ANN ARBOR — More than five years after signing a landmark seven-year contract that made him one of college football’s highest-paid coaches, Jim Harbaugh and the University of Michigan sit at a crossroads.

Ten days ago, on Jan. 11, Harbaugh began his sixth year at Michigan, which is set to pay him a compensation package in 2020 north of $8 million. That figure is a significant increase from December 2014, when he inked his original deal for a $500,000-a-year salary and $4.5 million in additional compensation.

Michigan tacked on an annual life-insurance policy in August 2016 that included a $2 million premium advance, to be paid to Harbaugh each year through the balance of his contract. Factor in a contract-stipulated 10 percent raise for Harbaugh in January 2018 and you arrive at the $7.5 million figure that’s widely cited these days.

And while a second 10-percent raise for Harbaugh kicked in earlier this month, bringing his pay for 2020 above $8 million, the only reference to a potential renewal is a brief, three-sentence paragraph:

“The parties agree that by December 1, 2021, they will meet and indicate whether they have a mutual interest in negotiating an extension of this Agreement," it says. “Any indication by either party that they do not desire to extend the contract shall not be considered a termination of this contract. Any agreement by the parties to discuss an extension does not operate as a guarantee that the parties will agree to an extension.”

While that sounds nice, that’s typically not how coaching contracts in college football go. The expectations are that talks happen much sooner; head coaches prefer peace of mind when it comes to their job status -- and schools prefer not being blindsided by a departure.

Harbaugh is currently five years in at Michigan, his longest tenure ever, anywhere, as a head coach. He spent three seasons at the University of San Diego before taking a job at Stanford, where he lasted four and moved up to the NFL. In San Francisco, despite reaching the NFC championship game three times, his run lasted four seasons before Michigan came calling.

Michigan, however, is a completely different set of circumstances. He attended school here, played quarterback here, and has family ties to Ann Arbor.

But there’s also the all-important recruiting factor here. Ideally, coaches would prefer walking into the family room of a prospective player with three or four years remaining on his contract. Anything less could create pause from the recruit, and open the door for competing schools to use that against Michigan.

It’s unclear whether Harbaugh, 56, and Michigan athletic director Warde Manuel, who did not hire Harbaugh but has praised him publicly, have started these discussions. Manuel, through a Michigan spokesman, has not returned a request for an interview. But he is on record as saying, as recently as May 2018, that he wants Harbaugh to “retire from this institution.”

“Jim knows how I feel about him,” Manuel said at the time. “We’ve had great conversations and I don’t want him to go anywhere.”

In 2019, Harbaugh’s pay made him the third-highest paid coach in college football, trailing only Clemson’s Dabo Swinney ($9.3 million) and Alabama’s Nick Saban ($8.8 million). Michigan made the decision to invest heavily in its football coach, Harbaugh, to varying degrees of success.

In five seasons at Michigan, Harbaugh is 47-18 -- wining a healthy 72.3 percent of his games, with a nearly identical mark in the Big Ten. But he’s failed to lead his teams to a conference championship or the College Football Playoff; Swinney and Saban have done both, several times.

Also under Harbaugh, Michigan is 0-5 against top rival Ohio State (a stretch of losing that began long before Harbaugh, with the Wolverines having dropped 15 of their last 16 games to the Buckeyes) and 1-4 in bowl games. Besides his overall record itself, perhaps Harbaugh’s biggest on-the-field achievement to date is his 3-2 mark against in-state rival Michigan State.

Which often prompts the question from detractors: Is Harbaugh worth it?

Many administrators and top officials at Michigan still say yes. In 2017-18, the most recent data available from the NCAA, the school’s athletic department generated more than $195 million in revenue. About $125 million of that came from the football program, which continues to sell out home games at Michigan Stadium, receive lucrative payouts from the Big Ten’s TV partners and for licensing agreements.

Michigan largely remains competitive on the field thanks to its top-10 recruiting classes, but remains a step behind the best in the Big Ten and nationally. Harbaugh has a lot to do with that, and has remained out of the NCAA’s watchful eye in an era where schools have been sanctioned, lost scholarships and faced public scrutiny.

Harbaugh’s resume and Manuel’s comments publicly indicate that an extension is coming. It only makes sense given the nature of the situation. Harbaugh truly enjoys being in Ann Arbor and coaching Michigan, and the university is proud to have him.

But one has to wonder what’s taking so long. With less than two years left, the clock is ticking before this thing gets awkward.

Read more on Michigan football:

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Michigan OL pledge flips commitment to Baylor

U-M adds Bob Shoop, Brian Jean-Mary to coaching staff

RB Chris Evans practiced last month, and ‘looked good’

Jim Harbaugh in the dark about Michigan’s next spring trip