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Former Springfield principal chosen to head troubled Madison Park High

Kevin McCaskill’s hiring comes amid several problems that Madison Park has weathered in recent years. Jonathan Wiggs/Globe Staff

The interim superintendent of the Boston public schools has tapped a former principal in Springfield to lead turnaround efforts at the Madison Park Technical Vocational High School in Roxbury.

Kevin McCaskill, 53, former principal of the Roger L. Putnam Vocational Technical High School in Springfield and a Hartford administrator, will take over as executive director at Madison Park on July 1, the School Department said in a statement.

“I really look forward to making this school the true jewel of the Boston public schools,” McCaskill said in an interview.

His hiring comes amid several problems that Madison Park has weathered in recent years, including the resignation of the school’s former headmaster, Diane Ross Gary, in September 2014 after officials learned she did not have proper certification.


Gary had also come under fire for a scheduling issue that left many students and teachers at the city’s only vocational high school without classes. The flap over Gary’s credentials was the latest blow to the school, which has been plagued by low standardized test scores and graduation rates.

Earlier in 2014, a School Department intervention team recommended that Madison Park be shut down in three years unless there was dramatic improvement.

McCaskill said Tuesday he had no reservations about his new post.

“None whatsoever,” McCaskill said. “I think with hard work, dedication, and a collaborative effort, we can really do some great work there.”

McCaskill, though praised by former colleagues in Springfield and Hartford, has faced his own professional challenges.

In 2011, auditors found that Putnam School employees had used school funds to purchase equipment for their personal use, among other financial irregularities between 2002 and August 2010.

McCaskill, who served as principal from 2004 to 2010, was not implicated in any wrongdoing, but four employees were fired.


“It happened on my watch,” McCaskill said. “I take full responsibility for not putting in stricter accountability measures for this school. I was not part of any underhanded [practices] or double dealing or anything that could be an advantage for me. . . . It was a disgrace. It was something that should not have happened.”

McCaskill also faced scrutiny in 2008, when he called an assembly at Putnam to warn students about pulling false fire alarms, after two alarms were set off on the same day. He told students that he would “crack your hand” if he caught them touching a pull switch, according to McCaskill and a report from the Springfield Republican newspaper.

Alan Ingram, who was the city’s superintendent, said through a spokeswoman after the incident that he had “full confidence” in McCaskill, the newspaper reported.

On Tuesday, McCaskill conceded that he used a “poor choice of words” and said he would “not even think about harming any children.”

He said he wanted to convey to students the seriousness of pulling false alarms.

The veteran educator has also had personal financial troubles, he disclosed on Tuesday. McCaskill said creditors sought to collect debts from him about a decade ago that exceeded $1,000, though he could not recall the precise figure.

“All those debts were paid in full,” McCaskill said. “This will in no way, shape, or form impede my ability to be a good fiscal steward of Madison Park.”

John McDonough, who steps down as Boston superintendent on July 1, hired McCaskill after a six-month search that included roughly 30 applicants who were vetted by a committee of community leaders, students, and educators, the School Department said. His salary is being negotiated.


“I have every confidence that Mr. McCaskill will lead Madison Park in a direction that will realize the vision we all share for this vital school,” McDonough said. Incoming superintendent Tommy Chang was not available for comment.

Mayor Martin J. Walsh said McDonough and the hiring panel “strongly believe Kevin is the right person for the job. I hope to see great academic improvements at Madison Park with a new leader in place.”

Deborah Cox, a Madison Park parent who served on the hiring committee, said the panel believed that with McCaskill, “we were getting somebody who really would respond to the needs of our community.”

“We recognized there was some baggage,” Cox said “I was just overall impressed with his vision and what he brings with his breadth of experience.”

McCaskill has served as an administrator in the Hartford Public Schools since July 2010.

On Tuesday, officials in Hartford and former colleagues in Springfield praised his work ethic, including Janine Lapan-Yawson, a former English language arts teacher at Putnam.

“He’s actually a dynamic human being,” Lapan-Yawson said. “He’s able to build relationships with students and parents, as well as the staff that works under him.”

James Vaznis of the Globe staff contributed to this report.