When will the Rays trade Tyler Glasnow?

That’s right, I said WHEN not IF

The Rays trading their ace Tyler Glasnow, who has one year remaining on his contract, is being treated as a foregone conclusion by reporters both in Tampa Bay and nationally.

So when can we expect such a deal to go down? There are three important factors to consider:

1. The Winter Meetings

The 2023 Baseball Winter Meetings will take place Dec. 4-7th, in Nashville, Tennessee. These meetings are often the fertile ground in which trades and and free agent signings take root.

When the Rays have traded an ace in the past, it has usually come in December in the weeks following the Winter Meetings, which is often followed by a flurry of activity that makes the path to trading a key role player like a No. 1 or No. 2 starter clear.

2. The aces still in the deck

Speaking of clear starters, teams are unlikely to trade for a player like Glasnow until the best free agents are either off the board or their intentions made clear on where they intend to sign. Here it is helpful that Aaron Nola has already decided to return to Philly, but there are two names that could clog the pitching pipeline.

The first player is 25-year old phenom Yoshinobu Yamamoto, who has won the NPB’s Cy Young equivalent three years running, and may be in line for a free agent contract nearing $200 million. Teams wanting to trade for Glasnow will likely want to know if Yamamoto is considering their club.

Likewise, there is Blake Snell, coming off his own Cy Young season and entering the free agent market at age-31. Snell is likely to get a guarantee in the $25 million AAV range, so teams missing out on Snell will likely see 30-year old Glasnow as a strong alternative atop the pitching market.

The other alternatives are a tier down from the ace level, such as World Series winner Jordan Montgomery, 34-year old Sonny Gray, or recent contract opt-out Eduardo Rodriguez. Those players may cost a little less than Glasnow’s contract on a single season basis, but of course would be looking for long term deals. If you’d rather pay for quality and go back to market next year, Glasnow is a better alternative to these three.

3. Shohei Ohtani

Ohtani is an interesting thought experiment in this context. Due to an elbow injury, Ohtani is not expected to pitch until 2025, and will instead be considered as a designated hitter for the first year of the deal.

In other words, instead of holding up the pitching market for 2024, he’ll actually be holding back the DH market (which could have implications for the Rays if they’re looking to deal Harold Ramirez or Yandy Diaz).

Nevertheless, Ohtani is sure to have an impact on two important elements of the market: owners’ pocketbooks, and the actions of other players.

Ohtani is likely to sign the richest free agent deal in MLB history this off-season, with expectations around $450 million if not more. If money is no question for his signing team, maybe acquiring Glasnow helps make up for Ohtani not pitching in 2024, but other than the Mets who could that be? Instead, I’d expect Ohtani’s singing team to be not as interested in taking Glasnow’s salary on the books, because...

Where Ohtani lands is sure to lead to a lot of interest for the other free agents, most notably Yamamoto who reportedly (and reasonably) prefers to sign with a club that has other Japanese players.

So when will this all go down?

The good news with the above is that we can expect most of these transaction to go down in and around the 2023 Winter Meetings, which again lines a Glasnow deal up with the week or two following as medicals are exchanged and cleared. For context, in a similar environment Blake Snell was traded Dec. 28, 2020.

Alternatively, if an acquiring team already knows they are not the intended destination for any of the key players listed, we could see a deal come even sooner. For example, James Shields was traded to the Royals (who were not big free agent players) on Dec. 9, 2012.

Now, could it be possible we get a trade even sooner? Sure, there’s always a possibility that a team wants to settle their roster needs before heading into the Winter Meetings, in the same way you might want to order some goods online before heading to the store, but that only escalated our timeline.

Either way, if Tyler Glasnow is on the move, expect to know before the new year.

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Read More: Should the Rays trade Tyler Glasnow or Randy Arozarena?