Dwane Casey is the all-time winningest coach in Toronto Raptors history.

With Sunday’s 106-87 victory against the Milwaukee Bucks, the Raptors moved to 3-0 on the season while Casey moved to 157-158 as the team’s head coach. His 157th win pushes him past Sam Mitchell on the franchise’s all-time wins list and pushes his winning percentage – also the best mark in franchise history – within one game of .500.

The 3-0 start is the first time a Casey-led Raptors team has opened a season on a three-game winning streak. Last year’s team started 2-1 and picked up steam from there, cruising to a 24-7 mark, while Casey’s prior squads started 6-12, 4-19, and 4-13, working backwards. His first win came in his debut on Dec. 26, 2011, with a 104-96 road victory against the LeBron James-less Cleveland Cavaliers.

On win record: Casey appreciates all of the players who have been here, mentions DeRozan, references Drake + SFTB, says team still building. — Holly MacKenzie (@stackmack) November 2, 2015

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Casey tied Sam Mitchell’s win mark with Friday’s victory against the Boston Celtics, and while he’s downplayed the long-term accomplishment publicly, it’s probably nice to know you’re on your way to being an organization’s “best ever” at something. Where Casey ultimately ranks post-facto will depend a great deal on two related factors: Whether he remains in Toronto beyond 2015-16 and whether he can lead the Raptors to just their second playoff series victory ever. Casey should become the first coach to lead the Raptors to the playoffs in three consecutive seasons, but three consecutive first-round ousters may make it tough for some to give him the nod over the handful of other uninspiring candidates for the mantle of best bench boss.

“I love being here and appreciate being here, but the NBA is about opportunity and I want to do the best I can for this organization,” Casey said ahead of Friday”s game. “In the NBA you’re only as good as your last game. In our business, it’s sad, but nobody appreciates the building, what we started, where we are now. All they remember now is that last game.”

Dwane Casey on being a win away from passing Sam Mitchell: that and 7.50 will get you a drink at Starbucks. #WeTheNorth #rtz — Chris O’Leary (@olearychris) November 1, 2015

That’s never more true than for a coach playing without a contract. General manager Masai Ujiri opted not to extend Casey’s contract this offseason, retaining him on lame-duck status despite protestations from pockets of the fanbase after an embarrassing exit from the postseason. Casey was hired by Ujiri’s predecessor, Bryan Colangelo, and Casey’s job security has been a topic of discussion since the moment Ujiri arrived. It’s generally presumed that a general manager will want “his guy,” but the unexpected success of the Raptors over the last two seasons likely shifted plans, both to tear the team down for a full-scale rebuild and for a change behind the bench. Now Casey’s in limbo, and the direction Ujiri opts to go will hinge almost entirely on how this season plays out.

That’s not an ideal scenario for the coach or the franchise, but given the changes in personnel to a more Casey-preferred core, the overhauling of the defense, and several new assistants, it appears Casey’s probably safe for the season. The franchise has changed coaches mid-season on two occasions in the past, to ill effect. While Ujiri has several assistants who could be considered future head coaching candidates – Nick Nurse, Jesse Murmuys, Andy Greer, and Rex Kalamian, probably in that order – if Ujiri was committed to a change, it probably would have happened in the offseason, with ample time for a new coach to take the team in their own direction. Barring a sustained period of struggle, Casey is probably safe until the summer, when everything will be up for re-evaluation.

Whether Ujiri would risk firing the franchise’s winningest coach coming off of three consecutive playoff berths is a tough question, one that’s a few months premature at this point. Given the franchise’s complete lack of success over 20-plus years,it’s unlikely there’d be any outcry about losing the “best” coach in team history. Sadly .498 is the best clip with which a coach has ever finished his Raptors career. That shouldn’t serve to discredit Casey’s accomplishment any – this is his fifth season with the franchise, and he’s often had odds stacked against him. A sub-.500 winning percentage isn’t great resume fodder – he also went 53-69 as head coach of the Minnesota Timberwolves – but considering what this organization’s history, he looks like Red Auberach, comparatively. And again, there have been some circumstances that make his record a little worse than it may have been otherwise.

Casey was hired in late June of 2011, immediately preceding the NBA lockout. That meant his first training camp was an abbreviated one where the team had all of two preseason games to learn Casey’s preferred system, handcuffing him in making wholesale changes. Further complicating matters in his first season was that general manager Bryan Colangelo has admitted to tanking late in the year, with the Raptors pushing for a better draft pick rather than a few additional wins. That’s not something that happens at the coach level, but Casey was working with less than a full deck. The result was a 23-43 season and, unfortunately, Terrence Ross by way of a lost coin flip instead of, say, a Harrison Barnes (coin flip victory) or Damian Lillard (losing the Ben Uzoh Triple-Double Game against the Nets).

Calls for Casey’s job began in his second season at the helm, as the additions of Kyle Lowry and, later, Rudy Gay were expected to push the team forward. The Raptors instead finished 34-48, and when a cold start followed in 2013-14, Ujiri appeared ready to blow things up. He dealt Bargnani (thank you, based Dolan), he found a home for Gay, and rumors had Lowry on the trading block next.

But the strange 2013-14 season began from there, with the team taking off from the Gay trade onward. In another down year for the Toronto Maple Leafs, the likable and unexpectedly successful Raptors caught the city’s attention, storming to a 48-34 record, their first playoff berth since 2007-08, and a new identity by way of the successful (and reportedly pulled ahead) #WeTheNorth marketing campaign. A tough seven-game loss to the Nets was a disappointing ending, but it was an incredible season overall. It’s never easy to find causality in strange seasons like this, but Casey deserves some credit for meshing a lot of new and disparate parts together to find chemistry, even if there are some who still feel the Raptors should have torn down the core for a full rebuild.

The topic of Casey’s employment is a controversial one at Raptors Republic. Several of our writers (present author excluded) are adamant a change has been needed for some time, while we’ve received plenty of feedback from readers who feel the opposite. Personally, I think people look to assign too much blame or credit to Casey in the high and low times, respectively, and he’s generally been good, not great, in his post. The main concern would be that he’s been out-coached in back-to-back playoff series, but the sweep at the hands of Washington wasn’t a slight scheme adjustment or James Johnson sighting from being a seven-gamer; it was a team-wide embarrassment.

Known for his acumen on the defensive end of the floor, the Raptors have been uneven during Casey’s tenure. The tanking Raptors inexplicably ranked 14th in defensive efficiency, seemingly backing up Casey’s reputation, but the team feel to 22nd, rebounded to 10th, and then fell back to 25th last season. The offense has been less volatile, ranking 29th, 13th, 10th, and fourth, but Casey’s rightfully come under fire for a system that lacks creativity and often relies too heavily on the singular shot-making (or foul-drawing) ability of a small handful of players.

The coming season stands as a major litmus test for Casey. He’s been armed with better defensive weapons and urged to make his scheme more conservative in response, while also losing a couple of his relied-upon shot-makers. If the team can return to an above-average defense without too large a resulting drop-off on the offensive end, the Raptors should find themselves safely back in the first round of the playoffs and better equipped to compete in a series.

Returning to the playoffs would make Casey the first Raptors coach ever to make three playoff appearances, and becoming the second to win a playoff series (Lenny Wilkens is the other) would leave little doubt that the noncompetitive mantle of “best Raptors coach ever” belongs to the Kentucky product. Failing to balance the team’s performance and win a playoff series could see Casey set the franchise mark for wins (he needs one more) and games coached (he needs 32) but lose his job in the offseason.