Because the overwhelming majority of what follows is conjecture, let’s start first with one thing I know for sure: I’m almost certainly not going to win this bet.

The story of how I found myself on the hook for this particular vice of mine is the common one. I really didn’t care for gambling until I won just often enough to believe I actually knew what I was doing. Ever since then I’ve been fucked. I have made trips to Vegas and gambled well, covering the cost of the trip and wee-small-hours steak and eggs with champagne and come home with cash to spare on more than one occasion. Which is to say that I am, in the eyes of The House, a sucker.

A look at my lifetime ledger in casinos supports this. The most generous reading of my track record would grade me out as a decidedly okay sports bettor. My beloved Dad, compelled to impart fatherly wisdom once he realized what foolhardy boy he’d sired, once laid the truism Bet parlays and sleep in the street on me. It’s good advice that I have largely ignored to my own detriment. Over the years, I have become strangely proud of my ability to hit 6/7 legs of $25 parlay that would have paid my rent, which I suppose is really just a dumb way of me getting comfortable with having twenty-five fewer dollars than I once had.

With all that being said, I’m considering some action on the upcoming 2019 NBA Playoffs, and you, dear reader, are invited to play along at home. Rather than getting into individual game bets (I’m not nearly sharp/stupid enough for that) or some of the more specific props that exist (there are many), what I’m looking at here are playoff series prices. To the uninitiated, that means I’m going to be picking series winners with no specificity on individual games. If the numbers listed behind teams are confusing to you (congratulations, you’re not a degenerate!) they should be read thusly:

The negative sign indicates a favorite, while the number itself represents how much money you would have to put up to win $100. The Houston Rockets, for example, are -300, meaning that you’d have give your bookie three hundred bucks to win a hundred back (along with your initial $300, of course.) The Warriors, who are not going to get beat by the Clippers, are -20,000, so if you want to win 100 bucks by betting the Ws, you’re going to have put up a new Kia to do it.

Positive signs signal an underdog, with the number behind it indicating how much money you’d win on a $100 bet. If the Magic (+750) find a way pull the upset by, I dunno, convincing the Raptors that they’ve somehow snuck LeBron onto the roster and Toronto reflexively melts into a puddle, your $100 bet on Orlando would pay you $750 (and your foresight in making this bet would convince me that you’re Biff from Back to the Future Part II.)

Because each round of the playoffs in the NBA is a best of seven series, the likelihood of an upset is considerably less than single-game playoffs like the NCAA tournament or football. Over the loud and inflamed objections of my teenage self, getting lucky one time happens. It just does. But getting lucky four times out of seven is an entirely different ask, and because of this, the NBA playoffs often unfold without surprise. And because I think I know something about basketball, and because I very much am someone who dabbles in casual sports betting, the following will be a completely asinine explanation of how I’m planning on throwing away good money. I’m not sure if my transparency with knowing that this isn’t going to go well makes anything better, but maybe I’ll be embarrassed enough by publicly attaching my name to such a dumbass bet that I won’t do it anymore.

Maybe.

Photo by Keith Allison via Wikimedia Commons

The Heavy Favorites

Golden State Warriors (-20000) v Los Angeles Clippers (+3000)

Milwaukee Bucks (-2800) v Detroit Pistons (+1100)

Toronto Raptors (-1400) v Orlando Magic (+750)

Golden State, Milwaukee, and Toronto are locks of different kind, but locks nonetheless. There is no money to be made betting on them and a bet against feels an awful lot like setting cash on fire. I’ll tie these three in parlay bets (sorry Dad!) to juice the final number a bit, but there’s really not much to see here.

The Joel Embiid Question and Other Stay-Aways

Philadelphia 76ers (-600) v Brooklyn Nets (+400)

Philadelphia's Monstar Joel Embiid has been nursing a sore knee on and off since the all-star break, limiting him to just 10 games. He was last seen on the court on April 6 and his availability for any or all of Philadelphia’s first round matchup against the Brooklyn Nets is anyone’s guess at this point. Meanwhile, Brooklyn has played its way to darling status this year, as NBA writers are tripping over each other with compliments for their coach and successful former Laker snitch-turned-star D’Angelo Russell.

The idiot in me likes the idea of +400 if the Sixers are without Joel — Ben Simmons can’t shoot! the idiot says. They have no depth! he continues — but if Embiid plays, then the Sixers roll in six games or fewer. The lack of certainty and the degree of impact that lies with Embiid’s health is a red flag that’s big enough that even I can see it. The whole series for me is a stay-away. The Sixers are more talented, even without Jo. I wouldn’t lay -600 on it though, and I wouldn’t gamble taxed dollars on the Nets winning four games out of seven, especially without home court.

Photo by Paul Keleher via Wikimedia Commons

Boston Celtics (-480) v Indiana Pacers (+340)

The Celtics are too big of favorites for me to ever bet on, while the Pacers at +340 is exactly the kind of tasty underdog that I throw good money away on while chasing. Indiana did not curl up and die after Victor Oladipo ruptured his quad in January, going 16-19 without him en route to the 5-seed in the East. Miles Turner is a talented big who plays both ways, and Indy’s defense made a habit of grinding teams into dust over the course of the season. Pair these truths with a long, underwhelming season from the Celtics and a recently injured Marcus Smart and I found myself halfway down the well-trod path of talking myself into it.

