After he brought back a former No. 1 pick of the franchise to solidify the blue line, his efforts have been almost strictly limited to forwards. Every one of them offered a major upgrade to the current unit.
He pursued a trade with the biggest talent on the block in Rick Nash (and presumably at least put in a call to the Anaheim Ducks about Bobby Ryan) until it became clear that they really did expect Logan Couture in return.
(I add this digression because it is worth re-stating—that asking price is insane. I would rather have Logan Couture right now. Couture was already almost as good last season and will improve more in his third season from age 23 to 24 than Nash will in his 10th season between 27 and 28. Nash will get more goals and points, but Couture will kill penalties and carry an otherwise pedestrian second line.)
At the moment, the Sharks seem to be hoping to add Shane Doan to their roster. But since he is likely to wind up being another player out of their reach, they might want to add a little insurance for the checking lines.
Right now, there is less forward depth to draw upon than last season. A half dozen forwards that suited up a collective 340 games for San Jose last year are no longer under contract, and only one marginal third-line forward signed to replace them.
At 31, Winchester offers experience without worry of a decline. He could easily be signed for under $1 million, with as short or long a contract as the team needs.
The Big Gun provided more than just a big body for the fourth line, with the second-most penalty minutes and hits per minute. He skated well for a big man and added six goals and 10 points in 67 games.
He defends his teammates and the opposition. When the team added enough depth to push him out of the everyday lineup, they were in first place and looked like they had a better chance to earn the top seed than be caught for the Pacific Division title.
But there is a reason the team has shown no interest. He may provide no upgrade over any of the younger forwards projected to suit up daily, and not even much over the seven forwards with NHL experience behind them.
Dominic Moore's situation is different. He was absolutely terrible with the Sharks, but presumably it was because he was preoccupied with his wife's health.
Until they are past that, he will not actively look for a new contract. But if he is available before the season starts, he could help the third line.
He is not yet 32 and was having a good season in Tampa (23 points in 56 games) before the trade. Thus, it is far more reasonable to believe that his struggles were emotional rather than physical. He is a better skater and defender than The Big Gun, yet still physically tough to play against (an oft-stated priority for Wilson) despite his smaller stature (6'0" 192 lbs).
If he returns to the 30-point, elite penalty-killing form he had until February of 2012, Moore could be the team's seventh-best forward. He could possibly even fill in adequately on the second line in the event of an injury.
Every team would be wise to have their roster set without Moore, because he may not even play. For that reason, he would likely come cheap. On some level, he would probably like to redeem his bad season for San Jose, and could be almost as good as other options available (the link being to the best of free-agent profiles at the San Jose Sharks Examiner).