| Jul. 1, 2015 | Pittsburgh Penguins Acquire:  Phil Kessel ($1,200,000 retained - 15%) · $6,800,000$6,800,000$8,500,000 *Conditions: If Pittsburgh misses the 2016 playoffs, then Pittsburgh shall receive Toronto's 2017 2nd round pick. If Pittsburgh misses both the 2016 & 2017 playoffs, then Pittsburgh does not receive any pick from Toronto
Result: Pittsburgh clinched 2016 playoff birth. Pittsburgh will receive Toronto's 2nd round pick (PIT) from Toronto. Sum: $7,400,000$8,294,167$9,932,500 Change: +$3,716,666 Change: +$4,610,833 Change: +$7,157,500 |  | Toronto Maple Leafs Acquire:  2016 1st round pick (PIT - #30 - Sam Steel) [Conditional]* *Conditions: If Pittsburgh misses the 2016 playoffs, then Toronto will receive Pittsburgh's 2017 1st round pick. If Pittsburgh misses both the 2016 & 2017 playoffs, then the 2017 1st round pick to Toronto becomes a 2017 2nd round pick
Result: Pittsburgh clinched 2016 playoff birth. Toronto will receive Pittsburgh's 2016 1st round pick Sum: $3,683,334$3,683,334$2,775,000 Change: -$3,716,666 Change: -$4,610,833 Change: -$7,157,500 |
| Dec. 14, 2014 | Chicago Blackhawks Acquire:  Sum: $600,000$600,000$600,000 Change: -$200,000 Change: -$200,000 Change: -$100,000 | | Columbus Blue Jackets Acquire:  Sum: $800,000$800,000$700,000 Change: +$200,000 Change: +$200,000 Change: +$100,000 |
| Jul. 23, 2012 | New York Rangers Acquire:  Sum: $7,800,000$8,385,000$8,200,000 Change: +$1,725,000 Change: +$1,410,000 Change: +$8,200,000 | | Columbus Blue Jackets Acquire: Sum: $6,075,000$6,975,000$6,525,000 Change: -$1,725,000 Change: -$1,410,000 Change: +$6,525,000 |
| Jun. 1, 2011 | Calgary Flames Acquire:  | | New York Rangers Acquire: |
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