Ultimately, I didn’t get all the way there. The Celtics suck, I’m pretty sure of this, but Indiana’s best scoring options are Bojan Bogdanovic and Miles Turner. I would ask you to name a third scorer, but I don’t want anyone to hurt themselves (the Tyreke Evans experiment did not work.) As a rule, defenses get serious in the postseason, and the Celtics have good individual defenders like Jalen Brown and Al Horford that could bother the Pacer pair. I just don’t see how Indy scores enough. Kyrie Irving is the best player in the series by miles. If Dipo were here I would gleefully bet the Pacers. Alas, he is not, so I’ll have to use my first-round winnings (lol) to fade the Celtics in round two.

Houston Rockets (-300) v Utah Jazz (+250)

Houston is the last of the larger favorites, and while it should make for good TV, I don’t care much for the matchup from a gambling perspective. I like both of these teams and would be backing them if they weren’t playing each other. They’ve both played well to close the season, but ultimately this is a pass for me because I just don’t have the stones to take Utah here. James Harden is just too good to lose four times, but -300 isn’t compelling to me to do anything. Houston gets through bloodied, but through nonetheless.

At Long Last Action

Denver Nuggets (-270) v San Antonio Spurs (+220)

Though it will displease the overwhelming majority of Halftime Snackers, a pick that I’m considering is one that goes against the beloved hometown Nuggets. The argument against Denver is that they’re largely an inexperienced group, as Paul Millsap is the only member of the Denver core with significant postseason reps.

There are other nits to pick as well.

Will Barton and Gary Harris both spent much of the year injured and never really looked right when they came back, and Denver’s tremendous bench depth that lessened the blow of those injuries during the regular season will be neutralized some by tighter playoff rotations. Nikola Jokic, who will make his first All-NBA team this year, has spent much of the waning days of the regular season collecting technical fouls and losing his cool. Jamal Murray is an untested lead guard who can run hot and cold. They’re 5-5 in their last 10 games (granted, they were not trying to win all of these games).

The best argument against the Nugs, however, is less about Denver and has more to do with San Antonio. The list of people who have gotten rich betting against Gregg Popovich is nonexistent. If playoff experience is something you value, then the Spurs — with their five championships and twenty-two straight seasons in the playoffs — are your team. San Antonio won two out of three against the Nugs this season, and LaMarcus Aldridge is a skilled enough big to give Jokic trouble.

I don’t think I love committing to San Antonio, but 2/1 odds on Pop figuring it out is pretty tempting.

Portland Trail Blazers (+135) v Oklahoma City Thunder (-155)

Finally, something I can sink my teeth into!

When right, Paul George has been an efficient first scoring option, lockdown defender, and fringy MVP candidate. Russell Westbrook hasn’t done his team in in pursuit of stats (20-20-20 for Nipsey was dope as hell though), and Jerami Grant’s 39% shooting from three has finally opened the floor up with the shooting that OKC has consistently lacked. Steven Adams remains a violent actor in the middle. There were times when the Thunder seemed like the most legitimate danger to the Warriors in the west.

Then PG’s shoulder started barking and the whole thing got awfully wobbly. After ripping off four straight wins in early February, the Thunder went 7-14 and plummeted down the standings. Oklahoma City got right in a hurry, nailing down five wins in a row in April and saving themselves from the 8-seed and a date with Golden State, but the last six weeks exposed the extremes that the Thunder are capable of playing to.

Then there’s Portland, who — despite being the dog according to Vegas — won 53 games and finished third in the West. They have homecourt in the series, Damian Lillard, and seemingly little else. Jusuf Nurkic violently broke his leg a few weeks ago, and C.J. McCollum has missed a lot of time lately with a bum knee. There’s also last year’s ugly sweep against the Pelicans to consider. For a team that’s largely identical to last year’s 3-seeded Blazers, there’s a legitimate question to ask about Portland being a good regular season team but fatally flawed for the playoffs. Lillard and McCollum have their defensive limitations, and finding reliable offensive help for the backcourt duo has been a struggle. Enes Kanter has had to step in for Nurk and he’s a truly horrific defender.

They do have Dame though, and ultimately that’s where I’m laying my money. Lillard is the most offensively explosive player in this series, and while Oklahoma City is going to throw the kitchen sink at him defensively, I think he’s motivated to get last year’s stink off of him. It’s hard to get your due as a guard in the West (ask Mike Conley about it), but Lillard is the best player at the position not named Curry or Harden. Oklahoma City has been too inconsistent to trust, and weren’t exactly a juggernaut offensively even when things were good. I wouldn’t put it past Westbrook to clunk it up for a couple of games, and in a series against a team that shoots the three as well as Rip City does (9th-best in the NBA), I’ll roll the dice that the Blazers get hot. I think it goes seven and the home court comes into play, pushing the edge back to Portland.