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Reply to "when to go into portal- D1 ?"

A kid in your situation now has to sell himself based on his recruitability from high school. Note that, if the original commitment was made prior to his senior season in high school, a lot may have chnged. If for the good, his position may well look better than it did when he was originally being recruited. My own son's baseball stock was considerably higher when he was facing the decision to enter the portal after a redshirt freshman year than it was during the summer of his junior year. Unfortunatley, his problem was academics which followed him to JC. Now, after having limited time on the mound due to covid last season and sitting out this season to work on his grades, he decided he wanted to play again. He treated it just like original recruiting except he now had to explain the past two years. The first email he sent was answered within 15 minutes. Keep in mind, though, that this is D2 (he can't pass the transfer requirements of D1). The point, however, is, a kid in his situation has to resell themselves and find a way to do so based on his position as a high school senior. Difficult waters, but totally navigatable. Here's a redacted version of what worked for my 2018:

Coach X,
  I'm a 21yo pitcher looking for a second chance. I was an All-American out of Lamar, CO high school who signed with CSUN to play Big West baseball. Things didn't go well for me in California. I had trouble adjusting, was miserable in L.A. and fell into academic problems. After redshirting the 2019 season, I moved home to Lamar and attended Lamar Community College. A few games into the season, covid hit. I again experienced academic problems, failing to adjust to online learning schedules. The following fall I was again not doing well in school and quit baseball to concentrate on my academics for the Spring semester. I've turned the corner and will be receiving my A.A. after completing one more class in the Summer. I'm not sure how much eligibility I have remaining, but given the circumstances, I would guess at least three years.
  Out of high school, I was throwing a consistent 91-93 mph, topping out at 94. As of last fall, I was still consistently in the low 90's. I'm keeping in throwing shape and believe there are a few more mph's I can gain. I have moved to X CITY for a summer job and would love to talk to you and your staff if you think you might be interested in having me for next season. I am including links below to my accomplishments and several game videos edited to show only my pitches in a compact form. PLEASE feel free to call me if X UNIVERSITY might be interested. I'd love an opportunity to play for you.
Dalton Chandler
719-xxx-xxxx
Some of my accolades (all are listed on Questionnaire):
High School coach: Dave Fassiotto   719-688-xxxx / dave.fassiotto@lamarschools.org
High School coach: Jason Veyna 719-336-xxxx
Summer coach: Scott Boyd  720-351-xxxx / sboyd@qualitypipeservices.com
Game video:
Plenty more available on youtube (search: Dalton Chandler baseball Lamar) 
Attachments area
Preview YouTube video Dalton Chandler 2018 RHP vs. La Junta 4/26/18 Part 1
Dalton Chandler 2018 RHP vs. La Junta 4/26/18 Part 1
Preview YouTube video Dalton Chandler 2018 RHP vs. Lutheran 2018 State Playoffs
Dalton Chandler 2018 RHP vs. Lutheran 2018 State Playoffs
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