Last year the second round of the NBA Playoffs is where I made hay. I picked the underdog Celtics to beat the 76ers, the (for some reason) underdog Cavaliers to beat the Raptors, as well as the Warriors and Rockets — who were each massive favorites that affected the betting slip by only a tiny degree. When all was said and done I won all four series’, and relatively easily, at that, and the parlay paid out a little less than 11-to-1.
This year betting on the underdogs in Round Two didn’t work out so well. After winning on the road in Game One the Celtics (+250) got manhandled by the Bucks in the next four games, making my logic for picking them look ridiculous in retrospect. From two weeks ago:
The bet here is that the Celtics don’t really give a shit about the regular season, that they weren’t all that worried about having to face the Bucks in the second round, and that they will circle the wagons once the games take on more significance. If I am wrong, then there is every opportunity — or likelihood, even — for the Bucks to take this series down in 5 or 6 games, and for Kyrie to sign a max deal with a team like the Knicks this offseason.
I was wrong and fooled once again. My logic failed, my intuition failed, and ultimately my two-team Eastern Conference Second Round Underdogs parlay failed.
The second leg of that parlay stood a chance. The 76ers (+240) and Raptors did indeed take their series the distance — as predicted — only to be capped off by an all-time ultra-dramatic buzzer-beater by Raptors forward Kawhi Leonard. In a way I was happy that Kawhi hit the shot to give Toronto the series win, because had Philadelphia pulled it out I would have been kicking myself for having the audacity to pick Boston. In other words: my parlay already lost (because of the Celtics), so it didn’t matter whether I was right or wrong about the 76ers.
The Western Conference had a couple good-to-great series’ of their own, with the Blazers beating the Nuggets in 7 games and the Kevin Durant-less Warriors clinching their series on the road in Game 6. I don’t have much to say about James Harden and the Rockets since I expected them to lose in 6 games, anyway, but they have to be kicking themselves that for the second year in a row they had a golden opportunity to upset the best team in basketball, and probably the history of basketball, and ended up with the short stick.
Here’s a review of my second round picks (with winners highlighted in bold):
Warriors > Rockets in 6 games (actually Warriors in 6)
Nuggets > Trail Blazers in 6 games (actually Trail Blazers in 7)
Celtics > Bucks in 6 games (actually Bucks in 5)
76ers > Raptors in 7 games (actually Raptors in 7)
The one truly egregious selection I made was the Celtics; every other series was at least competitive. Nonetheless, a 1-3 second round is far from my best work, making me a pedestrian 8-4 on the series moneyline during this playoff session. That’s even less impressive when you consider just how heavy the favorites were during the first round, especially in the Eastern Conference.
But now that we’re here, it’s not like any of us should be surprised. The Western Conference Finals features the #1 seed and #3 seed, and the Eastern Conference has both the #1 and #2 seed. I think it would have been more fun had it been Warriors/Thunder, and 76ers/Celtics, but that’s more my ego talking than anything else. I don’t care what everyone else wants; I only wanted to be proven right.
With that said, here’s what I got for the Conference Finals:
 Warriors (-550) over  Trail Blazers (+375) in 6 games
With or without Kevin Durant — and I guess he isn’t supposed to play in either of the first two games — I don’t think this is an especially exciting series. Where the Blazers are strong, with Damion Lilliard and C.J. McCollum in the back court, the Warriors are also strong (with Steph Curry and Klay Thompson). Where the Blazers are weak, in the paint, the Warriors have a ton of capable bodies.
Lilliard and McCollum have been special during these playoffs, and seeing them pick off a couple games is expected. If and when there is any sort of game pressure, though, where the game is up for grabs, I’m not going to bet on anyone other than Golden State. They showed their resolve in Game 5 against the Rockets after Durant went down, and they showed it again in the 4th quarter of Game 6. This is the best team in the league, and this series shouldn’t be very dramatic.
 Toronto Raptors (+235) over  Milwaukee Bucks (-290) in 7 games
Everybody is on the Bucks, and everybody has good reason to be on the Bucks. They have been the most impressive team in the NBA all season, as well as the playoffs.
This pick is contrarian, of course, but it’s more to do with just how good a value the Raptors are to bet on. I’ve been making comparisons to the stock market throughout these playoffs, and it’s through that lens that I think betters are getting good value with Toronto.