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NHL.com is providing in-depth analysis for each of its 31 teams throughout August. Today, three questions facing the San Jose Sharks.

Since entering the NHL in 1991-92, the San Jose Sharks have made the Stanley Cup Playoffs in 19 of 25 seasons, won six Pacific Division titles and advanced to the Stanley Cup Final once, in 2016.
All that's missing is the Cup, and it's seemingly becoming harder for the Sharks to win it. What will make this season more challenging is making up for the loss of forward Patrick Marleau, 37, who signed with the Toronto Maple Leafs on July 2 as an unrestricted free agent after 19 seasons in San Jose.
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1. How will they replace Patrick Marleau?

With the departure of Marleau, the Sharks lost 27 goals and 16 power-play points (seven goals, nine assists) after finishing 19th in the NHL in scoring (2.67 goals per game) and 25th on the power play (16.7 percent). The onus to help provide scoring will be on forwards Logan Couture, Mikkel Boedker and Joonas Donskoi.
Couture scored 25 goals last season and hasn't reached 30 since he had 31 in 2011-12. He's also recovering from an injury sustained when he took a puck to the mouth against the Nashville Predators on March 25 that impacted him (two goals, one assist) during the Sharks' six-game loss to the Edmonton Oilers in the Western Conference First Round.
Boedker, who signed a four-year contract with the Sharks on July 1, 2016, had 26 points (10 goals, 16 assists) in 81 games. The Sharks are hoping for a breakout season from Boedker, whose NHL career high of 51 points (19 goals, 32 assists) came with the Phoenix Coyotes in 2013-14.
Donskoi, 25, had 12 points (six goals, six assists) in 24 playoff games in 2016 but underachieved last season with 17 points (six goals, 11 assists) in 61 regular-season games.

2. Can Joe Thornton and Tomas Hertl stay healthy?

Thornton, 38, signed a one-year contract July 2 after playing 79 games last season. He saw his production decline from 82 points (19 goals, 63 assists) in 2015-16 to 50 (seven goals, 43 assists) and had surgery to repair two damaged ligaments in his left knee April 24. Though he's projected to remain the first-line center, Thornton's time there may be numbered if age and durability become issues.
Hertl has 124 points (59 goals, 65 assists) in 249 NHL games, but knee injuries limited him to 49 games last season. He proved capable with 46 points (21 goals, 25 assists) in 81 games in 2015-16 and is another candidate to replace Marleau on the first power-play unit. If Hertl stays healthy, he could surpass 50 points for the first time in his NHL career.

3. Is their window to win the Stanley Cup closed?

The core is getting older and the competition in the Pacific is better. The Anaheim Ducks have won the division each of the past five seasons, the Oilers are on the rise after making the second round of the playoffs, and the Flames improved by trading for defenseman Travis Hamonic and goalie Mike Smith in the offseason. San Jose's window to win the Cup may not be closed, but it's smaller with a roster that has eight players age 30 or older, including three who are 36 or older.
Young forwards
Timo Meier
, 20, and
Kevin Labanc
, 21, who have played a combined 89 NHL games, are reasons for optimism, and each may receive an expanded role after splitting time with the Sharks and the San Jose Barracuda of the American Hockey League last season.