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| TEAM | POSITION | DATE SPAN | AGE SPAN | DURATION |
|---|---|---|---|---|
 Toronto Maple Leafs | Assistant General Manager | Jul 22, 2014 - Apr 12, 2015 | 28 - 29 | 8 Months, 21 Days |
| Toronto Maple Leafs | General Manager (Interim) | Apr 12, 2015 - Jul 23, 2015 | 29 - 29 | 3 Months, 11 Days |
| Toronto Maple Leafs | Assistant General Manager | Jul 23, 2015 - May 11, 2018 | 29 - 32 | 2 Years, 9 Months, 18 Days |
 Toronto Maple Leafs | General Manager | May 11, 2018 - Present | 32 - | 2 Years, 17 Days |
SIGNINGS  | SIGNINGS VALUE | DRAFTED | TRADES |
|---|---|---|---|
| 74 | $411,274,800 | 24 | 36 |
| PLAYER | TEAM | SIGNING DATE | TYPE | LENGTH | CAP HIT | VALUE |
|---|---|---|---|---|---|---|
| Matthews, Auston | Toronto Maple Leafs | February 5, 2019 | Standard (RFA) | 5 Years | $11,634,000 | $58,170,000 |
| Tavares, John | Toronto Maple Leafs | July 1, 2018 | Standard (UFA) | 7 Years | $11,000,000 | $77,000,000 |
| Marner, Mitchell | Toronto Maple Leafs | September 13, 2019 | Standard (RFA) | 6 Years | $10,893,000 | $65,358,000 |
| Nylander, William | Toronto Maple Leafs | December 1, 2018 | Standard (RFA) | 6 Years | $6,962,366 | $45,000,000 |
| Muzzin, Jake | Toronto Maple Leafs | February 24, 2020 | Standard (UFA) | 4 Years | $5,625,000 | $22,500,000 |
| Ceci, Cody | Toronto Maple Leafs | July 4, 2019 | Standard (RFA) | 1 Year | $4,500,000 | $4,500,000 |
| Kadri, Nazem | Toronto Maple Leafs | July 5, 2015 | Standard (RFA) | 1 Year | $4,100,000 | $4,100,000 |
| Kerfoot, Alexander | Toronto Maple Leafs | July 4, 2019 | Standard (RFA) | 4 Years | $3,500,000 | $14,000,000 |
| Johnsson, Andreas | Toronto Maple Leafs | June 28, 2019 | Standard (RFA) | 4 Years | $3,400,000 | $13,600,000 |
| Kapanen, Kasperi | Toronto Maple Leafs | June 28, 2019 | Standard (RFA) | 3 Years | $3,200,000 | $9,600,000 |
| Matthias, Shawn | Toronto Maple Leafs | July 6, 2015 | Standard (UFA) | 1 Year | $2,300,000 | $2,300,000 |
| Winnik, Daniel | Toronto Maple Leafs | July 1, 2015 | Standard (UFA) | 2 Years | $2,250,000 | $4,500,000 |
| Holl, Justin | Toronto Maple Leafs | December 31, 2019 | Standard (UFA) | 3 Years | $2,000,000 | $6,000,000 |
| Parenteau, Pierre-Alexandre | Toronto Maple Leafs | July 1, 2015 | Standard (UFA) | 1 Year | $1,500,000 | $1,500,000 |
| Carrick, Connor | Toronto Maple Leafs | June 20, 2018 | Standard (RFA) | 1 Year | $1,300,000 | $1,300,000 |
| Engvall, Pierre | Toronto Maple Leafs | February 12, 2020 | Standard (RFA) | 2 Years | $1,250,000 | $2,500,000 |
| Hunwick, Matt | Toronto Maple Leafs | July 1, 2015 | Standard (UFA) | 2 Years | $1,200,000 | $2,400,000 |
| Arcobello, Mark | Toronto Maple Leafs | July 1, 2015 | Standard (UFA) | 1 Year | $1,100,000 | $1,100,000 |
| Pánik, Richard | Toronto Maple Leafs | July 1, 2015 | Standard (RFA) | 1 Year | $975,000 | $975,000 |
| Lindholm, Pär | Toronto Maple Leafs | May 17, 2018 | Entry-Level | 1 Year | $925,000 | $1,775,000 |
