Aug. 15, 2023 | Detroit Red Wings Acquire:  Jeff Petry ($2,343,750 retained - 50%) · $2,343,750$2,343,750$2,812,500 Sum: $2,343,750$2,343,750$2,812,500 Change: +$1,393,750 Change: +$1,393,750 Change: +$1,862,500 |  | Montreal Canadiens Acquire:  2025 4th round pick (DET) [Conditional]* *Conditions: Montreal receives the later of Detroit or Boston's 2025 4th round picks Sum: $950,000$950,000$950,000 Change: -$1,393,750 Change: -$1,393,750 Change: -$1,862,500 |
| Aug. 6, 2023 | Montreal Canadiens Acquire: From PIT: Jeff Petry ($1,562,500 retained - 25%) · $4,687,500$4,687,500$5,625,000 2025 2nd round pick (PIT) Sum: $6,487,500$7,276,667$7,595,000 Change: +$887,500 Change: +$1,676,667 Change: +$1,495,000 | | Pittsburgh Penguins Acquire:  From SJS: Erik Karlsson ($1,500,000 retained - 13%) · $10,000,000$10,000,000$10,000,000 2026 3rd round pick (SJS) From MTL: Sum: $11,100,000$11,889,167$11,170,000 Change: -$3,137,500 Change: -$3,137,500 Change: -$4,925,000 | | San Jose Sharks Acquire:  From MTL: From PIT: 2024 1st round pick (PIT - #14) [Conditional]* *Conditions: Top 10 protected Sum: $12,250,000$12,250,000$13,500,000 Change: +$2,250,000 Change: +$1,460,833 Change: +$3,430,000 |
| Jul. 16, 2022 | Montreal Canadiens Acquire: Sum: $4,875,000$4,875,000$4,000,000 Change: -$2,125,000 Change: -$2,125,000 Change: -$4,250,000 | | Pittsburgh Penguins Acquire: Sum: $7,000,000$7,000,000$8,250,000 Change: +$2,125,000 Change: +$2,125,000 Change: +$4,250,000 |
| Mar. 2, 2015 | Edmonton Oilers Acquire:  Sum: $0$0$0 Change: -$3,075,000 Change: -$3,075,000 Change: -$3,075,000 | | Montreal Canadiens Acquire: Sum: $3,075,000$3,075,000$3,075,000 Change: +$3,075,000 Change: +$3,075,000 Change: +$3,075,000 |
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