There’s a saying in baseball: “Flags Fly Forever”.

I don’t like the saying. As a Toronto Raptors fan, I cherish the run they had in 2019 when they won the Larry O’Brien Championship. Yes, those memories will live with me until I’m gone, but damnit, I wish they won another ring or two, especially in 2020.
Want to know what I dislike a lot more than that saying? Squandering seven years of Vladimir Guerrero Jr. and Bo Bichette without a single playoff win. We’re entering that seventh and final season of team control, with the two players set to become free agents after the 2025 season.
The closest the Blue Jays came to being serious contenders under the Mark Shapiro and Ross Atkins regime was in 2021, when ironically, they didn’t make the playoffs thanks to some blown games early in the season. After losing in two consecutive Wild Card Series, the Blue Jays missed the postseason in 2024 thanks to the worst bullpen in the league, as well as cold bats.
There are plenty of holes in the roster heading into the 2025 season and simply put, the Blue Jays need to show some urgency in filling those holes. This isn’t the first time the Blue Jays have been put in a position such as this. 
<h2>The lack of urgency showed in 2014</h2>
Former Blue Jays general manager Alex Anthopoulos is still a loved figure in Blue Jays land, especially after leading the Atlanta Braves to a World Series in 2021. However, his tenure before the 2015 season is often not discussed. The Canadian-born general manager took over the Blue Jays at the end of the 2009 season, missing the postseason in his first five seasons.
See, Anthopoulos has always been a general manager that goes for it. That goes either way, as there were quite a few trades in his past that weren’t great, to say the least, namely the Roy Halladay deal and the R.A. Dickey deal. We’ll get to when going for it works well later.
The one time Anthopoulos didn’t go for it was at the 2014 trade deadline. On July 30, 2014, the Toronto Blue Jays had a 59-50 record and held the final Wild Card spot while being 2.5 games behind the division-leading Baltimore Orioles.
Instead of looking to add to their roster, Anthopoulos stood pat, something that <a href="https://www.sportsnet.ca/baseball/mlb/bautista-disappointed-by-jays-quiet-deadline/">Blue Jays icon José Bautista was </a><a href="https://www.sportsnet.ca/baseball/mlb/bautista-disappointed-by-jays-quiet-deadline/">not </a><a href="https://www.sportsnet.ca/baseball/mlb/bautista-disappointed-by-jays-quiet-deadline/">happy about</a>, and for good reason. In the final two months of the season, the Blue Jays finished with a 24-29 record, 13 games back of the Orioles, and third in the American League East.
The question is, did Anthopoulos learn his lesson?
<h2>The urgency showed in the 2015 season</h2>
After the disappointing 2014 season, the Blue Jays hadn’t made the postseason for 21 consecutive seasons, the longest drought in North American sports at the time. Interestingly, the last time they made the postseason was in 1993 when they won back-to-back World Series, which was the final time a Canadian team in the Big Four North American sports leagues won a championship until the Toronto Raptors did so in 2019.
Anyway, Blue Jays general manager Anthopoulos had swung for the fences as we briefly touched on in the last section. Before the 2013 season, he made two blockbuster trades, moving prospects Travis d’Arnaud and Noah Syndergaard (who looked like an ace early in his career) for reigning National League Cy Young winner, R.A. Dickey. Moreover, he acquired Mark Buehrle, José Reyes, and others from the Miami Marlins. These two trades didn’t help in the short term, but all three players weren’t important to the 2015 team in various ways.
Despite the lack of short-term success with those trades, it didn’t dissuade Anthopoulos from making more big moves. In late November 2014, Anthopoulos traded Brett Lawrie, Sean Nolin, Kendall Graveman, and Franklin Barreto to the Oakland Athletics for Josh Donaldson. 
<blockquote class="twitter-tweet" data-width="550" data-dnt="true">
The <a href="https://twitter.com/BlueJays?ref_src=twsrc%5Etfw">@BlueJays</a> have acquired JOSH DONALDSON from the Oakland Athletics for BRETT LAWRIE, SEAN NOLIN, KENDALL GRAVEMAN and FRANKLIN BARRETO.
&mdash; Toronto Blue Jays (@BlueJays) <a href="https://twitter.com/BlueJays/status/538536684879896577?ref_src=twsrc%5Etfw">November 29, 2014</a></blockquote>
<script async src="https://platform.twitter.com/widgets.js" charset="utf-8"></script>
Moreover, the team acquired Marco Estrada, Devon Travis, and Michael Saunders through trade, useful players for what was to come. A few weeks after the Donaldson trade, Anthopoulos and the Jays signed Canadian catcher Russell Martin.
Despite all these moves, the Jays started the season with a 23-30 record over their first 23-30 games. Even after rattling off a 14-2 record over their next 16 games, they ended July 28, 2015, with a 50-51 record, eight games back of the division lead and three games back of Wild Card position.
On July 29, the Blue Jays traded José Reyes and prospects to the Colorado Rockies for Troy Tulowitzki. The following day, the Jays traded some more prospects and young players to the Detroit Tigers for ace David Price.
<blockquote class="twitter-tweet" data-width="550" data-dnt="true">
.<a href="https://twitter.com/BlueJays?ref_src=twsrc%5Etfw">@BlueJays</a> acquire Troy Tulowitzki and LaTroy Hawkins from COL in exchange for Jose Reyes, Jeff Hoffman, Miguel Castro &amp; Jesus Tinoco <a href="https://twitter.com/hashtag/Tulo?src=hash&amp;ref_src=twsrc%5Etfw">#Tulo</a>
&mdash; Toronto Blue Jays (@BlueJays) <a href="https://twitter.com/BlueJays/status/626045452421611520?ref_src=twsrc%5Etfw">July 28, 2015</a></blockquote>
<script async src="https://platform.twitter.com/widgets.js" charset="utf-8"></script>
You know the rest of the story, the Blue Jays came back from the dead winning 14 of their next 15 games (with the loss on August 1 being my all-time favourite game) and eventually won the division. They completed the reverse sweep over the Texas Rangers and should’ve beaten the Kansas City Royals.
However, if Anthopoulos never decided to go for it, especially at the trade deadline the aura of the 2015 Blue Jays would’ve never been born. The 2016 Blue Jays, led by Mark Shapiro and Ross Atkins, also made the American League Championship Series, before starting the rebuild outright in 2018.
Safe to say, Anthopoulos learned his lesson from the 2014 trade deadline.
<h2>The current regime needs to show urgency</h2>
I don’t think it’s a stretch to say that the 2024 season for Mark Shapiro and Ross Atkins was what the 2014 season was for Alex Anthopoulos. Expectations were high, but the Jays didn’t come close to living up to them.
This isn’t a pro-Anthopoulos/anti-Atkins stance; I think both tenures had their ups and downs. There’s a lot to like about what the current regime has done, such as the trades they’ve made, the fact they’ve spent money in free agency, and the renovation of Rogers Centre. If Anthopoulos’ game plan is the definition of “Flags Fly Forever”, Shapiro and Atkins’ game plan is the definition of “aiming for long-term success with holding prospects”.
With that being said, they’ve never really swung big at the trade deadline (their biggest move being acquiring José Berríos at the 2021 deadline) and while they’ve spent, they’ve never landed a superstar free agent (the closest signing being George Springer).
Entering the final season of Vladimir Guerrero Jr. and Bo Bichette’s deals, the Blue Jays have to be ultra-aggressive in acquiring players if they wish to contend. They have to be the highest bidders for Juan Soto, and if that falls through, they have to use the “special budget” they have on him for other needs.
There needs to be a pivot in place if Soto signs elsewhere, whether that being signing two big bats and an ace starting pitcher, or a big trade to acquire a superstar, it needs to happen. If there’s even a chance to make the postseason at the trade deadline, Atkins can ill afford to stand pat, they need to go big and acquire players that fill holes.
A few years ago, holding onto prospects for long-term success made more sense, but we’re about to enter the 2025 season and Vladimir Guerrero Jr. and Bo Bichette have yet to win a postseason game before they’re set to enter free agency at the end of the season. It’s time for the Blue Jays to be in “Flags Fly Forever” mode.
<hr />
As always, you can follow me on Bluesky @ryleydelaney.bsky.social.

