This season has not turned out well for the Toronto Blue Jays.

They’re nine games under .500. They’re in last place in the AL East, 15 games out of first. They are 10 games out of the last AL Wild Card spot. This is a team that made the playoffs last year and the year before, with three straight seasons of 89-plus wins, and now they’re facing roughly 1% odds of reaching the postseason, per FanGraphs. The 2024 season has been a mess. And, considering how expensive this team is, how little playoff success it has had and how many players will soon be hitting free agency, it might just be the end of an era in Toronto.

That’s a shame: This Blue Jays team had so much promise and fan support. But knowing when it’s time to move on is a valuable skill. Which is why it has been surprising that the Blue Jays have been so hesitant to do the one thing that would close the door on this era and create a bridge to the next one: trade four-time All-Star first baseman Vladimir Guerrero Jr.

Sources told MLB.com’s Mark Feinsand earlier this month that the Blue Jays won’t be looking to trade anyone who is under contract beyond this year, ostensibly because they plan on contending in 2025. That eliminates Vlad Jr., who is due to hit free agency after next season. But this is the sort of mistake that the Blue Jays can’t afford to make. They may have one real opportunity – this real opportunity – to stock the next contending Jays team by trading Vlad Jr. while he has a maximum value, rather than standing pat in a quixotic attempt to contend.

The Blue Jays don’t look like they want to trade Vlad Jr. But they should. Here are five reasons why.

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1) The 2025 Blue Jays may not contend, either

One of the reasons the Blue Jays have said they’re only trading guys who aren’t under contract beyond this season is that there are so many of them on expiring deals, including Justin Turner, Yimi García, Yusei Kikuchi, Danny Jansen and Trevor Richards. There are some valuable players there, but that speaks to the larger point: Toronto likely will be losing most or all those players next year. The Blue Jays are a last-place team with them. Without them, it’s hard to see this club improving.

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Considering how frustrating this year has been, do you see the Blue Jays really spending a ton of money on free agents this coming winter? They tried to do that last offseason, fell short in their pursuit of Shohei Ohtani and others, and ended up with this. The youngest regular in this lineup is Vlad Jr.: This isn’t a lineup waiting to bust out. (Also, the rotation is so old.) I don’t see how the Jays can get all that much better next year than they were this year. So why keep Vlad Jr.?

2) The AL East is on the way up

We’ll see about the Rays, who are in their own little state of limbo right now. (But they always seem to figure something out.) The rest of the AL East, however, looks like it’s going to be stocked with powerhouses for a while. The Orioles are great right now, and they also have a whole Triple-A Norfolk roster loaded with future Camden Yards regulars. They sure look like they’re going to be aggressive both at this Trade Deadline and in the offseason. The Yankees certainly aren’t going anywhere and may end up giving Juan Soto all the money.

And – and this is the perilous part for the Jays – the Red Sox sure look like they’ve turned a corner, with a load of exciting players in their 20s, led by Rafael Devers, Connor Wong, Ceddanne Rafaela and All-Star Game MVP Jarren Duran. Wait until they start really spending money. It seems like the Red Sox have passed the Blue Jays not just in the short term, but the long term as well. There was a time when the Sox, Yankees and Orioles were all down. That time has passed. The Jays didn’t take advantage, and there is no longer an advantage to be had.

3) A Vlad Jr. extension would have happened by now

I find it difficult to blame the Jays for this one. After the 2021 season, it looked like Guerrero was going to be a top-tier superstar. After the 2022 season, it looked less so. After the 2023 season, he looked … pretty good, with flashes of brilliance, but little consistency. It has been the same thing this year. You keep expecting Vlad Jr. to become the MVP runner-up he was in 2021 – he is only 25 after all – but every year it doesn’t happen, you wonder if maybe the smart thing to do is to let somebody else pay him for a future production level that we haven’t actually seen in three years.

Toronto could have committed to Guerrero but didn’t. So why hang on to him now, only to wave goodbye to him after next year for nothing more than a compensatory Draft pick? Teams sign their young stars to massive long-term contracts all the time, but the Jays and Vlad Jr. never figured it out. And now it’s too late. Why would he agree to stay here now when he could have years ago? He won’t. So get what you can while the getting is good.

4) There could be a hot market

First base/DH types aren’t usually top-shelf items, with teams tending to save their best prospects for pitching, or for five-tool guys who can play premium positions. But, in a stroke of good fortune, there are three teams that desperately want to win right now with a primary need for a Guerrero-type player.

There are the Mariners, who just placed Ty France on outright waivers. There are the Yankees, who have enjoyed rookie Ben Rice’s emergence in place of the injured Anthony Rizzo but could hardly consider him irreplaceable. (Guerrero recently walked back previous comments he made about never playing for the Yankees.) And there are the Twins, who have solid veteran Carlos Santana at first but could very much use another big bat. While it’s hard to say exactly what sort of package those teams might part with to bring in Vlad Jr. for multiple playoff chases, each certainly has enticing prospects to offer.

There’s no bigger-ticket item on the market than Vlad Jr. And there are teams that need him.

5) This is the best chance to build the next great Jays team

All is not lost for the Jays. They have a terrific fanbase, a motivated ownership group and a smart front office. They’re not going to disappear for a decade. But they do need an injection of talent. And there’s no better way to get that than by trading Guerrero. As much as some of those pending free agents could help a contender, they are, after all, pending free agents: Toronto will only get so much for them. (Shortstop Bo Bichette, who might have been another prime trade chip, is hurt and enduring by far his least productive season.)

So Vlad Jr. is the only truly valuable piece the Blue Jays have. Fortunately, he’s really valuable, particularly at this specific Deadline. While Vlad Jr. is a player this fanbase and this front office have invested many hopes and dreams in, for years now, it’s highly likely that he won’t be a Blue Jay by November 2025.

The Jays gave it a run with this roster. It didn’t quite work out. It’s time to focus on the next one. It’s time to trade Vlad Jr.