| Engvall, Pierre | Toronto Maple Leafs | May 17, 2018 | Entry-Level | 2 Years | $925,000 | $1,850,000 |
| Ozhiganov, Igor | Toronto Maple Leafs | May 17, 2018 | Entry-Level | 1 Year | $925,000 | $1,775,000 |
| Lehtonen, Mikko | Toronto Maple Leafs | May 4, 2020 | Entry-Level | 1 Year | $925,000 | $925,000 |
| Korshkov, Yegor | Toronto Maple Leafs | May 1, 2019 | Entry-Level | 2 Years | $925,000 | $1,850,000 |
| Mikheyev, Ilya | Toronto Maple Leafs | May 6, 2019 | Entry-Level | 1 Year | $925,000 | $925,000 |
| Barabanov, Alexander | Toronto Maple Leafs | April 7, 2020 | Entry-Level | 1 Year | $925,000 | $925,000 |
| Hyman, Zach | Toronto Maple Leafs | June 24, 2015 | Entry-Level | 2 Years | $900,000 | $1,800,000 |
| Sandin, Rasmus | Toronto Maple Leafs | July 15, 2018 | Entry-Level | 3 Years | $894,167 | $2,775,000 |
| Beck, Taylor | Toronto Maple Leafs | July 13, 2015 | Standard (RFA) | 1 Year | $875,000 | $875,000 |
| Dermott, Travis | Toronto Maple Leafs | July 22, 2015 | Entry-Level | 3 Years | $863,333 | $2,775,000 |
| Robertson, Nicholas | Toronto Maple Leafs | September 19, 2019 | Entry-Level | 3 Years | $850,000 | $2,550,000 |
| Abramov, Mikhail | Toronto Maple Leafs | March 10, 2020 | Entry-Level | 3 Years | $810,000 | $2,430,000 |
| Král, Filip | Toronto Maple Leafs | April 1, 2020 | Entry-Level | 3 Years | $810,000 | $2,430,000 |
| Scott, Ian | Toronto Maple Leafs | December 14, 2018 | Entry-Level | 3 Years | $805,833 | $2,825,000 |
| Marincin, Martin | Toronto Maple Leafs | July 1, 2018 | Standard (RFA) | 1 Year | $800,000 | $800,000 |
| Pickard, Calvin | Toronto Maple Leafs | June 20, 2018 | Standard (RFA) | 1 Year | $800,000 | $800,000 |
| Duszak, Joseph | Toronto Maple Leafs | March 13, 2019 | Entry-Level | 2 Years | $800,000 | $1,600,000 |
| Woll, Joseph | Toronto Maple Leafs | March 24, 2019 | Entry-Level | 3 Years | $800,000 | $2,400,000 |
| Hollowell, Mac | Toronto Maple Leafs | March 7, 2019 | Entry-Level | 3 Years | $799,766 | $2,399,300 |
| Kivihalme, Teemu | Toronto Maple Leafs | May 7, 2019 | Entry-Level | 1 Year | $792,500 | $925,000 |
| Johnsson, Andreas | Toronto Maple Leafs | July 13, 2018 | Standard (RFA) | 1 Year | $787,500 | $787,500 |
| Rubins, Kristians | Toronto Maple Leafs | April 1, 2020 | Entry-Level | 2 Years | $785,000 | $1,570,000 |
| Der-Arguchintsev, Semyon | Toronto Maple Leafs | September 21, 2018 | Entry-Level | 3 Years | $783,333 | $2,430,000 |
| Lindgren, Jesper | Toronto Maple Leafs | May 17, 2018 | Entry-Level | 3 Years | $775,833 | $2,775,000 |
| Petan, Nicolas | Toronto Maple Leafs | March 21, 2019 | Standard (RFA) | 2 Years | $775,000 | $1,550,000 |
| Moore, Trevor | Toronto Maple Leafs | January 13, 2019 | Standard (RFA) | 2 Years | $775,000 | $1,550,000 |
| Johnsson, Andreas | Toronto Maple Leafs | June 4, 2015 | Entry-Level | 3 Years | $750,833 | $2,775,000 |
| Shore, Nick | Toronto Maple Leafs | July 1, 2019 | Standard (UFA) | 1 Year | $750,000 | $750,000 |
