The Toronto Blue Jays can’t win the World Series at the trade deadline, however, if the correct moves are made, they could position themselves for a deep playoff run in October. So, what moves need to happen?

Well, there are some obvious flaws with Toronto’s roster. Offensively, they probably need to acquire a proven left-handed hitter to make their lineup a little more balanced. But that’s not the main weakness of this group. Everyone knows they can score boatloads of runs even with a right-handed-heavy offence.

Pitching is where this team must improve the most, especially in the bullpen. There’s only one problem with that, though, so too does almost every other contending team. Quality relievers are always in high demand during this time of the year. And with the expanded playoff format, there won’t be as many sellers at this year’s trade deadline and in future ones, too.

Having said that, there are a handful of franchises who’ve already been virtually eliminated from post-season contention, particularly those near the bottom of the standings in the National League. As for which ones stand out the most in terms of pitching depth, the Chicago Cubs could serve as an intriguing trade partner for the Blue Jays.

With a disappointing 32-48 record, placing them fourth in the NL Central, the Cubs remain focused on the future and they could further strengthen their prospect system by dealing key members of their bullpen. At the backend, they feature one of the most well-known pitchers in the game, David Robertson.

Robertson is pitching in his 14th big-league season and with his fifth different franchise over the last five campaigns. That number will almost certainly grow to six before this season ends. And perhaps he could add a Blue Jays uniform to his collection, Toronto would surely benefit from acquiring his services.

At 37, the 5’11” hurler isn’t the same dominating pitcher he was during his prime years with the New York Yankees, although he remains an impact player in late-game situations. The right-hander has converted 11 saves across 32.1 innings while acting as Chicago’s primary closer. That’s tied for 12th-most in the majors.

In total, Robertson has performed to a 1.95 ERA, a 2.92 xERA and a 3.27 FIP in 29 appearances with the Cubs. He’s also recorded plenty of strikeouts, earning him a 33.3 per cent rate – his highest since 2017 (37.1 per cent).

Generating swings and misses haven’t been an issue for Robertson, as his 33.9 per cent whiff rate ranks in the 92nd percentile of the majors, according to BaseballSavant. His strikeout rate ranks in the 93rd percentile.

The 2011 American League All-Star has also done an excellent job at inducing ground balls, resulting in a career-best 52.2 per cent clip. He’s been effective at limiting hard contact, as well, as his hard-hit rate against (34.3 per cent) ranks in the 75th percentile, with his average exit velocity against (87.8 m.p.h.) placing in the 69th percentile.

While Robertson doesn’t blow hitters away with velocity, which is unusual for a closer in today’s era, the veteran reliever makes up for it with spin. Robertson’s low-90s cutter – his primary pitch – features an average spin rate of 2,691 RPMs, placing it in the 100th percentile. The righty’s mid-80s curveball – his secondary weapon – also carries a high spin rate (2,641 RPMs), ranking it in the 72nd percentile.

As a high-strikeout reliever, Robertson would be an ideal target for the Blue Jays at the trade deadline, although he will be a free agent in the off-season. Still, adding him to a bullpen that’s headlined by Jordan Romano could make for a potent one-two punch.

Even if Toronto were to acquire Robertson, however, that probably wouldn’t be enough to solidify their bullpen ahead of the stretch run. But Chicago possesses more than just one quality reliever. Their pitching staff includes another talented righty, Scott Effross.

Who’s Effross and why haven’t you heard of him before? Those are two great questions. The biggest reason why he’s unfamiliar to most baseball fans is that this is just his first full season in the majors. But don’t be mistaken, the 28-year-old is well-equipped to excel at this level.

In 37 appearances this season, the 6’2″ right-hander has posted a 3.09 ERA and a 2.11 xERA through 35.0 innings. His 0.9 fWAR rating is tied for seventh-highest in the majors among qualified relievers.

Most notably, Effross generates a ton of strikeouts as he owns a 30.6 per cent rate. The former 15th-round selection also forces opposing hitters to extend the strike zone, earning him a 34.0 per cent chase rate. He also doesn’t allow many free passes to first base, resulting in a 6.3 per cent walk rate.

Another encouraging trait is that he barely surrenders any hard contact. Currently, his barrel (4.4 per cent) and hard-hit rates against (35.2 per cent) rank in the 90th and 69th percentiles, respectively.

Though, the most intriguing aspect of Effross’ craft is his delivery. It’s one Blue Jays fans have become very familiar with every time Adam Cimber takes the mound. Thanks to his deceptiveness, the Cubs’ reliever is capable of fooling batters with his slider-sinker combination, which usually break in the opposite directions.

Could you imagine pairing Effross and Cimber together? It’d almost be unfair to have a pair of side-throwing relievers in the same bullpen.

What makes Effross even more appealing is that he’d come with several additional seasons of team control. He won’t be arbitration-eligible until after 2024 and can’t hit free agency until after ’27. That means the earliest he could hit free agency would be following his age-33 season.

There’s a chance the Cubs might not be willing to trade him. Or at least, they might need to be persuaded to part ways with him, likely increasing his acquisition cost.

If that’s the case and Effross proves too expensive, the Blue Jays would likely be forced to shift their focus elsewhere, although that could potentially lead them to Keegan Thompson. And that might not be the worst possible outcome.

Thompson possesses a very similar skill set to Ross Stripling. He’s extremely versatile and can serve as both a starter and a reliever. With Hyun Jin Ryu injured for the rest of 2022 and potentially all of 2023, Toronto desperately misses having Stripling in the bullpen. But that’s where Thompson could become a valuable piece.

As a reliever, the 27-year-old carries a 1.38 ERA and a 2.96 FIP over 26.0 innings this season. He’s also produced a 25.3 per cent strikeout rate, an 8.1 per cent walk rate and opponents are hitting just .184 against him. His ground ball rate also sits at a remarkable 58.1 per cent clip.

Granted, Thompson’s results in the starting rotation aren’t nearly as flattering as he boasts a 4.57 ERA, however, he’s registered at least seven punch-outs in three of his last four starts. He’s also allowed two runs or fewer in three of those four outings. So it seems he’s beginning to find his groove as a starter.

Similar to Stripling, Thompson features a full complement of weapons against both righties and lefties. His six-pitch arsenal includes a mid-90s four-seamer, low-90s cutter, low-80s curveball, mid-80s change-up, mid-90s sinker and a newly-developed mid-80s slider.

The former third-round selection largely only throws his slider to right-handers, but because of its 10.7 inches of average horizontal break, it’s able to induce plenty of laughable swings and misses.

At this stage of his career, it appears Thompson is only scratching the surface of his full potential. If he were granted the opportunity to work alongside pitching coach Pete Walker and Toronto’s talented coaching staff, the versatile hurler could potentially emerge into a major difference-maker.

Like Effross, Thompson isn’t scheduled to hit free agency until after the 2027 season. He also isn’t arbitration-eligible for another two seasons, making him first-time eligible in ’25. But that likely means he’d be fairly expensive to acquire, too.

Obviously, the Blue Jays will need to determine how much they’re willing to pay to improve their bullpen by the trade deadline. Are their top-end prospects untouchable? What about their promising young arms at the lower levels? Could any of them be moved to help the big-league club?

If the front office answers yes to any of these questions, it’ll almost certainly increase their chances of landing any two or all three of Robertson, Effross and Thompson. Any combination of that trio would immediately transform the outlook of Toronto’s bullpen.

Even if a deal can’t be struck with Chicago, though, management will need to add some much-needed swing and miss to this current group.