As the clock ticked down toward the deadline, it became abundantly clear that owner Glen Taylor and president of basketball operations David Kahn didn't want to go that far.
So the two sides found a middle ground.
Love signed a four-year maximum extension Wednesday worth more than US$60 million that allows him to opt out after three years.
The deal offers the financial flexibility and protection from injury that the Timberwolves were seeking while giving the 23-year-old Love the freedom to become an unrestricted free agent in 2015 if he so chooses.
"Did I want the five years? Of course," Love said on a conference call from Dallas, where the Timberwolves were facing the Mavericks on Wednesday night. "It was something I felt strongly about. But at the end of the day, a four-year deal is still great."
Under the new collective bargaining agreement, teams can offer one player on their roster a five-year deal with annual raises of 7.5 per cent, which is one year longer and three percentage points higher than any other team can offer.
Love has emerged as the new face of the franchise in the post-Kevin Garnett era, an all-star who led the NBA in rebounding last season and is off to an even better start this year. He is fifth in the NBA in scoring (24.9 points per game), second in rebounding (13.9) and first in minutes (39.4).
"He's the key of this team. He's our leader," point guard Ricky Rubio said. "We appreciate what he does on the court. It's great for us."
Coupled with the additions of coach Rick Adelman and Rubio, Love has helped form a promising foundation. Still, Love can leave if he doesn't like the direction the organization is headed in three years.
"The early termination keeps my options open and I want to see where this team is going to head," Love said. "I feel that we are (on the right track), and that we'll get there. ... I'm looking at this as a four-year deal and we'll go from there."
With this grueling, lockout-shortened season still only a quarter of the way finished, Kahn said he and Taylor felt that extending a player even as accomplished as Love for five years was more than they were comfortable doing.
"In a perfect world, we would have been able to do five years and not have any risk and not leave ourselves vulnerable," Kahn said. "But it's not a perfect world. The main thing is Kevin is a max player and he deserves max money. I'm very pleased for him that he can have financial security that this contract provides."
The team had until 11 p.m. Wednesday to sign Love to a deal and prevent him from becoming a restricted free agent in July. Oklahoma City gave Westbrook a five-year, $80 million deal and Chicago signed Rose to a five-year, $94 million deal under a provision that Rose earned by winning the MVP last season.
"They're in totally different positions," Love said, pointing out that the Thunder and Bulls are both considered championship contenders while the Wolves haven't been to the playoffs since 2004.
Even after all that he accomplished in his first three seasons — the first 30-point, 30-rebound game since 1982, becoming one of the rare big men who can shoot reliably from 3-point range and finally giving the franchise a star player that fans could cheer for after Garnett was traded — there still was some debate entering the season about whether Love deserved a max extension.
Skeptics noted that Love wasn't the kind of player to create his own shot in late-game situations and struggled on the defensive end, which meant that all the gaudy numbers he was piling up rarely led to victories.
But as this season has opened, Love quickly showed that the only debate left about his value to the Timberwolves was the length of the contract. He showed up to training camp 25 pounds lighter and in superb shape, which has served him well.
He's also added a step-back jumper and a turnaround bank shot that allows him to create space between himself and the defender and is improving as a help defender on the other end. He drilled a 27-foot three-pointer at the buzzer to beat the Clippers in Los Angeles and scored 39 points and grabbed 12 rebounds in a loss against Houston on Monday.
The four-year deal gives the Timberwolves some flexibility going forward and keeps that "designated player" five-year option available for Rubio, No. 2 overall pick Derrick Williams or another player down the road.
All three players, and Adelman, could have their contracts up in the summer of 2015.
"It's good to have our centerpiece," Williams said. "We need a guy like him to put up 25 and 10 every night. ... I had a feeling he would stay with the fan base he's built."
Even though his play may not have indicated it, Love said the situation was wearing on him as the deadline approached. He said he was relieved that it was all over and would playing "with a chip on my shoulder" after not getting the five-year deal.
"I understand his position," Kahn said. "It was a very close call. I don't believe, however, that Kevin will be affected by it. I believe that Kevin, deep down, cares about one thing and one thing only, winning. And I think that he understands that, to the extent that this might help us achieve some team objectives, that he's OK with it."
If there was any disappointment about Love settling for a shorter contract, Adelman didn't see it.
"I was hoping for 10 years...for me," the coach deadpanned. "I think he understands. You don't want to be someone who signs a contract and immediately starts complaining. He sees the opportunity. I'm hoping he relaxes a little bit and we can start making him a more complete player."
Freelance writer Amit Kaluskar in Dallas contributed to this report.