It is almost certainly a lock if he wants it.
Except it isn't. I'll bold the key phrases for you. Remember, this would be a request for a SIXTH year after using a regular redshirt year.
12.8.1.5.1 Waiver Criteria. A waiver of the five-year period of eligibility is designed to provide a student-athlete with the
opportunity to participate in four seasons of intercollegiate competition within a five-year period. This waiver may be granted, based upon objective evidence,
for reasons that are beyond the control of the student-athlete or the institution, which deprive the student-athlete of the opportunity to participate for more than one season in his or her sport within the five-year period. The Committee on Student-Athlete Reinstatement reserves the right to review requests that do not meet the more-than-one-year criteria detailed in this bylaw for circumstances of extraordinary or extreme hardship. A student-athlete who has exhausted his or her five years of eligibility may continue to practice (but not compete) for a maximum of 30 consecutive calendar days, provided the student-athlete’s institution has submitted a waiver request. The student-athlete may not commence practice until the institution has filed such a request. Further, if such a request is denied prior to exhausting the 30-day practice period, the student-athlete must cease all practice activities upon the institution’s notification of the denial.
(Revised: 4/17/91, 1/11/94, 8/10/94, 10/12/95, 8/12/97, 4/27/00, 1/9/06, 7/30/10, 7/31/14)
12.8.1.5.1.2 Circumstances Within Control. Circumstances that are considered to be
within the control of the student-athlete or the institution and cause a participation opportunity to be used include, but are not limited to, the following:
(Adopted: 8/10/94, Revised: 10/12/95, 10/9/96, 7/30/10, 7/31/14)
(a) A student-athlete’s decision to attend an institution that does not sponsor his/her sport, or decides not to participate at an institution that does sponsor his/her sport;
(b) An inability to participate due to failure to meet institutional/conference or NCAA academic requirements, or disciplinary reasons or incarceration culminating in or resulting from a conviction;
(c) Reliance by a student-athlete upon misinformation from a coaching staff member;
(d) Redshirt year;
(e) An inability to participate as a result of a transfer year in residence or fulfilling a condition for restoration of eligibility; and
(f) A student-athlete’s lack of understanding regarding the specific starting date of his or her five-year period of eligibility.