Jeremiah Masoli has put in his time in the Canadian Football League, going from practice roster player to backup quarterback to starter, albeit in a shared role most of the past two seasons with Dane Evans in Hamilton.

He is about to get rewarded for all that patience.

Masoli is 33, has been healthy through most of his career and helped take his team to back-to-back Grey Cup games. By all accounts, he’s an outstanding teammate who has never flinched in the face of competition for his job.

That resume makes him the most desirable commodity on the CFL free agent market, where teams are operating in the legal tampering window before the signing period opens on Feb. 8.

When the Ticats signed Evans in early January, it was widely assumed that Masoli would simply head east to Ottawa to reunite with new Redblacks general manager Shawn Burke, who was part of Hamilton’s senior management team until December.

Ottawa has been a disaster at quarterback the past two seasons, auditioning a series of players who were either too old, too young, or simply not good enough.

They don’t want to go into the 2022 season with a question mark hanging over the game’s most important position. That’s why the Redblacks are all in on pursuing Masoli.

The Edmonton Elks might also be chasing Masoli, which seems a little puzzling at first. But it makes sense once you lift the lid on what’s transpired with their quarterback situation over the past few months.

Former general manager Brock Sunderland acquired Nick Arbuckle in a trade from Toronto in October, then signed him to an extension at $340,000 for the 2022 season. The Elks restructured that deal in early January and included a $100,000 signing bonus which, on the surface, looked like an endorsement from Chris Jones, the team’s new head coach and general manager.

Why then would the Elks be interested in Masoli, given payment they just made to Arbuckle? Well, it turns out that both contracts Arbuckle signed – the extension announced last fall and the one restructured in January – were negotiated by Sunderland before he left, the second one being reserved until it could be determined that the league was going to allow signing bonuses this off-season.

Essentially, the Elks honoured a handshake deal made by their former general manager when they gave Arbuckle $100,000 at the start of January.

But their pursuit of Masoli suggests they aren’t committed to Arbuckle, and Jones is believed to have kicked the tires on Michael Reilly before he announced his retirement.

So, what does Ottawa do if the Elks land Masoli? Well, here’s where it gets interesting.

Besides Masoli, there are four quarterbacks on the market with at least some starting experience, and each comes with some context.

The first is Trevor Harris,  who was Ottawa’s starting quarterback in both 2017 and 2018 – years in which he threw for almost 9,800 yards and 22 touchdowns.

It was Harris’ exit via free agency after the 2018 season that started the downward spiral for the franchise. Could the prodigal son really come home?

Or what about Nick Arbuckle, who would presumably become available the minute Edmonton signs Masoli? Under former general manager Marcel Desjardins, Ottawa traded for Arbuckle’s rights and signed him after the 2019 season.

But after the 2020 season was cancelled, the Redblacks pivoted to Matt Nichols, setting Arbuckle free. Could Ottawa hit the reset button with Arbuckle two years later?

Montreal’s Matthew Shiltz, another pending free agent, played well in relief last season but doesn’t have the resume to be considered a proven starter.

Which brings us to Chris Streveler, the former Winnipeg backup and physical freak who has spent most of the past two seasons backing-up Kyler Murray with the NFL’s Arizona Cardinals.

Streveler was released late in the regular season and signed to Baltimore’s practice roster a short time later. A free agent again, he’s waiting on the NFL but apparently isn’t prepared to sit out the season if no offers come his way.

Ottawa head coach Paul LaPolice was Streveler’s offensive coordinator in Winnipeg, so there is familiarity with his strengths and weaknesses.

The issue is whether Streveler throws the ball well enough to be a full-time starting quarterback, something that’s been debated since he entered the league as a rookie with Winnipeg in 2018.

Given the question marks around their options beyond Masoli, it’s easy to see why Ottawa is focused on landing him.

And why Masoli’s timing couldn’t be better.