There’s a saying in baseball: “Flags Fly Forever”.



I don’t like the saying. As a Toronto Raptors fan, I cherish the run they had in 2019 when they won the Larry O’Brien Championship. Yes, those memories will live with me until I’m gone, but damnit, I wish they won another ring or two, especially in 2020.

Want to know what I dislike a lot more than that saying? Squandering seven years of Vladimir Guerrero Jr. and Bo Bichette without a single playoff win. We’re entering that seventh and final season of team control, with the two players set to become free agents after the 2025 season.

The closest the Blue Jays came to being serious contenders under the Mark Shapiro and Ross Atkins regime was in 2021, when ironically, they didn’t make the playoffs thanks to some blown games early in the season. After losing in two consecutive Wild Card Series, the Blue Jays missed the postseason in 2024 thanks to the worst bullpen in the league, as well as cold bats.

There are plenty of holes in the roster heading into the 2025 season and simply put, the Blue Jays need to show some urgency in filling those holes. This isn’t the first time the Blue Jays have been put in a position such as this. 
<h2>The lack of urgency showed in 2014</h2>
Former Blue Jays general manager Alex Anthopoulos is still a loved figure in Blue Jays land, especially after leading the Atlanta Braves to a World Series in 2021. However, his tenure before the 2015 season is often not discussed. The Canadian-born general manager took over the Blue Jays at the end of the 2009 season, missing the postseason in his first five seasons.

See, Anthopoulos has always been a general manager that goes for it. That goes either way, as there were quite a few trades in his past that weren’t great, to say the least, namely the Roy Halladay deal and the R.A. Dickey deal. We’ll get to when going for it works well later.

The one time Anthopoulos didn’t go for it was at the 2014 trade deadline. On July 30, 2014, the Toronto Blue Jays had a 59-50 record and held the final Wild Card spot while being 2.5 games behind the division-leading Baltimore Orioles.

