and Brandon Morrow. His 2012 trade with Florida was more about dependability — Buehrle, José Reyes, and a lottery ticket gone bust in Josh Johnson — but Anthopoulos loved hunting upside.

Shapiro and Atkins appear more interested in finding athletes with dependable floors. You can make a list of known commodities that includes Steve Pearce, Jaime García, Tanner Roark, Brandon Belt, Justin Turner, Isiah Kiner-Falefa, Kevin Kiermaier. Yusei Kikuchi, Yariel Rodríguez, and Lourdes Gurriel Jr. could be considered a sort of exception. But while Anthopoulos tended toward swinging for the fences, Shapiro and Atkins appear more content with safe-choice singles.

The Jays also don’t have many cheap, player-development-fuelled, pre-arbitration contracts, not with a farm system that ranks among the worst in baseball at the moment. Shapiro’s first meeting with Anthopoulos involved lengthy complaints about the young players the organization had traded to bolster the team at the deadline, so this might qualify as irony.

There’s a bigger irony, though. If Rogers ownership was responsible for squandering one of the game’s great baseball executives — much less a homegrown one who loved being close to family in Montreal and was passionate about baseball in Canada — then you have to admit they got one thing right. When the board offered Anthopoulos control over baseball operations, with Shapiro relegated to the business side, they inadvertently may have proposed the ideal arrangement.

Based on skill sets alone, Shapiro and Anthopoulos could have been a great team: a business guy to pry open the owner’s pocket, a baseball guy to ensure the money got maximized. Without the visionary, ambitious, sometimes swashbuckling Anthopoulos at the wheel, the idea that the Jays could be one of the biggest teams in baseball has been replaced by a safer, more corporate vision. They are just risk averse enough to fall short, without strong enough organizational fundamentals to make up for the lack of truly big swings.

As for those investments, if they’re the gold-star bullet points on the president’s resumé, they come with consequences. After all, is a team that just foisted on its best customers a dramatic ticket-price increase in any position to sell at the trade deadline and begin a rebuild? It seems unlikely.

Still, a strong case can be made that a rebuild is in order. If Bo Bichette and Vlad Guerrero Jr. aren’t true linchpins — and with a year each remaining on their current deals, the jury is still out on their worthiness as long-term core plays — there is little reason to believe this club possesses the building blocks of the “sustainable” contender Shapiro once vowed to build. And there’s even less of a reason to believe there are young saviours in the minors. Again, Baseball America ranked Toronto’s farm system 24th before this season, with just two Jays prospects ranked among the top 100. It doesn’t help that the division-rival Baltimore Orioles, already a major-league powerhouse, are the consensus pick as the richest in emerging talent. It doesn’t help that the New York Yankees, after looking vulnerable in recent seasons, have re-established themselves as a behemoth.

Playing in the AL East has always been a hard slog. If you lack the elite draft-and-develop factory of a team such as the Tampa Bay Rays, it requires real ambition and big swings, and a considerable annual cash outlay. Shapiro has achieved the latter without the former. All these years later, beyond a prettier ballpark and a gleaming spring-training complex, the return on capital certainly has yet to be paid in post-season success.

It’s almost too easy to construct an alternative history: the continuation of the Jays under Anthopoulos, who was preparing ambitious trades for Joey Votto, maybe Ben Zobrist, along with re-signing Price, as part of a plan to keep the good times rolling. Instead, Shapiro and Atkins let that 2015 team fizzle: Price went to Boston, J.A. Happ was repatriated, and the deadline was a series of nibbles on relievers with unsightly ERAs (some worked out better than others).

This front office hasn’t had a more accomplished team since. That door slid shut, and we are nearing a verdict on a near-decade of a front office which certainly seems like the right fit for Rogers. They just may be the wrong guys for everybody else.