| Sparks, Garret | Toronto Maple Leafs | March 5, 2019 | Standard (RFA) | 1 Year | $750,000 | $750,000 |
| Rosén, Calle | Toronto Maple Leafs | December 10, 2018 | Standard (RFA) | 2 Years | $750,000 | $1,500,000 |
| Agostino, Kenny | Toronto Maple Leafs | July 1, 2019 | Standard (UFA) | 2 Years | $737,500 | $1,475,000 |
| Wilson, Garrett | Toronto Maple Leafs | July 24, 2019 | Standard (UFA) | 1 Year | $725,000 | $725,000 |
| Brooks, Adam | Toronto Maple Leafs | May 14, 2020 | Standard (RFA) | 2 Years | $725,000 | $1,450,000 |
| Hutchinson, Michael | Toronto Maple Leafs | June 27, 2019 | Standard (UFA) | 1 Year | $700,000 | $700,000 |
| Marincin, Martin | Toronto Maple Leafs | June 29, 2019 | Standard (UFA) | 1 Year | $700,000 | $700,000 |
| Spezza, Jason | Toronto Maple Leafs | July 1, 2019 | 35+ | 1 Year | $700,000 | $700,000 |
| Gravel, Kevin | Toronto Maple Leafs | July 1, 2019 | Standard (UFA) | 1 Year | $700,000 | $700,000 |
| Marincin, Martin | Toronto Maple Leafs | July 9, 2015 | Standard (RFA) | 1 Year | $700,000 | $700,000 |
| Åberg, Pontus | Toronto Maple Leafs | July 24, 2019 | Standard (UFA) | 1 Year | $700,000 | $700,000 |
| Kossila, Kalle | Toronto Maple Leafs | July 24, 2019 | Standard (UFA) | 2 Years | $700,000 | $1,400,000 |
| Gaudet, Tyler | Toronto Maple Leafs | July 24, 2019 | Standard (UFA) | 1 Year | $700,000 | $700,000 |
| Marincin, Martin | Toronto Maple Leafs | January 10, 2020 | Standard (UFA) | 1 Year | $700,000 | $700,000 |
| Borgman, Andreas | Toronto Maple Leafs | March 6, 2019 | Standard (RFA) | 1 Year | $700,000 | $700,000 |
| Holl, Justin | Toronto Maple Leafs | July 3, 2018 | Standard (RFA) | 2 Years | $675,000 | $1,350,000 |
| Kaskisuo, Kasimir | Toronto Maple Leafs | May 29, 2018 | Standard (RFA) | 2 Years | $675,000 | $1,350,000 |
| Brennan, T.J. | Toronto Maple Leafs | June 4, 2015 | Standard (UFA) | 1 Year | $675,000 | $675,000 |
| Gauthier, Frédérik | Toronto Maple Leafs | July 11, 2018 | Standard (RFA) | 2 Years | $675,000 | $1,350,000 |
| Jooris, Josh | Toronto Maple Leafs | July 1, 2018 | Standard (UFA) | 1 Year | $650,000 | $650,000 |
| Ennis, Tyler | Toronto Maple Leafs | July 6, 2018 | Standard (UFA) | 1 Year | $650,000 | $650,000 |
| Subban, Jordan | Toronto Maple Leafs | July 1, 2018 | Standard (UFA) | 1 Year | $650,000 | $650,000 |
| Cracknell, Adam | Toronto Maple Leafs | July 1, 2018 | Standard (UFA) | 1 Year | $650,000 | $650,000 |
| Carrick, Sam | Toronto Maple Leafs | May 28, 2015 | Standard (RFA) | 1 Year | $600,000 | $600,000 |
| Granberg, Petter | Toronto Maple Leafs | June 23, 2015 | Standard (RFA) | 1 Year | $600,000 | $600,000 |
| Froese, Byron | Toronto Maple Leafs | July 3, 2015 | Standard (RFA) | 2 Years | $575,000 | $1,150,000 |
| PLAYER | TEAM | YEAR | ROUND | OVERALL |
|---|
| DATE | TRADE DETAILS | |||||||||||||||||||||||||||||||||
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