The closer one looks at this year’s crop of free-agent pitchers the trickier it gets for the Blue Jays’ off-season plans.

Toronto desperately needs to upgrade its rotation. That much is obvious, and the Jays will be the first to admit it’s their top priority. General manager Ross Atkins isn’t hiding from it either and last week went as far to tell the Star he expects to “add significantly” to the starting staff.

That’s the type of news every Jays fan should want to hear, but how the club intends to accomplish that goal, and who the targets will be, remains a mystery. There are a lot of familiar names that keep surfacing in the rumour mill and yet it’s hard to shake the feeling Toronto’s top goal is much easier to state out loud than it is to put into action.

Gerrit Cole and Stephen Strasburg aren’t realistic targets, no matter how well they might complement Toronto’s young core. Ownership group Rogers Communications has the money to sign either one, but this organization hasn’t seriously considered that level of a free agent since the early 1990s and there’s no reason to believe that stance will change any time soon.

Instead, the Jays have been expected to be shop in the mid-tier market and that’s where things get complicated. There are plenty of options available. It’s the quality of those options that continues to be a bone of contention. Lots of arms and not a lot of guarantees any of them will help turn this organization around.

Right-hander Zack Wheeler is considered the headliner for this second grouping of free-agent starters. The 29-year-old is coming off a year in which he went 11-8 with a 3.96 ERA and 195 strikeouts over 1951/3 innings. Wheeler struggled throughout the first half, but put himself in position for a big payday this winter by allowing just 24 earned runs over his final 761/3 innings for the Mets.

Earlier this season, the speculation was that Wheeler would be in line for a five-year deal around $75 million (all dollars U.S.). By the end of 2019, MLB Trade Rumors was projecting a five-year deal in the vicinity of $100 million. The latest reports, including from Dan Hayes of The Athletic, suggest the asking price might be even $20 million higher.

Whatever team signs Wheeler will be taking a massive risk. A front office will bank on the notion that Wheeler’s best work is yet to come and that his checkered health is a thing of the past. Wheeler made 60 starts over the last two seasons, but prior to that he had a litany of injuries including a stress reaction in his right arm, biceps tendinitis and Tommy John surgery.

There are a lot of red flags and just as many teams that won’t care. No matter what the issues are, organizations will be lining up to bet on the arm. It pays to be a hard thrower, especially as a starter, and Wheeler has one of the most powerful arsenals in the game with a fastball that averages 96.7 m.p.h. with an above-average spin rate. The Phillies, Padres, White Sox, Twins and Angels are among those known to have interest. Money talks, but based on the names of those teams alone it’s easy to see why the Jays have yet to be named as one of the front-runners.

If there comes a point when Wheeler’s price tag is ruled out, things get a lot more complicated for the Jays because — outside of possibly Dallas Keuchel — the remaining options leave a lot to be desired. Madison Bumgarner, Hyun-Jin Ryu and Cole Hamels don’t seem very likely for a variety of reasons, including age and their expected desires to play for a contender.

After that group, the quality in talent drops significantly. Kyle Gibson is off the board after joining the Rangers on a three-year deal worth $30 million earlier this week, which leaves the likes of Michael Pineda, Tanner Roark, Rick Porcello and Andrew Cashner as the more notable names available.

Anyone from that group would fit on Toronto’s roster, but nobody with a straight face could describe them as significant additions. They are stopgap solutions that might help the Jays win a few more games in the short term, but will do little to advance this team’s chances at competing in 2022 and beyond.

A positive thinker will believe Atkins finds himself in an enviable position. He has money to spend, a strong minor-league system to work from and an exciting young core of position players. A more negative view would suggest Atkins’ back is up against the wall because he is searching for the exact same thing so many other teams are. The fact he needs two, maybe even three pitchers makes it that much more daunting.

MLB’s off-season is typically slow to develop, so it would be foolish to make any sweeping judgments about Toronto’s off-season before the winter meetings have even arrived. The Jays are just getting started, but if the top free agents have been ruled out, it’s natural to have genuine concern about what happens if guys such as Wheeler and Keuchel are deemed off limits as well.

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How successful Atkins is in navigating these landmines will determine how quickly the Jays get back into contention. It would be risky to commit more than $100 million to someone like Wheeler but it might be even riskier not to, if it means another version of Jaime Garcia or Clayton Richard stepping onto the mound.

Patience is a virtue and Atkins has plenty of time to make waves, but if someone like Wade Miley ends up being the biggest addition to this starting rotation, this off-season will go down as a major failure. The ball is in Toronto’s court and this is one off-season where they almost have no choice but to make something happen.

Significant adds have been promised, significant adds will have to be delivered. Somehow, some way.

Gregor Chisholm is a Toronto-based baseball columnist for the Star. Follow him on Twitter: @GregorChisholm or reach him via email: gchisholm@thestar.ca

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