Toronto should’ve had it all.

The Toronto Blue Jays made a rather bold offseason gambit, targeting $700 million superstar Shohei Ohtani and nearly landing him. It would’ve been the biggest free-agent surprise in a minute. Ohtani was widely viewed as a future Dodger (correctly), but the Blue Jays made their pitch centered on star talent, a giant salary, and the unique multinational appeal of playing in Toronto.

Had it worked, we would probably be having very different conversations about the state of the Blue Jays in 2024. Ross Atkins might not be on the hot seat, and perhaps Toronto would be raking its way to the postseason. Unfortunately, Ohtani opted for the glitz and glamor of the West Coast, leaving Toronto high and dry.

Rather than repurposing that $700 million for other contract offers, the Blue Jays essentially sat on their hands. Matt Chapman was allowed to walk in favor of Justin Turner, a sizable downgrade. Toronto was briefly mentioned in connection to Juan Soto, but he ended up within the division, in the more sizable market. The Blue Jays were essentially victims of their own ambition, as Chris Bassitt shamelessly opined in a recent podcast appearance.

Chris Bassitt on what went wrong for the Blue Jays this year:

“We put I think $700 million into Shohei Ohtani’s basket and didn’t get him” pic.twitter.com/lA0Aksd03k

— Talkin’ Baseball (@TalkinBaseball_) August 19, 2024

Once Ohtani left Toronto holding the bag, they didn’t have a pivot. That is the excuse being made at least. Instead of wondering what could’ve been with Ohtani, however, Toronto fans surely wish the front office was more ambitious in using its resources to add star power of another variety. Ohtani isn’t the only needle-mover to change teams (or almost change teams) this year.

Here are a few trades Toronto should’ve made.

3. Jazz Chisholm Jr.

Jazz Chisholm Jr. has been the vibes savior of the 2024 New York Yankees. He arrived at the trade deadline with a mixed reputation. Chisholm was known to rub veterans the wrong way in Miami and he does not fit our cookie-cutter image of what a Yankees star normally is. The backwards hat, the colorful accessories, the boisterous personality. He’s way too fun to be a Yankee, and yet he is.

That could’ve been yours, Toronto! Few teams need to raise their spirits more than the Blue Jays. Chisholm has brought a sort of incandecent positivity to the Yankees, a team that was starting to feel awfully stale before the deadline. Aaron Judge and Juan Soto are the primary engines in Yankee land, but Chisholm backs up his personality with a tremendous, five-tool s𝓀𝒾𝓁𝓁 set.

He puts the barrel on the ball, he hits for power, and he’s a menace on the base paths. Chisholm is an incredible athlete in general, and at 26, he’s still putting the pieces together. There is considerable untapped upside. Moreover, Chisholm has been the ultimate team player, learning third base on the fly (and looking quite good) to pacify Gleyber Torres, who basically refused to change positions.

Chisholm was perfectly affordable relative to other big names moved this season. He’s 26 with multiple years of team control left and an All-Star on his resumé. He’s comfortable at several positions, both infield and outfield, and he’s the sort of live-wire playmaker the Blue Jays lack.

2. Luis Arraez

The Miami Marlins were ripe for the picking this season, but Toronto did not take advantage. Luis Arraez was dealt to the San Diego Padres early in the campaign, marking his third team in as many seasons. The appeal here is rather obvious. There just isn’t a better bat-to-ball threat in the MLB. Arraez can hit just about anything and he’s constantly on base as a result.

The slugging is limited, but Arraez has earned three straight All-Star appearances with his contact prowess. He can go fishing outside the zone with great success and Arraez is hardly ever swinging out of control. He’s in the MLB’s 100th percentile for both whiff rate (7.4) and strikeout rate (4.6), and he’s in the 99th percentile for expected batting average (.315). That implies that his .304 average is the result of minor bad luck.

With Bo Bichette going from the batting average king of the American League to a sub-replacement level shortstop, Arraez sure would’ve been a nice boon for the Blue Jays’ offense. He’s one of the most dependable leadoff bats in the MLB and he’s comfortable lining up all over the infield, giving Toronto some positional flexibility.

Still under team control through next season, Arraez wouldn’t cost an arm and a leg financially. Not yet, at the very least. If the Blue Jays weren’t itching to reroute that $700 million to pricey free agents, there were still worthwhile trade candidates with palatable salaries. The front office really doesn’t have an excuse.

1. Juan Soto

For a moment there, some thought the Blue Jays could land Shohei Ohtani and Juan Soto. What a pairing that would have been. Instead, the Blue Jays are sitting at the bottom of the AL East standings while Soto helps New York to the top. Toronto has zero top-100 prospects in its farm system, so there are logistical hurdles when trying to engineer a trade of this magnitude. Also, Soto is on an expiring contract, so there is serious one-and-done risk for the Yankees, not to mention the Blue Jays.

All the same, Toronto’s outlook would have been profoundly different had Soto landed north of the border. If the Blue Jays are willing to shell out $700 million for Shohei Ohtani, it shouldn’t be too unfathomable a leap to give Soto the $500-600 million he is about to demand. The rarity of 25-year-old superstars like Soto makes him a once in a generation trade (or free agent) candidate. There is technically still time for the Blue Jays to make a run at Soto this winter.

The Padres chickened out of the Soto bidding war (and could still circle back in free agency). The Yankees will not do the same, as several contenders are expected to line up around the block to pitch Soto on the glories on their respective teams and cities. Toronto would have been able to get a head start on its pitch, pairing Soto with Vladimir Guerrero Jr. in what could have easily been a competitive Blue Jays lineup. Toronto is a beautiful town by all accounts. One can’t help but think about what might have been.

Soto is the dream for just about every front office, but the Blue Jays were actually there, right in the mix. Not only did Toronto whiff on Soto, but they let him join a division rival who has since pummeled them all season long.

Missing out on Ohtani and Soto should’ve been a positive indicator for Blue Jays fan — a signal that the front office is finally ready to push all its chips in and compete for box office names. Instead, it basically meant the Blue Jays were done trying. They took the ‘go big or go home’ concept a little too literally, and opted not to pursue a Plan C or D once the big-ticket items were unavailable.

Oh, what could have been…