He has four Stanley Cup rings, and he just signed a four-year contract extension that'll keep him in his general manager's role through the 2017-18 season.
But after watching his rising, young team quickly ushered out of the postseason last spring, and seeing no presumptive favorite in the Eastern Conference this year, he's mulling his next move with Monday's NHL trade deadline looming.
He's reluctant to give up a coveted first-round pick, especially for a spring rental, but he's well aware the value an experienced player — particularly on defense — might provide.
So what will Steve Yzerman do? Or what will Ken Holland do, for that matter?
Because the same description applies to both. And irony aside, it's also a fair question to ask at the moment. Maybe even one each GM is asking himself.
Twenty games remain in the regular season, but Detroit and Tampa Bay seem destined to meet in the first round of the playoffs, unless either manages to catch division-leading Montreal. Regardless, you're probably going to have to get by one or both to get where you want to go, and where the Wings haven't been since 2009, the last time they had a roster with this depth of talent.
All of which means the one-time boss and his former Hall of Fame employee — the presumptive master and his overqualified apprentice — are now bigger rivals than ever before. And it means what one does or doesn't do in the next few days certainly could impact — if not influence — the other.
As Lightning coach Jon Cooper says, "These two organizations mirror each other." And while that's no coincidence, given Yzerman's history in Detroit — both as a player and as an executive — it's worth remembering now. Because as Cooper noted, "results dictate behavior sometimes."
So how will these Cup contenders in the East behave at the deadline? Cautiously, no doubt. That has been Holland's modus operandi, by and large, since the NHL implemented its salary cap in 2005. And it's Yzerman's preference, too, when it comes to the trade deadline, last year's big splash (trading Martin St. Louis for Ryan Callahan and picks) notwithstanding
"In general, I'm not a big fan of giving up premium assets and top high draft picks and top prospects for rentals," Yzerman told the Tampa Bay Times recently. "In our state right now, I don't think it's appropriate. And a player to give that up for is not out there right now."
But since each is searching for the same thing right now — "Everybody's out there looking for defensemen," Cooper said — you can't help but wonder how this'll play out.
Holland has made it clear he's comfortable standing pat, despite Johan Franzen's cloudy future and fresh health concerns with Henrik Zetterberg (concussion) and Kyle Quincey (ankle). There's NHL-ready depth up front, with Teemu Pulkkinen the latest youngster to make his case, and on defense, where rookie Alexey Marchenko finally has added a right-handed shot to the mix.
Likewise, Yzerman's keeping his poker face, publicly counting on a healthy return next month from defenseman Matt Carle — one of a couple players he outbid the Wings for a few years ago — even as he works the phones trying to find veteran blue-line help.
It takes two to tango this time of year, they all say, and as Washington Capitals coach Barry Trotz told reporters Thursday, "There's 30 guys and there's only about eight girls. … There's only going to be like eight or nine guys dancing."
Monday's 11th-hour frenzy probably won't match last year's deadline drama, when 20 trades were made, including one (Marian Gaborik) that might've been the Cup-clincher for the Los Angeles Kings.
But that's largely because several deals already have been made, including another involving the Kings — acquiring Carolina defenseman Andrej Sekera on Wednesday — that likely made life more difficult for GMs like Holland and Yzerman. The Hurricanes pried a first-round pick and a decent prospect away from the Kings in exchange for Sekera, arguably the top rental defenseman on the market. The question now is whether other that ratchets up the price for what's left. And if so, how much?
Specifically, what will Edmonton demand for Jeff Petry, the 27-year-old pending free agent — and Michigan native — they've been shopping? Ditto the other right-shot defensemen reportedly on the block, namely Arizona's Zbynek Michalek and New Jersey's Marek Zidlicky, though the latter also has a no-trade clause.
All three figure to interest Detroit and Tampa — and Montreal — at some level, and keep in mind Yzerman has an extra first-round pick in this June's draft, courtesy of the St. Louis swap.
The Red Wings have made it clear their top prospects, center Dylan Larkin and winger Anthony Mantha, aren't available. That may preclude them from making a bigger hockey deal for a top-four defenseman like Arizona's Keith Yandle, or even Columbus' James Wisniewski. (At this point, I don't see Toronto Dion Phaneuf getting dealt, though desperation dictates behavior, too, and old friend Brendan Shanahan seems intent on cleaning house in Toronto.)
But since Holland has said repeatedly that he's not interested in giving up future assets — high picks or valued prospects — just to add a depth defenseman or spare parts, it doesn't leave much to consider. Except maybe the competition.