Why Jordan Montgomery may wait until the season starts to sign

As this incredibly slow offseason has dragged on, much attention has been paid to the free agents who remained unsigned into February and March. There were many players in this group but a lot of attention was paid to the so-called “Boras Four,” which consisted of Cody Bellinger, Matt Chapman, Blake Snell and Jordan Montgomery.

The attention was understandable as they were the highest-profile of the guys languishing in the open market. At the start of the offseason, just about every outlet that predicts such things pegged those four to get lengthy nine-figure pacts. But as the winter dragged on towards the spring, many teams claimed to be at their spending limits, either due to uncertainty around TV revenue or competitive balance tax implications.

In recent weeks, three of those four players have pivoted to short-term deals with fairly high average annual values and opt-outs. In each case, the player can pocket a sizeable salary and then return to the open market in the future if they feel the chance of netting a mega pact will be better.

Bellinger returned to the Cubs on a three-year, $80M deal, in which he can opt out after each of the first two seasons. Chapman got three years and $54M from the Giants, also with opt-outs after the first two years. Snell will join Chapman in San Francisco after signing a two-year, $62M deal that will let him opt out after this coming season.

Montgomery’s situation is slightly different than those three in one way. The other three received and rejected a qualifying offer at the end of the 2023 season, meaning they were tied to signing penalties this winter. The penalties vary depending on whether the team is a revenue-sharing recipient or a competitive balance taxpayer, but a club has to forfeit one draft pick at minimum, sometimes two picks and also international bonus pool space. Players can only receive one QO in their career, so they won’t have to worry about those penalties in future trips to free agency.

Montgomery is in the opposite situation. He has yet to receive a QO and would not currently require a signing team to forfeit anything. Players are only eligible for a QO if they spend the entirety of the just-completed season with the same club. Since the lefty was traded from the Cardinals to the Rangers in the middle of the 2023 campaign, he wasn’t eligible to get a QO coming into this offseason.

That makes it somewhat complicated for him to consider the short-term, opt-out-laden pacts that the other Boras guys settled for. While they all just shed their QOs and will be free from them going forward, Montgomery is currently free but could be in position to be saddled with a QO down the road. As recently as March 8, he was reportedly holding out hope of landing a lengthy seven-year deal. The fact that he remains unsigned suggests that he never got it and it’s hard to see a team making that kind of plunge at this late stage of the offseason.

Since Opening Day is now just over a week away, with most teams starting their seasons on March 28, perhaps it would be wise for him to look for the best short-term deal he can find but wait until after Opening Day to actually sign it. The collective bargaining agreement states that the QO applies to players who become free agents “after having been continuously under reserve (without interruption) to the same Club (either at the Major or Minor League level) since Opening Day of the recently completed championship season” and who have not previously received a QO from any club.

Perhaps waiting would make Montgomery more amenable to a short-term pact with opt-outs, as he wouldn’t have to worry about a qualifying offer, at least after 2024. Hypothetically, if he signed a two-year pact like Snell and decided not to trigger his opt-out, he could be given a QO after the 2025 campaign unless he was traded midseason again.

It’s also possible there would be an on-field logic to the move. Montgomery’s 188 2/3 innings in the regular season were a personal high and then he added another 31 frames in the postseason as he helped the Rangers win the World Series. Players sometimes talk about a “World Series hangover” where they experience a bit of extra fatigue in a season following a deep playoff run since it shortens the offseason rest period. Delaying his spring ramp-up could perhaps give him some extra rest and avoid any of those hangover effects.

The flip side of this strategy is that a club could perhaps factor a future QO into the price of their contract offer. Starting with whatever dollar value they place on Montgomery as a pitcher, they might be willing to add a few million to that if they feel there’s a high chance of him opting out and then netting them a future draft pick. By intentionally waiting until the season starts, Montgomery would presumably be taking that bump out of the picture.

That’s all speculation, to be clear, but it’s known that teams place internal values on draft picks. Mets owner Steve Cohen tweeted a few years ago that picks are worth up to five times their slot value to teams. Last year, picks 68-70 of the draft went to the Cubs, Giants and Braves. Those clubs had given QOs to Willson Contreras, Carlos Rodónand Dansby Swanson, respectively, and received compensation picks when they signed elsewhere. Per MLB.com, those picks each had a slot value a bit over $1M.

Waiting to sign in-season due to concerns around the QO isn’t unprecedented, but this would be different than past instances. Some players who rejected QOs in the past waited until after the draft was completed to sign new contracts, therefore washing away the draft pick penalties. Dallas Keuchel, Craig Kimbrel and Kendrys Morales are some of the players who signed in June, after the draft. Stephen Drew was on a path to a similar fate in 2014 before the Red Sox, his previous club, realized their chances of getting any QO compensation were dwindling and just re-signed him.

Montgomery’s situation is different in that he only needs to wait one day into the season in order to make him ineligible to receive a QO after 2024. Since the QO can negatively impact a free agent’s earning power and the season will have started for all 30 clubs by next Thursday, perhaps he could sit tight a little bit longer.