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We’re halfway through the MLB season, and you, dear reader, have no doubt been scoring along at home, tabulating the wins, and rooting for Dennis to defeat Josh in their 2021 Team Draft. You no doubt know that Dennis leads Josh 476 to 471 in this hotly contested match up that is gripping the nation. To add to your enjoyment, The Prompt’s Baseball Boys are here to provide their thoughts on their picks at the midway point, and, more importantly, engage in a late summer baseball tradition: trade deadline maneuvering.

Each competitor will be permitted to trade two of their teams. Only the post All-Star Break wins will count towards the win totals. A new team’s current wins won’t retroactively—you don’t care. Josh and Dennis get the rules, that’s all that matters.

Trade Number One


I took the Orioles to be cheeky and cute, since it was generally believed that they had a -6 percent chance of making the playoffs. While they did sweep the Boston Red Sox to open the season, it’s been downhill since then, and I’m dumping them for the other orange and black team: San Francisco, who are spitting in Father Time’s face.


There’s two ways to handle this trade. One is to get rid of the team with the lowest number of wins so far. The other is to try to use my “baseball knowhow” and think about what team will win even fewer than they did in the first half. I must trust the knowledge and instincts that got me to second place in this contest between two people and trade the Cubs, who will likely be sellers at the trade deadline. Goodbye Cubs. Hello Mariners.

Trade Number Two


I want to get out of the Twins baseball business as soon as possible. They won the division the last 2 years and have embarrassed themselves, and me. I will trade this 39-win team for another 39-win team because I am a fair, embarrassed guy. I’ll take the Miami Marlins, and their bright future. I just hope that this bright future starts immediately.


I will be standing pat and not making a second swap. Is this a lack of creativity, or a flex of confidence? Only time will tell.

Dennis’ Teams

Dodgers (56 wins):

I watched two innings of a Dodgers game the other day and saw them hit eleventy home runs. I’m so smart for taking them first.

Yankees (46 wins):

Josh could have had the Yankees, but he took the Braves. I am two wins smarter than him, and 27 times filthier in my soul for sharing a rooting interest with Dominic from Yonkers.

Padres (53 wins):

Other than the Royals, a team that the roulette wheel of fate and geography has bound me to, San Diego is the team I’ve watched the most, and it’s for three reasons: former Royal Eric Hosmer, Fernando Tatis Jr., and Yu Darvish’s hair.

Astros (55 wins):

Apparently they’re still very good, even without the sound effects. Frankly, I forget that I’m supposed to care if they win.

Mets (47 wins):

In 1998, the Mets acquired Mike Piazza, a player I liked. That was enough for me to try rooting for them, having lost all patience for a team that would employ Brent Mayne for 6 years (as opposed to the one he spent with the Mets). That dalliance is finally paying off.

Angels (45 wins):

Do you think Ohtani is single? Has he mentioned me?

Brewers (53 wins):

I’d like to think I knew that Milwaukee would be leading the NL Central, but I know deep down that I chose them because their uniforms, stadium, and city are all dope.

Blue Jays (45 wins):

This team mashes, which is fun. But not as fun as hearing their color commentator, who sounds like the ghost of Harry Caray, saying Cavan Biggio’s name.

Reds (48 wins):

Baseball Twitter tells me that Joey Votto is fun and cool. I’m not enamoured. But the Red’s 48 wins are pretty cool.

Giants (57 wins – 0 Dennis wins):

Neither of us drafted the team that currently possesses the best record in all of MLB. I’d be pretty embarrassed if I worked for some sort of sports media outlet instead of a public school.

Josh’s Teams

Braves (44 wins):

This was my first pick? Are we sure? Was I in a COVID fog? I guess there’s still hope they figure out their pitching and don’t miss the most fun non-Ohtani/Tatis player in the league.

White Sox (54 wins):

Nailed it. I never miss on these picks.

Marlins (39 wins – 0 Josh wins):

Fun fact: Young Josh loved expansion teams. In 1994 I was big into Marlins teal.

Nationals (42 wins):

Well if a 42 win first half is majorly disappointing, put me down for a tall glass of hope.

Athletics (52 wins):

I said it when I picked them, but the A’s win 90 games every year in the worst division in baseball. Sometimes I need to remember not to overthink things.

Rays (53 wins):

Very pleased with the A’s, Rays combo that piles up wins and scares nobody while doing it. I still can’t name three guys on the Rays’ pitching staff.

Cardinals (44 wins):

I don’t even mind that this team is underachieving. The only thing better than 44 wins for this team would be 0.

Red Sox (55 wins):

I will not say anything brash about this pick. I will continue to pretend that this is exactly as I expected it. I will not jinx anything here because jinxes don’t work and the universe operates the way it does.

Phillies (44 wins):

If this team could hold a lead it would be a very good baseball team. It is not a very good baseball team.

Mariners (48 wins – 0 Josh wins):

I don’t think Ken Griffey is coming back this year, but I like the upwards trajectory I’m seeing.

With the teams realigned and the starting rotations reset for the second half of the season, only one of the baseball best friends can come out on top. Cheers to more Ohtani, less sticky stuff, and the same great amount of Yankees losing.

The Prompt Staff

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