Oct. 8, 2023 | Toronto Maple Leafs Acquire:  2024 5th round pick (VAN - #156) Sum: $0$0$0 Change: -$1,150,000 Change: -$1,150,000 Change: -$1,150,000 |  | Vancouver Canucks Acquire:  Sum: $1,150,000$1,150,000$1,150,000 Change: +$1,150,000 Change: +$1,150,000 Change: +$1,150,000 |
| Feb. 27, 2023 | Chicago Blackhawks Acquire:  2025 1st round pick (TOR) [Conditional]* 2026 2nd round pick (TOR) *Conditions: Top 10 protected Sum: $750,000$1,584,167$880,000 Change: -$2,400,000 Change: -$1,565,833 Change: -$2,270,000 | | Toronto Maple Leafs Acquire: Jake McCabe ($2,000,000 retained - 50%) · $2,000,000$2,000,000$2,000,000 2025 5th round pick (CHI) [Conditional]* 2024 5th round pick (NSH - #151) [Conditional]** *Conditions: If McCabe plays in less than 50% of Toronto's 2023 Playoff games OR less than 25% of Toronto's 2023-24 regular season games, Chicago will transfer their 2025 3rd round pick instead of their 2025 5th round pick.
Result: Leafs will receive Chicago's 2025 5th round pick. **Conditions: The 5th round pick transferred to Toronto will be the lowest of the 2024 5th round picks that Chicago owns at the time of the draft.
Result: Toronto will receive Nashville's 2024 5th round pick. Sum: $3,150,000$3,150,000$3,150,000 Change: +$2,400,000 Change: +$1,565,833 Change: +$2,270,000 |
| Jan. 5, 2022 | Pittsburgh Penguins Acquire:  Sum: $0$874,125$874,125 Change: -$750,000 Change: +$124,125 Change: +$74,125 | | Chicago Blackhawks Acquire: Sum: $750,000$750,000$800,000 Change: +$750,000 Change: -$124,125 Change: -$74,125 |
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