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1. How many JC units can be transferred to a D1 school, acquired as a HS student?
Depends on the school. The NCAA will accept the credits, if they do appear on the JC transcript, but don't appear (I believe) on the high school transcript.
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2. If he does graduate in the fall, takes a full load (15 units) would that negatively effect his eligbilty as a player at a 4 year college?
Yes, it will affect his eligibility, because of the 5 calendar year rule. A full load in this context is probably 12 hours, even if the JC defines it as 15. Taking 12 hours or more at the JC does two things. 1. It will make him a transfer student. No problem unless he ends up dropping a class or has some other event that gives him less than a 2.0GPA at the JC. 2) It starts the 5 year calendar in January 2010. That means that he will only have 4 calendar years at the D1 school in which to play baseball. So if he attends the JC full-time in Spring 2010, transfers to D1 in the fall of 2010, then his eligibility ends just before spring 2015. In other words, the spring 2014 season would be his last possible season. If he happens to suffer an injury which keeps him from competing for one season, then he would only be eligible for 3 seasons.
Important! Both 1. and 2. could lead to becoming a non-qualifier. For ordinary qualifier status, he needs 16 core courses, and 4 years of English. If he graduates early, then he won't have the 4 years of English. Even if he doesn't graduate early, but does take mostly JC courses, he may inadvertantly miss the core course requirements, unless the JC courses are the right ones, and they appear on his HS transcript. In either case, he can, however, make use of 14.3.1.1.1 Exception—Early Academic Certification. Roughly, that means 13 core courses (3.0 GPA) during the first 3 years of high school, and 1000 on the SATs. Simply graduating from HS is not enough, even though it may be obvious that he is a very good student. If he doesn't meet the detailed official requirements to be a qualifier, he'll either need to sit a year when transfering to a D1, or get an AA degree at the JC. Look carefully at 14.3.1.1, and visit the Clearinghouse website to make sure that your son has for sure taken certified core courses. Sometime the high school may have failed to declare some courses as core, so you really need to check this, since he may be on the ragged edge of having sufficent courses.
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3. What is a gray shirt?
As used on the HSBBW, it simply means to avoid starting the 5 year clock. A player does that by taking less than 12 hours at any college when initially entering college, or in the extreme, not entering college during the semester or year after high school graduation. If he enrolls for less than full-time at a D1, he can't practice, but typically can practice (but not play) if enrolled part-time at a JC.
In football, or other fall sports, it is possible to enter college full-time in the spring, and not suffer any ill consequence. The 5 year clock starts, but football season is over before the clock runs out. In the example above, a football player would have the 5 seasons of fall 2010 through fall 2014 in which to get in his allowed 4 seasons of competition.
It is a poor plan to initially enroll full-time at a JC if the player knows that he isn't going to compete in baseball that year.