Advisor to Ontario Education Minister Gerrard Kennedy After graduating from university, Telford joined the staff of
Ontario Liberal MPP
Gerrard Kennedy as his legislative assistant, starting working coincidentally on the day of the
September 11 attacks. Kennedy's office was sensitive terrain at the time for a number of reasons. In the
preceding leadership contest, Kennedy was the charismatic frontrunner who led through the first four ballots before being defeated by fourth place contender
Dalton McGuinty. Despite being the incumbent MPP for
York South, Kennedy was pressured to yield the new
York South—Weston seat, consisting 81% of his former constituency, to neighbouring MPP
Joseph Cordiano, the leadership rival who delivered the final blow to his leadership bid, and was re-elected with an impressive 10000 votes margin in
Parkdale—High Park, encompassed only 19% of his former territory, against another leadership rival who defected to the governing Progressive Conservatives. With the Ontario Liberals having lost the
provincial election in June 1999 after leading in polls for much of the final months of the previous legislature, McGuinty handed Kennedy the high-profile education portfolio in shadow cabinet. Kennedy was named education minister when the Liberals formed government in 2003. In August 2004 just days before turning 26, Telford was promoted to be chief of staff to Kennedy, a notable appointment and an early sign of her calling as senior political aide. She was the youngest ministerial chief of staff at Queen's Park at the time, a rare exception in a new government with many eager veteran aides after over a decade in opposition. Her minister, had a well earned reputation as a demanding high-performer, and was given charge of the education ministry after a decade of labour unrest in the sector under the Progressive Conservatives. During Telford's tenure as Kennedy's chief aide, the McGuinty Liberals delivered their 2005 "education budget" designed to tackle the structural deficits in the education system. Kennedy established that same year a province-wide negotiating framework with the province's teachers' unions with the result that most
school boards settled their contracts without lost teaching time, and announced that 90–95% of Ontario students between junior kindergarten and Grade Three would be in classes of twenty students or fewer by 2007. Telford later credited Kennedy for her widely known data-driven approach to political campaign and her "obsession" with data. During her time at Queen's Park, Telford also developed a close working relationship with
Gerald Butts, policy secretary and then principal secretary in McGuinty's office, with whom she would share the top rank in the Trudeau's
Prime Minister's Office a decade later, .
Kennedy's Federal Liberal Leadership Bid In April 2006, Kennedy resigned as education minister and declared his
candidacy for the leadership of the
Liberal Party of Canada. Telford left his position in Queen's Park to manage Kennedy's bid, She returned to Toronto between her positions with Dion and Trudeau, working as a consultant for StrategyCorp in Toronto, These expenses included a personalized cash payout of $23,373.71. After it was revealed publicly, Telford agreed to repay a portion of the $80,382.55. Telford's political influence and authority over the government and the liberal party were further elevated following the February 2019 resignation of the
Principal Secretary to the Prime Minister Gerald Butts, a personal friend of Prime Minister Trudeau since university days and Telford's close ally and former colleague in the Ontario
McGuinty ministry. Prior to the departure, it was generally accepted that Telford and Butt were of equal stature as the highest-ranking aide to the prime minister and were co-leader of PMO. No other principal secretary were appointed for the remainder of Trudeau Premiership. Instead, Telford named two deputies, Brian Clow and future Health Minister
Marjorie Michel, and remained the sole occupant of PMO highest rank until Trudeau's resignation in 2025. In 2020 and 2021, then Conservative finance critic Pierre Poilievre on multiple occasions alleged that Telford's husband Rob Silver engaged in unlawful unregistered lobbying activities on behalf of his new employer MCAP, a non bank-owned mortgage finance company. It was alleged that Silver participated in meetings and discussions with officials in the
Prime Minister's Office,
Department of Finance and federal crown agency
CMHC that lead to CMHC's decision to outsource the administration of the federal government's COVID-19 emergency rent assistance for small businesses and awarding the contract, worth up to $84 million, to MCAP. In response the
Prime Minister's Office noted that Telford proactively reached out to the
Conflict of Interest and Ethics Commissioner and the
Lobbying Commissioner for direction and set up a voluntary ethics screen before MCAP was awarded the contract. This allegations against Silver was investigated by the
Lobbying Commissioner, who cleared him of any wrongdoing. Telford testified to a House of Commons committee regarding
sexual assault allegations in the Canadian Armed Forces and the
WE Charity scandal. Telford has also been called by members of the media and opposition parties to testify about alleged
Chinese interference in the 2019 and 2021 federal elections, as of March 2023. Telford was also influential in Canada's response to the COVID-19 pandemic, and the negotiations of the Liberal-NDP
supply and confidence agreement. ==Personal life==