He was a member of the Legislative Assembly of Manitoba for the constituency of Brandon East from 1999 until 2016, serving as a Cabinet Minister in the governments of Gary Doer and Greg Selinger.
When longtime Brandon East MLA Len Evans announced his retirement in 1999, Caldwell defeated Ross Martin and Susan Ferron to win the riding's NDP nomination.
[6] Soon after his appointment, Caldwell implemented an NDP campaign pledge to replace standardized Grade Three language and mathematics exams with individual diagnostic tests administered by teachers.
The network's parent company, Athena Education Partners, had previously offered free technology to schools in return for requiring students to watch daily YNN broadcasts, which included commercials from private corporations.
According to Todd Scarth of the Canadian Centre for Policy Alternatives, YNN televisions were equipped with two-way monitoring systems to ensure that students were watching and that the volume was not adjusted.
[17] Shortly after assuming office, Caldwell told his department to review the Norrie Commission findings on school boards and prepare a report on amalgamations.
[24] Caldwell was forced to cut per-student funding for adult education in 2000, after an unexpected surge in enrollment from the previous year put his department $10 million over budget.
[25] His ministry discovered questionable recruitment practices in the Morris-Macdonald School Division, where cash bonuses had been paid to administrators who brought in thousands of adult students from elsewhere in the province.
[26] An October 2001 report from provincial auditor Jon Singleton found that the Morris-Macdonald board had offered courses of dubious quality, and had overbilled the province by as much as four million dollars by claiming students who were not actually enrolled.
[32] Jon Singleton later discovered that a second school board, the Agassiz Division, had received funding for non-existent adult students in 2001 with the Department of Education's knowledge and approval.
Caldwell acknowledged that his department had made a "foolish mistake" in allowing the transfer, but insisted that it was done to protect students from the consequences of a drastic budget cut.
[34] Following his appointment to cabinet, Caldwell indicated that he would reverse the previous government's changes to the Public Schools Act relating to arbitration for teachers' salaries.
[36] Caldwell's June 2000 legislation expanded the range of arbitrable issues, but did not put teacher contracts under the Labour Relations Act.
[42] Caldwell also introduced a revised funding formula for Manitoba schools in early 2002, simplifying some aspects of a model that was often criticized for its byzantine complexity.
Under his proposals, students would be allowed to earn optional credits through non-traditional means, such as taking part in science projects or performing community service.
Some argued that these changes would devalue the quality of Manitoba education, but Caldwell insisted that the new credit courses would be thoroughly vetted and would incorporate traditional subjects.
[47] The Doer government's first budget, in May 2000, included $60 million of new money for Manitoba's community college system, and a 3.8% increase for university funding.
The Winnipeg Free Press newspaper suggested that he had been "carrying too much responsibility" and "accomplishing too little" in his original ministerial duties, and noted that he was more familiar with the public education file.
[53] In the same year, members of People for the Ethical Treatment of Animals announced that they would distribute trading cards to children outside Manitoba schools as part of a national anti-milk campaign.
The cards showed the unhealthy side effects which PETA members suggested were associated with milk, including an increased risk of cancer and heart disease.
Caldwell refused to allow PETA members on school property, and announced that he would take "appropriate legal steps" if they "entice[d] children into approaching [them] for materials".
[59] In November 2002, Caldwell announced that his government would establish a residential treatment centre to provide care and counselling to sexually-exploited children.
He responded by announcing an overhaul of the child welfare system, and indicated that Manitoba would set workload standards for social workers and supervisors.
This step followed a recommendation by the Aboriginal Justice Inquiry ten years earlier, that First Nations in Canada be given authority for raising their children in the child welfare system.
He became a staunch advocate for the relocation of Assiniboine Community College to the former BMHC site on Brandon's north hill, an initiative commenced during his tenure as Minister of Education.
[74] Caldwell was re-elected in the 2011 provincial election with an increased plurality, and remained the sole New Democratic government MLA in Western Manitoba.