If not now, when?

When Jim Harbaugh's Michigan Wolverines headed to Columbus in November 2018 for the annual clash with Urban Meyer and the rival Ohio State Buckeyes, that was the question.

If this Michigan squad―ranked fourth and considered one of the nation's hottest teams―couldn't handle a wobbling Ohio State, when would Harbaugh beat the Buckeyes? After a 62-39 beatdown that dropped his record against Meyer to 0-4, the answer felt like never.

But 10 days later, Meyer suddenly—though not unexpectedly—announced his retirement. That decision is one of the reasons 2019 is loaded with opportunity for Harbaugh to end Michigan's seven-year losing streak to Ohio State.

Michigan's roster is built in Harbaugh's image. He has an experienced, NFL-caliber quarterback, a flashy new coordinator to run an experienced-filled offense and a defense built to reload, and the team's pre-eminent rival is working through a transition from Meyer to Ryan Day.

There are no more excuses like previous teams had until 2018.

In 2015, the Wolverines defied seven-win expectations and ended 10-3. A blowout loss to OSU was disappointing but not worrying. Then in 2016, it was "The Spot." In 2017, a September injury to quarterback Wilton Speight stung the Wolverines late.

Yes, turnovers cost Michigan dearly in 2016, and the lack of an adequate backup doomed the offense in 2017. Those are equally important reasons for the losses, but the excuses are understandable. Subpar inherited roster, questionable call, bad luck.

Things finally started to change last season when Ole Miss transfer Shea Patterson settled the QB spot. Plus, new offensive line coach Ed Warinner developed the best blocking unit yet. Those improvements complemented a consistently elite defense that remained as great as ever.

Until it wasn't.

Ohio State scored 62 points, the most Michigan had ever allowed in regulation. Florida scored 41 in the Peach Bowl. While inexcusable, the rare defensive letdowns were less of a concern than the Wolverines' inability to even threaten that they'd keep up.

Harbaugh realized he needed to overhaul the offense. A more dynamic aerial attack was atop the to-do list, so he hired co-Alabama coordinator Josh Gattis. Though a first-time play-caller, he previously served as the passing game coordinator at Penn State and helped craft a tremendous receiving corps at Alabama.

Whether Gattis is the solution is less meaningful than understanding he is Harbaugh's handpicked guy. This is the coach he believes can move Michigan from possibility to contender.

Even if Justin Fields is eligible for OSU, he'll be a first-time starter stepping in for Heisman Trophy finalist Dwayne Haskins. The Buckeyes also lost Mike Weber, Parris Campbell, Terry McLaurin, Johnnie Dixon and three starting offensive linemen. The defense returns a majority of its production but ranked tied for 72nd in yards per play allowed last year. A jump to the "elite" category is unlikely.

Elsewhere in the division, Penn State is moving into the post-Trace McSorley era. Michigan State will be competent because of its defense but must address an abysmal offense. Indiana, Maryland and Rutgers aren't Big Ten contenders.

Michigan has every reason to win in 2019.

The complicated portion of this discussion is context. Harbaugh is nowhere close to the hot seat, and suggesting the opposite is disingenuous. Yet he's not meeting expectations, either.

Harbaugh has zero Big Ten championships, is winless opposite OSU and is just 2-2 against Michigan State. Failing to win titles while also losing to rivals is a major problem; that's why we're here.

At the same time, the school has its best outlook since the late 1990s. While it's short of where Michigan wants to be, the reality is this program hasn't won a national championship in 22 years. Harbaugh has put the Wolverines just shy of the doorstep twice in four seasons.

Before he arrived, only three of U-M's previous 12 years included double-digit wins. Harbaugh has three in four seasons. Plus, revenue has climbed nearly $30 million in his tenure, per USA Today. The support of the program is, fiscally, at an all-time high.

Job security is not in question. Perception matters; his reputation is at stake.

The most effective way to alter this narrative is to finally beat Ohio State and win a Big Ten crown for a spot in the College Football Playoff. And after what has transpired in the last two months, 2019 has become an opportune moment to flip that script.

Harbaugh built this roster. Patterson is back and preparing to lead a theoretically modernized offense behind a seasoned line with experienced wideouts. Their rival no longer has an all-time great head coach and is revamping the skill positions. The rest of the division is lagging behind.

If not now, when?

All recruiting information via 247Sports. Stats from NCAA.com, cfbstats.com or B/R research. Quotes obtained firsthand unless otherwise noted. Follow Bleacher Report CFB Writer David Kenyon on Twitter @Kenyon19_BR.