No transition between MSSD Directors
McGregor walks out after heated exchange with Board
Transition proposal leads to disagreement
By Logan Watson
In addition to hiring a new Director of Schools, the Milan Special School District Board of Education attempted to address the transition period between outgoing Interim Director Judy McGregor and incoming Director of Schools Jonathan Criswell, which caused a rift between McGregor and the Board.
An audio recording of the meeting can be played below.
The transition was addressed Thursday night following the approval of Criswell’s contract by the Board. According to both Criswell and McGregor, the pair had discussed McGregor’s transitional duties and reached an agreement before presenting their proposal to the Board.

NO TRANSITION – MSSD School Board member Greg Horton and others voted last Thursday night to table the proposal that would have established a transition period between former Interim Director of Schools Judy McGregor and newly hired Director Jonathan Criswell. The vote effectively ended McGregor’s employment with the District and left Criswell with no assistance moving forward into the school year. Chairman Crocker told the Mirror-Exchange that McGregor would advise Criswell as a personal favor, but would not be doing so through the MSSD. File photo by Logan Watson.
The agreement included a one-month period, from August 1 to August 31, during which McGregor would work with Criswell to help him transition into his job, estimated at 160 hours at her previous contract rate of pay. From September through December, McGregor would work with Criswell and the MSSD staff “in developing the District Five Year Plan, District Improvement Plan, School Improvement Plans and any other duties as needed.” McGregor’s would work approximately 172 hours throughout the transition period at $50 per hour.
According to the document, the proposed transition plan was developed along with Finance Director Shannon Petty in order to make sure the amount paid would fit within the budget.
Even though McGregor and Criswell had worked together on the proposal, the relatively simple document was met with resistance by some Board members. Greg Horton stated that he felt the transition period was too long, recalling a brief discussion that the Board had with Randall Bennett of the TSBA when the search for a new director began. Horton said that Bennett had suggested a two-week transition period, when in actuality, Bennett had initially told the Board that he felt the transition period should typically last no longer than six weeks.
Criswell, who was in attendance at the meeting, told the Board that the proposed transition period would help the MSSD meet the upcoming state requirements that McGregor had already been working on before he was hired.
Board Chairman Sid Crocker added that the transition plan would also solve a problem with McGregor’s insurance coverage. If the Board were to release McGregor before the end of the year, she would lose her coverage, but she clarified that insurance had no bearing in the way the two had arrived at the proposal.
“There will be things coming due in the next few months that would be easier for him if he had my input,” McGregor told the Board.
Missy Ross added that she felt that the Board should table the issue until Criswell had time to get adjusted and look into the Five Year Plan and other items rather than potentially waste money. Horton also questioned why the transition plan was not brought to the Finance Committee.
“They figured up the hours based on what they thought was appropriate,” said Chairman Crocker. “If something changes down the road, they can come back and reduce the hours or extend them.”
Citing the uncertainty of Criswell’s needs, Yolanda Lett made a motion to table the transition duties proposal. Horton seconded the motion. Vice-Chair Hensley agreed, stating that she did not feel the period should be set all the way through December.
“I just want to make sure Mr. Criswell is comfortable with everything,” said Ross.
“Did you see his signature on there?” McGregor retorted. “We’ve been talking about it. He hasn’t been here until today.”
The discussion drew the ire of McGregor, saying, “Three thousand dollars is gonna break y’all? Forget it!”
”Three thousand dollars has nothing to do with it,” said Ross. “I apologize. I’m sorry you’re getting your feelings hurt…”
“No you’re not!” McGregor replied indignantly. McGregor then asked Lisa Springer to unlock the door to the office hallway and left the meeting.
After the room settled, Chairman Crocker stated that if the Board did not handle McGregor’s contract at that time, the MSSD would have two directors under contract. Horton added that the Board had already voted to approve McGregor’s contract through December, so they would be covered for the transition period, telling Criswell that his disapproval of the proposal was not a reflection upon him, but that transitions, in his experience, should be “short and sweet”.
The motion to table the transition proposal was approved by a vote of 5-1, with Chairman Crocker voting against the measure. Board member Marty Elliott was absent.
Chairman Crocker confirmed Monday morning what many had been wondering since the exchange between McGregor and the Board.
“As of right now, Mrs. Judy will not be returning to assist with the transition,” Crocker said, stating that McGregor felt insulted and undermined by the Board. “That may change in a week or two, but it doesn’t look good.” According to Crocker, McGregor contacted Criswell following Thursday’s meeting and told him that she would be willing to meet with him to help in any way he needed, but she would not be doing so through a contract with the MSSD.