HARRISBURG - In less than two years, Gov. Wolf has presided over a state that has legalized medical marijuana, broken the state-run monopoly on the sale of wine, increased funding for public schools, imposed tougher rules on gas drilling, and formally legalized ride-sharing.
Yet, in some ways, Wolf has never been more politically vulnerable.
The first-term Democratic governor is coming off a humbling election that saw his party lose the presidency and turn out disappointing results in congressional and state legislative contests.
And he is about to enter a year when Republicans are poised to pile up bundles of campaign cash to oust him in 2018, even as they command historic majorities in both legislative chambers.
By all accounts, they will have little incentive to help Wolf, whose administration just last week received a gloomy financial reminder that the state could face a nearly $2 billion budget deficit next year.
How Wolf deals with the impending challenges could mark a make-or-break moment for the often reserved and difficult-to-read governor.
Supporters say he will have to break out of his comfort zone to do the type of retail politicking that came more naturally to some of his predecessors, and less time governing behind closed doors.
"Tom Wolf is a nice gentleman, but he's in a real dilemma now," said Rep. Nick Kotik, a conservative Democrat from suburban Pittsburgh who is retiring after serving for more than a decade. "He's got a tough row to hoe."
Wolf was not available for comment late last week, but top aides, both privately and publicly, describe him as dedicated and serious about doing the right thing.
"He is a good governor who works hard at his job - and loves his job," said Mary Isenhour, Wolf's chief of staff, adding: "He's the best boss I've ever had. Every day I have worked for him, I have learned something new."
Wolf's first year in office was dominated by a record-long budget impasse that placed on full display how exacting it would be for him to score policy wins out of the GOP-controlled legislature, with its increasing number of staunchly conservative members.
The last year has been more low-key.
Wolf has shifted many of his public events to outside the Capitol, and veered off the well-tread and politically tricky policy track to advocate on issues over which he has more control, like opioid-abuse prevention and treatment.
He has been less vocal - almost conspicuously so - on the more thorny policy issues of the day, such as reforming the state's pension system for state and public school employees. During the legislature's brief fall session, which just ended, the GOP-led chambers almost single-handedly drove the discussion on such matters.
Wolf seemed largely absent during that time, at least publicly. Aides say he regularly communicated with both Republicans and Democrats.
Senate Minority Leader Jay Costa (D., Allegheny) called Wolf "a hands-on guy." During the budget, he said, the governor would tinker with his own spreadsheets.
"He would sit at his computer and type in the numbers," Costa said.
In an interview Thursday, Senate Majority Leader Jake Corman (R., Centre) said he has had less interaction with the governor since some of the more pressing budget items were resolved.
And he noted that many of the policy wins the administration has touted - including legalizing medical marijuana and expanding alcohol sales - were issues negotiated in the legislature.
Still, Corman and other top Republicans said relations with the Wolf administration have been smoother since it shed some aides the GOP believed were too partisan.
Senate President Pro Tempore Joe Scarnati (R., Jefferson) said next year's budget will be "the real test of his administration."
Though the next six weeks are expected to be quiet - the legislature last week wrapped up its two-year session - the new year will bring with it a new and more heavily Republican legislature and some of the same issues that have strained relations in the Capitol.
Among the first items on the agenda will be to devise a plan to regulate and tax online gambling - a revenue stream Wolf and lawmakers are counting on to help fund this year's budget, which is nearly halfway done.
The next fiscal year looms as an even larger problem.
Last week, the state's Independent Fiscal Office said the state will face a $1.7 billion shortfall in the 2017-18 budget. Given the GOP's aversion to increasing the state sales or income taxes, Wolf and the legislature will again be on a collision course over how to raise new money.
Republicans say political considerations will not color their approach, but they also have their eyes on Wolf's office.
Already, a fiscally conservative and independently wealthy Republican senator from York County, Scott Wagner, has said he intends to run against Wolf in 2018. Other GOP challengers are expected to follow.
As an incumbent with millions of his own, Wolf might be hard to beat.
But many Republicans are eyeing the results of this year's election as a sign that Democrats can no longer win statewide races only by dominating in the more populous, voter-rich areas of Allegheny County and Philadelphia and their suburbs.
Wolf, as the statewide party's titular head, has said he will shoulder some responsibility for Democrats' lack of success at the polls this month.
Some Democrats privately complain he could have done more to help the party stem its losses, including sending more money to local races and being more visible on the campaign trail. Others counter that there was little he could have done to change the course of a historic election that saw President-elect Trump become the first Republican to win Pennsylvania in nearly 30 years.
"It was a national trend, and Pennsylvania was swept up in it," said Tony May, a Harrisburg-area public-relations expert who was a top spokesman to former Govs. Bob Casey and Milton Shapp.
Many Democrats agree on one point: Wolf needs to emerge more often from the confines of his office and blast out his story.
One Democratic strategist who asked not to be identified for fear of alienating the current governor noted that Wolf could learn something from his Republican predecessor.
Gov. Tom Corbett was ousted in part, the strategist said, because he didn't engage voters until too late in his first term, after his policy decisions and budget cuts had eroded the popularity that helped him get elected.
The strategist said Wolf has a good story to tell but "he's going to have to get back in that Jeep of his and get back out there and tell people what he's done."