After I made the list I asked the same question to myself but still came to same conclusion.
Some reasoning:
Phil Acton - Came to the Brook from Florida around '79 or '80 and turned the mindset of the program into a winning program in '83 and has never had a losing year since. Raised the bar year after year until it became a perennial power. He retired after I believe 24 years at BHS and turned the program over to Ivlow. Acton is still involved with the program to this day. IHSA Hall of Famer.
Greg Williams - Player of the year in Illinois in '93. All American and in my opinion the best player ever at the Brook. Switched over to Safety at North Carolina and over the course of a few years contributed to one of the top 5 defenses in the country. Spent some time as a Pro and now assistant coach with San Diego Chargers.
Todd Howard - Top 100 national Player (as was Antoneo Harris the same year) and All Everything in his senior year. Went to Michigan and started at corner for 2 or 3 years. Spent some time in various pro leagues. Howard had a nice playing career but so did a pack of others from the Brook. The thing that gets him monumentalized is his contributions to the program as player AND coach. Nobody has that player/coach combination that Howard does. Great career while playing for BHS and after, but he has also been the Defensive Backs coach for what I believe has been over a decade and has coached up some great secondaries in his coaching capacity.
Now for that 4th spot....
Bailey has obviously done great for Bolingbrook and is an absolute elite talent and a winner. Unfortunately, my opinion is he got short changed at Illinois so doesn't have the history that some others do. I think he might just need more time as his story has still not yet been fully written. I watch him fairly often on ESPN3 playing for Northern Iowa and his week over week improvement has been great to watch. Last week he once again lit it up and was a man among boys leading Northern Iowa over #6 Portland State (which beat 8-4 Washington State earlier in the season) in the FCS playoffs. He will be leading Northern Iowa against 4 time defending champion North Dakota State in FCS quarter finals this weekend. I am a big fan of his but he is just starting to get traction at the college level. He did great at Bolingbrook while he was there but so did Antonio Morrison playing for what has been described as best BHS team ever. Really a toss up between the two based on high school performance or maybe Bailey gets slight edge.
vs Antonio Morrison ....or a host of others.
I have been following Morrison's career at Florida for the past 4 years. The guy has absolutely lit it up in every way since being there (he also lit up Florida State QB EJ Manual who was first QB taken in the 2013 draft). He had some starts as a true freshman and by his sophomore year was full time starter. His Junior year he was All SEC and would probably have been drafted in second round or maybe third round as Junior had it not been for serious injury suffered in a bowl game. He has since come back for his 4th year as Captain of one of the nations best defense. Will probably make some All American lists. Coach Macelwain sites Morrison injury comeback as "The story of the football team". Former Florida Head Coach Muschamp now at Auburn stated Morrison would be his first choice if he could take anybody in the draft. When I was in Florida last year I took a visit to the swamp and Morrison had something like 17 tackles that game. His motor is nonstop and doesnt stop making plays. I watch him on TV and he always has a good game. If Florida had any kind of an offense Morrison could very well be leading the Gator defense in the FBS playoffs and possibly to a National Championship. It remains to be seen where he gets drafted or if his 2 collegiate injuries do or do not affect him at the next level. So I have him on the list because of what he has done but I think his story is not yet fully written either.
Unfortunately for an excellent Bailey, he got caught up in a situation at Illinois that slowed him up a bit while Morrison's path at Florida has really allowed him to shine as a player.