Instead of looking to add to their roster, Anthopoulos stood pat, something that <a href="https://www.sportsnet.ca/baseball/mlb/bautista-disappointed-by-jays-quiet-deadline/">Blue Jays icon José Bautista was </a><a href="https://www.sportsnet.ca/baseball/mlb/bautista-disappointed-by-jays-quiet-deadline/">not </a><a href="https://www.sportsnet.ca/baseball/mlb/bautista-disappointed-by-jays-quiet-deadline/">happy about</a>, and for good reason. In the final two months of the season, the Blue Jays finished with a 24-29 record, 13 games back of the Orioles, and third in the American League East.

The question is, did Anthopoulos learn his lesson?
<h2>The urgency showed in the 2015 season</h2>
After the disappointing 2014 season, the Blue Jays hadn’t made the postseason for 21 consecutive seasons, the longest drought in North American sports at the time. Interestingly, the last time they made the postseason was in 1993 when they won back-to-back World Series, which was the final time a Canadian team in the Big Four North American sports leagues won a championship until the Toronto Raptors did so in 2019.

Anyway, Blue Jays general manager Anthopoulos had swung for the fences as we briefly touched on in the last section. Before the 2013 season, he made two blockbuster trades, moving prospects Travis d’Arnaud and Noah Syndergaard (who looked like an ace early in his career) for reigning National League Cy Young winner, R.A. Dickey. Moreover, he acquired Mark Buehrle, José Reyes, and others from the Miami Marlins. These two trades didn’t help in the short term, but all three players weren’t important to the 2015 team in various ways.

Despite the lack of short-term success with those trades, it didn’t dissuade Anthopoulos from making more big moves. In late November 2014, Anthopoulos traded Brett Lawrie, Sean Nolin, Kendall Graveman, and Franklin Barreto to the Oakland Athletics for Josh Donaldson. 

https://twitter.com/BlueJays/status/538536684879896577

Moreover, the team acquired Marco Estrada, Devon Travis, and Michael Saunders through trade, useful players for what was to come. A few weeks after the Donaldson trade, Anthopoulos and the Jays signed Canadian catcher Russell Martin.

Despite all these moves, the Jays started the season with a 23-30 record over their first 23-30 games. Even after rattling off a 14-2 record over their next 16 games, they ended July 28, 2015, with a 50-51 record, eight games back of the division lead and three games back of Wild Card position.

On July 29, the Blue Jays traded José Reyes and prospects to the Colorado Rockies for Troy Tulowitzki. The following day, the Jays traded some more prospects and young players to the Detroit Tigers for ace David Price.

https://twitter.com/BlueJays/status/626045452421611520

You know the rest of the story, the Blue Jays came back from the dead winning 14 of their next 15 games (with the loss on August 1 being my all-time favourite game) and eventually won the division. They completed the reverse sweep over the Texas Rangers and should’ve beaten the Kansas City Royals.

However, if Anthopoulos never decided to go for it, especially at the trade deadline the aura of the 2015 Blue Jays would’ve never been born. The 2016 Blue Jays, led by Mark Shapiro and Ross Atkins, also made the American League Championship Series, before starting the rebuild outright in 2018.

Safe to say, Anthopoulos learned his lesson from the 2014 trade deadline.
<h2>The current regime needs to show urgency</h2>
I don’t think it’s a stretch to say that the 2024 season for Mark Shapiro and Ross Atkins was what the 2014 season was for Alex Anthopoulos. Expectations were high, but the Jays didn’t come close to living up to them.

This isn’t a pro-Anthopoulos/anti-Atkins stance; I think both tenures had their ups and downs. There’s a lot to like about what the current regime has done, such as the trades they’ve made, the fact they’ve spent money in free agency, and the renovation of Rogers Centre. If Anthopoulos’ game plan is the definition of “Flags Fly Forever”, Shapiro and Atkins’ game plan is the definition of “aiming for long-term success with holding prospects”.

With that being said, they’ve never really swung big at the trade deadline (their biggest move being acquiring José Berríos at the 2021 deadline) and while they’ve spent, they’ve never landed a superstar free agent (the closest signing being George Springer).

Entering the final season of Vladimir Guerrero Jr. and Bo Bichette’s deals, the Blue Jays have to be ultra-aggressive in acquiring players if they wish to contend. They have to be the highest bidders for Juan Soto, and if that falls through, they have to use the “special budget” they have on him for other needs.

There needs to be a pivot in place if Soto signs elsewhere, whether that being signing two big bats and an ace starting pitcher, or a big trade to acquire a superstar, it needs to happen. If there’s even a chance to make the postseason at the trade deadline, Atkins can ill afford to stand pat, they need to go big and acquire players that fill holes.

A few years ago, holding onto prospects for long-term success made more sense, but we’re about to enter the 2025 season and Vladimir Guerrero Jr. and Bo Bichette have yet to win a postseason game before they’re set to enter free agency at the end of the season. It’s time for the Blue Jays to be in “Flags Fly Forever” mode.

<hr />

As always, you can follow me on Bluesky @ryleydelaney.bsky.social.

The Blue Jays have to be in “Flags Fly Forever” mode in 2025

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