Remember two years ago?
The two top prospects in baseball were Jackson Holliday and Jackson Chourio; the 12th-best prospect was Jackson Merrill, and the 25th-best prospect was Jackson Jobe. However, the title of this blog is The Three Jacksons, so we are going to pretend like Jackson Jobe doesn’t exist.
All three franchises believed they had their cornerstone for the next decade. Two of them went and locked their men up (go look at the Chourio deal, it’s hilarious.)
After two years, I think we have enough of a sample size to play an appropriate game of F-K-M, that is, kid-friendly, of course. The three categories will be Firm Handshake, Kick Into The Sun, and Marry.
To be clear, this is strictly based on what they are doing on the field, nothing else.
Firm Handshake: Jackson Merrill
Over 341 career games, Merrill has posted a .265 batting average, .313 OBP, and .455 slugging percentage (.767 OPS). In his 1,262 at-bats, he's tallied 335 hits, 48 home runs, 187 RBIs, 168 runs scored, and 29 stolen bases, accumulating 7.9 WAR.
Merrill came out of the gates hot and ended up in the Top 10 of MVP voting in 2024. He had no chance of winning Rookie of the Year with Paul Skenes making his debut, but San Diego thought they had a perennial MVP candidate on their hands.
Then, well, 2025 happened, and Jackson battled injuries, playing only 115 games. He was still productive, and many gave him the benefit of the doubt coming into 2026. So far, he has regressed more and really started to make men like me wonder what his future holds.
San Diego has him locked up through 2035 on a non-crippling deal.
Right now, I am keeping Jackson as a firm handshake. I will hold the handshake long enough for him to know that there could be a future between us.
Kick Into The Sun: Jackson Holliday
Through 236 career games, Holliday owns a .227 batting average, .298 OBP, and .363 slugging percentage (.662 OPS). In 856 at-bats, he’s collected 194 hits, 26 home runs, 90 RBIs, 111 runs scored, and 24 stolen bases, good for 0.8 WAR.
When Holliday debuted a few years ago, I was genuinely excited. Thankfully for me, he debuted against the Red Sox, so I didn’t have to change the channel to see his debut. If you remember that series, he wasn’t great. Offensively, he was chasing; defensively, he was all over the place, and you could tell that Fenway was eating him up. Frankly, it seems he never broke out of that funk. He had an abysmal April and didn’t improve much when he returned later in the summer.
In 2025, he was “eh”. Better against righties, still couldn’t do anything against lefties, and battled some injuries. Started 2026 on the IL after hamate surgery, so his sample size right now is too small to judge.
Baltimore is the one team on this list that did not lock up Jackson in a long-term deal. They are looking pretty bright right now for that.
At the moment, I have to throw Holliday into the sun. His defense is bad; he can’t run the bases; his offense is bad; and he was by far the most hyped prospect.
Marry: Jackson Chourio
In 317 career games, Chourio is slashing .277/.323/.476 with a .799 OPS. Across 1,240 at-bats, he has racked up 343 hits, 52 homers, 185 RBIs, 196 runs scored, and 48 stolen bases, matching Merrill with a 7.9 WAR.
Chourio started his career with consecutive 20/20 seasons. His 2024 was good, but it was a good bit behind Merrill’s. Now, if you are looking at their career numbers, they are pretty freaking close. But what gives Chourio the edge is that he has consistently gotten better over the last three years. Whereas Merrill has regressed and Holliday never existed, Chourio took the adjustments pitchers made for him and actually countered them.
I know I said I am only taking on the field performance into account here, but sometimes you have to think about the money. Milwaukee can have him locked up until 2033 for pennies on the dollar. His 8-year $80 million deal is highway robbery.
I feel pretty confident in marrying Chourio. Yes, once in a while, I might see Merrrill and think what could have been. However, right now, I have to go with the younger, faster, more well-rounded man.
