Interesting Wrinkle in Jordan Montgomery’s Free Agency, Cubs May Be Over CBT Level Already

We’re just 10 days away from the start of the regular season and several big-name free agents are still searching for teams. Even signing immediately would leave too little time for starting pitchers to get ramped up by Opening Day, but Jordan Montgomery may have added incentive to wait longer. As noted by Greg Zumach of North Side Bound, a wrinkle in the qualifying offer system could delay the lefty’s inevitable decision.

Montgomery seemed to have a leg up on some of his colleagues because he hadn’t declined a qualifying offer and thus was not saddled with the associated penalties. But if we look at the deals being offered at this point, it seems likely that Montgomery may be looking at a contract with at least one early opt-out. If he exercises that option, however, he would very likely head back to the market next year with scarlet letters on his chest.

Unless, as Zumach pointed out, he waits until after the start of the season to sign. According to the CBA, players must be continuously under reserve to the same team since Opening Day of the previous season in order to be eligible for a QO.

With that in mind, it’s entirely possible Montgomery has already reached a tentative agreement with a team and is simply waiting to sign until the end of the month. Or perhaps Scott Boras is fielding multiple offers and using this point as leverage for a bigger guarantee. Either way, it’s a great find by Zumach and something worth watching.

As for whether and how this could impact the Cubs, well, that is another interesting topic. I don’t tend to believe they’re hot after Montgomery and Sahadev Sharma reported recently that they “don’t appear to be a real contender” for his services, particularly given their payroll situation. Unless Montgomery ends up taking a deal for under $20 million in average annual value, which is hard to imagine if he’s forced to accept the kind of pillow contract he has reportedly refused to do so far, inking him could push Chicago into the second penalty tier.

Please understand that I’m not saying they shouldn’t push payroll to that point, as I’m all in favor of them spending as much as possible. Rather, it’s a matter of keeping with the idea that they probably view that $257 million level as a far more firm cap than $237 million. And if we can trust the estimates at Roster Resource, the Cubs are already a skosh past that first level at $237,055,715 as of this publication. There’s still plenty of noise in there, not to mention a lot of time to move one way or the other based on transactions during the season, but we can be sure they’re at least very close to penalty range.

As such, is Montgomery a guy they view as being worth pushing up against or into the second tier of luxury taxes? I don’t think so, especially when they’ve already got three southpaws in the rotation. It would be a very different story if Montgomery is willing to bet on himself with a short-term deal for less than $20 million AAV, but that seems more than a little unlikely for reasons laid out above. But hey, it’s been a really weird free agency period.

We know the Cubs like to be opportunistic with additions, so, even as long as the odds might look in some cases, I won’t count them out on Montgomery or anyone else until those players sign elsewhere.

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