At age 37, with 17 NHL seasons under his belt (1305 games played, 555 goals, 766 assist, totaling 1321 points), Mats Sundin seems to be at a crossroads.  

After 83 playoff games—including 35 goals and 39 assists—Sundin still has no Stanley Cup ring.

Spending most of your career with the Toronto Maple Leafs will do that for you.  

Sundin had the chance to be traded to the Detroit Red Wings at the 2008 trade deadline. He declined his chance to play for a Cup contender.  The Red Wings won the Cup, while Sundin sat at home.

Now he's a unrestricted free agent this summer. He currently has offers to play for the Vancouver Canucks (for two years and $20 million), the Montreal Canadiens, and the New York Rangers.

If Sundin wants to win a Cup, he should sign with the Habs.  If he only cares about money, then obviously the Canucks.  If he wants to play on an old worn-out team with big names but little chance of a Cup, he could sign with the Rangers.

Hossa took a discount to play with the Red Wings for one year in hoping of capturing his first Stanley Cup. Maybe Sundin should take note of that. But if Sundin doesn't really want a chance to win a Cup, he'll sign back with the Leafs.

Even with him in their lineup, Toronto is looking at a worse year than last.  It'll be interesting to see where Sundin takes his career as it winds down and the window for a shot at the cup gets smaller and smaller.