I’m really shocked Rafael Montero hasn’t been mentioned yet. His 22 season was such an anomaly, and it’s crazy to think that he got $11.5 million a year for only one good season.

I am really OK with not hearing more about Al Avila and the Tigers making bad trades

A player I'd like to see in a potential part 3 would be Ian Desmond. Went to the Rangers in 2016 putting up an all-star season for them, and in the 2017 off-season signing with the Rockies and proceeds to put up negative WAR seasons in his final 3 yrs.

not like papa 😭😭😭 too soon Jack, I still haven’t recovered

9:09 Ayyyy, that's me! Yeah, people always talk about the Rays making good trades, but I'd say 'signing journeyman players to one year deals and getting career years out of them' was the real secret to the Rays 2010s success, and Keppinger (and Casey Kotchman, to be fair) is the poster child of that. I wanted the Rays to resign him too, how young and foolish I was lol.

I will be excepting a statement apologizing for that Marco Estrada joke

Seeing Dylan Bundy's name alongside Cashner's makes me think you need to do another lopsided trades video if only to marvel at the fact that the Orioles somehow got anything of value for Bundy and a potential ace in Kyle Bradish at that.

Milton Bradley with the 2008 Rangers is even more confusing in hindsight than the Matthews one.

his best season was with the cubs. never been the same since.

I always think about how Milton Bradley got paid 10 mill a year after a break out 5 WAR year after some mediocre seasons and then became a negative asset both on the field and in the club house before everyone finally collectively gave up on him

1993 might be before your time but these really hurt:

Robby Thompson and Kirk Manwaring of the Giants.

Had insane walk years, Giants reward these long time Giants with a second contract. They go back to what they were before 1993... while letting Will Clark walk over 2 additional season on the contract the same offseason.

Will Clark was my favorite player and the franchise player before the current ownership group took over. After saving the team from moving to Florida they signed Barry Bonds, the best contract ever value wise in my opinion, and after his first season dealing with injuries they let the old face go but kept the two weak hitting defensive players that had career years.

I indeed had never seen that Mets legend Gary Matthews catch before jolly thank you

Rockies signing Wade Davis and Ian Desmond. Hell, add Kris Bryant in there now.

I've always been convinced that the Angels paid Gary Matthews based entirely on that one catch.

As a Phillies fan one thing I’m looking forward to seeing the most in 2026 is actually good defense in right field. Having someone who can make a strong throw is super underrated. I place a lot of value on a strong arm in right. Castellanos has been horrible to watch I’ve wished he was off the team since 2024.

The fact Andrew Cashner was drafted four times is crazy.

jfc that Tigers WAR return graph would give me nightmares if I were a Detroit fan

5:52 Why is my boy Marco Estrada catching strays?

I will never forgive Bill Bivasi and Jack Zduriencik for the damage to the Mariners.

Castellanos is a class act. Always interacting positively with fans in Philly outside the stadium. It’s a shame play has gone downhill on the diamond , but I will always have respect for the dude.