Discounting any particular trade value received, the previous five first round picks really didn't do much of anything for the organization at all. It seems like that really should be about rock bottom, doesn't it? I mean, how much lower can you go?
I'm not sure it's really that wise to ask, but now that we've gone and on it let’s take a look at how the team’s next five first round picks turned out.

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Dalton was draft straight out of high school, and spend several seasons throwing some decent ball through the Phoenix farm system. He showed up on the parent team's roster as a 23 year old and stayed there until he was 25, at which point he move to Rome to play in the EBA. He finished his career as a pro baseball player with a 1-season stint back in the BBA minor league system. His 26 inning, 3.42 ERA was his best season as a Talon/Nine, but was quite effective as an EBA'er.
He retired to start a flooring business, and spent years on a legal case involving an alleged stiffing of contractors.
Draft Assessment: Saying your first rounder was highly effective as an EBA'er is not good.
Value Achieved for YS9: Minimal.

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Raines played seven seasons with Des Moines because, of course, he was traded. On the "positive" side, with the exception of 2017 he really wasn't much more than a replacement level guy for the Kernels. He did manage to capture that magical single season, though, a 33-homer, 101 RBI stint that saw him register 3.4 WAR. We understand his mother stitched these numbers into some quiltwork she was doing, and that the piece currently resides in the Christian Raines Museum in Tucson, Arizona, where Raines hails from.
Bottom line: fairly decent defensive corner outfielder who didn't totally kill rallies with the bat. Whatever value he had went to another franchise, though. In other words.
Draft Assessment: How many 5th outfielders do you want to draft in the first round?
Value Achieved for YS9: None

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Guerra started 97 games for the franchise, and was on the roster when it moved to Yellow Springs, where he had arguable his best season, going 10-10 and posting a 3.88 ERA. This achievement could not stand, so he was traded to Buffalo in mid-season. He went on to have an 18 season career, winning 143 games (180 losses). He was a bit of a workhorse at times, throwing more than 190 innings ten times. His good control was offset by a propensity to give up the long ball, which he did 405 times.
Counting the move from Phoenix to Yellow Springs, Guerra called eight BBA cities home at one time or another. "He was a real vagabond," one historian recalled as he sipped bourbons on the rocks.
Draft Assessment: Decent player
Value Achieved for YS9: Okay

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Break up the Phoenix draft squad, because something astounding happened here. Cruz was drafted in 2009 and actually appeared in games with the parent club that year. He split time between the majors and the minors for two seasons, and then patrolled the team's center field with some pretty good effect for six years before being traded to Carolina.
During those six seasons he occasionally found himself on the league's leader boards for games and plate appearance. He led the league in hitting once, and in doubles twice (and was runner up a third time). He currently sits at #5 on the team's career OBP list. #9 on it's doubles list.
Draft Assessment: A real player!
Value Achieved for YS9: Very Good!

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With last year's presssure hanging over them, the team drafted another kid this year that they brought straight to the bigs. Rollins was never particularly solid with the bat, but man the kid had leather coming out his wazoo. A true pitcher's best friend. He was a great teammate, too. A total spark plug who lead by example.
He played parts of six seasons with Phoenix/YS, creating a .251 career batting average and getting on base at a respectable .334 rate. Hit nine homers one year, eight one other time. As best anyone can tell, an injury took him down in 2015, and he was never the same.
Finished his career in Europe.
Draft Assessment: Good player
Value Achieved for YS9: Good

Overall assessment:
The drought continued for two seasons, then came Guerra, who wasn't a total embarrassment, and then Cruz and Rollins. Yes, fans were seeing an influx of value coming to the team directly through the draft. This makes me hopeful for future episodes.