The forward can become a free agent in July if he declines his $21.3 million option for next season.
Per Lewenberg, the Raptors' pitch will be about "trust, familiarity, a commitment to maintaining his health and the shared goal of chasing a championship, as well as the extra year and contract worth nearly $50 million more than anyone else can offer."
Toronto will be able to offer a max contract of $190 million over five years, while another team would only be able to offer $141 million over four years.
Money aside, things have seemingly gone well for Leonard in his first season with the team since an offseason trade from the San Antonio Spurs.
The 27-year-old is averaging 27.2 points and 7.5 rebounds per game, both of which would be career highs if he maintains it for the rest of the year. He has also helped the squad to a 51-23 record entering Monday, good for the second-best in the NBA behind only the Milwaukee Bucks.
While the postseason could potentially determine his enjoyment this season, the Raptors have seemingly done as much as they can to keep his spirits high so far.
Considering Paul George re-signed with the Oklahoma City Thunder after it was highly speculated he was headed to Los Angeles last offseason, Toronto shouldn't count itself out in the Leonard sweepstakes.