And these deals come with byproducts of their own, fallout that affects the Pirates' present and future. Let's take a look at a few of them.
Financial flexibility After packaging two prospects to trade Francisco Liriano and his nearly $18 million in remaining salary, general manager Neal Huntington vowed the Pirates would use that "financial flexibility" to strengthen the club. In signing Freese, Huntington almost immediately put his words into action.
"This is a direct example of having some flexibility, of having some breathing room," Huntington said. "To be able to get creative, maybe to stretch beyond what we normally would be boxed into, it did help a little bit."
The Pirates will have other holes to fill this offseason, however, particularly in the bullpen. The club now has a little more than $59 million committed to players under guaranteed contracts in 2017, with several arbitration-eligible players -- Gerrit Cole chief among them -- due for significant raises.
Who's on third? Jung Ho Kang is on the disabled list with a right shoulder injury. He is currently being investigated by Chicago police -- but has not been charged -- regarding a sexual assault allegation in June. Neither had an impact on the Pirates' decision to keep Freese, Huntington said.
The Bucs still plan on Kang being their regular third baseman next season. Freese will assume the same role they had in mind this spring, Huntington said: backup corner infielder and right-handed bench bat.
Who's on first? Freese has taken well to first base, playing 43 games there as part of a platoon with John Jaso. Prospect Josh Bell, called up for an extended audition, appears to be the future at the position, potentially as soon as next season.
The Pirates are keeping their options open, according to Huntington. If they stick with Jaso next year, he could platoon with Freese. If Bell shows that he's ready over the next six weeks, Freese could back up the rookie.
Why didn't Freese test the market? For one, Freese had a rough experience in free agency last offseason, finding few fits until the Pirates came along in mid-March. But he said that wasn't the biggest factor in his decision to accept an extension.
"If I didn't want to be here, I would've rode into the market and seen what went down," Freese said. "The fact that I came to a team that I fell in love with [and] financially it worked out, let's go."
Age-old question Typically, players decline as they enter their mid-to-late 30s. Freese will turn 34 next April. Why would the Pirates invest in a player during that phase of his career?
"It probably would be a little different if we were expecting him to play 155 games a year for the next two or three years," Huntington said. "In this role, it should allow his legs to stay strong. It should allow to bring the skills he brings to the table to play well off the bench, to play well in a part-time role."
Clubhouse chemistry Hurdle brought up an aspect of this extension many won't appreciate. Freese, already a team leader, can be a little more assertive in that role now that he knows he'll be around a few more years.
How well has Freese taken to that role in the clubhouse? Just ask Andrew McCutchen.
"It's been great," McCutchen told MLB.com last week. "He's that quiet guy that turns into, 'Man, he's the most awesome person.' A lot of people don't know him aside from the baseball player that he is, they give that, 'Is he really?' Yeah, he's awesome."