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HomeHandicappersCaleb Wilfinger

Caleb Wilfinger

Deputy Editor
Google News
Caleb is a Deputy Editor at Pickswise who resides in Upper Manhattan and has spent time in Philadelphia and Washington, D.C. He has been handicapping various sports since 2018, including NFL, NCAAF, NBA, NCAAB, MLB and tennis. The futures market is his favorite to target and he has a passion for sharing his plays with the Pickswise community.
Live Picks 1
Live Parlays 1
Weekly News Articles 3
Location
New York
Favorite Sports
NFL
CFB
NBA
MLB
CBB
Tennis
Favorite Teams
Kansas Jayhawks
Los Angeles Dodgers
New York Giants
New York Knicks
Greatest Betting Win
One of my favorite sports betting memories was certainly in October of 2022, when I successfully cashed a 5-team Round Robin parlay involving games I had already played as straight bets. It involved Penn State catching 16 at home against Ohio State, along with Notre Dame, UCF, Louisville and Baylor all on the money line as underdogs. The Irish and Cardinals took care of business early by crushing their opponents and Penn State hung tough to cover the inflated number against the Buckeyes. Meanwhile UCF pulled out a thriller against Cincinnati, leaving me only a Baylor victory away from a serious 50U profit. Thankfully, the Bears made quick work of Texas Tech in the second half and I was able to watch the 4th quarter with a smile on my face. This was one of three 5-leg Round Robin parlays I cashed during the 2022 college football campaign, as part of what was a terrific season on the gridiron.
Greatest Achievements
Finished with a win rate of 63% in weekly 2022 NCAAF best bets column, highlighted by an 8-0 run to close out championship week and bowl season 25-8 (76%) YRFI/NRFI run from June through August 2023.
Education
Caleb attended Penn State University, where he covered Penn State football and basketball for 3 years (along with many other sports), getting an up close and personal look at the grind of a full collegiate athletics regular season. His two bachelor's degrees were in Journalism & Political Science, with sports journalism as a primary focus. During his senior year, Caleb began moving away from betting casually and turning into a sharper bettor, including creating systems, compiling data for multiple sports, etc.
Experience
5+ years betting experience 3+ years as a sports handicapper 10+ years as a sports journalist Caleb has been betting legally since 2019 but his history with gambling predates that, as he regularly picked NFL games against the spread throughout his college tenure. In 2021, Caleb started handicapping college football games for Pickswise and turned a profit for the season. After moving into a full-time Deputy Editor role in 2022, Caleb has had plenty of success and winners for the site’s users, most notably in college football, NFL and the MLB YRFI/NRFI market.
Favorite betting market / type
Futures and Point Spreads.
Favorite bookmakers
Read More

Caleb's Picks

Point Spread Pick
NY Knicks -5.0(-110)

The NBA playoffs are finally here, and one of the most intriguing series comes in the Eastern Conference between the Atlanta Hawks and New York Knicks. This matchup profiles as one that could be pretty similar to what we saw a season ago in the first round, as the Knicks knocked off the then-upstart Pistons in a competitive 6-game series that featured a couple of wild finishes. Atlanta enters this postseason fresh off an outstanding second half of the campaign, and no team saw their point differential increase more than the Hawks over the course of the last 30 games. However, a lot of that did come against a pretty weak schedule, and this is a much tougher test for a team that doesn’t have much of a veteran presence at key positions. Ultimately, this is a series that should be competitive and feature plenty of interesting basketball, but it’s still a matchup that pretty clearly favors New York. The cream should rise to the top over the course of a 7-game series, and that should start in Game 1 with a win and cover for the Knicks at Madison Square Garden.

Atlanta’s offense should have some avenues for success, particularly when it comes to generating open threes for the likes of Nickeil Alexander-Walker, who excelled against New York in the regular season. However, outside of NAW and some occasional bursts for Jalen Johnson, the Hawks ran into some real problems against Mike Brown’s defense down the stretch. Furthermore, the Knicks are a team that is very comfortable in the 4th quarters of these playoff settings, and it’s hard to overstate just how important that is against a fairly inexperienced team on the other side. From a schematic perspective, Atlanta will certainly look to disrupt Jalen Brunson by blitzing him with its rangy wing defenders in order to get the ball out of his hands in big spots. With that said, when it comes to swinging the ball and generating good looks for his teammates, I’ll certainly trust Brunson to consistently make the right read when it matters. Furthermore, the ancillary pieces on New York (Karl-Anthony Towns, Mikal Bridges, OG Anunoby, etc.) are simply more trustworthy compared to Atlanta’s personnel, which gives the Knicks a significant edge in this one.

If New York is going to start fast at home on Saturday, it will probably do so by at least a couple of possessions. In fact, the vast majority of teams that tend to win games in the NBA playoffs also cover spreads. We are now on a 6-year run of straight up winners covering the spread at nearly an 89% clip, and I see no reason for that to tail off this postseason. With that in mind, I’ll continue to follow this trend and lay a relatively short number with the Knicks in a game where New York should do enough to put away the Hawks in front of its home fans.

Hawks vs Knicks prediction: Knicks -5 available at time of publishing. Playable to Knicks -5.5

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Caleb Wilfinger

Caleb's Parlays

Saturday's NHL parlay
Today
Ottawa Senators
Carolina Hurricanes
OTT Senators @ CAR Hurricanes · Money Line
CAR Hurricanes Win
Our Analysis

The Stanley Cup playoffs get underway on Saturday afternoon as the Carolina Hurricanes will be hosting the Ottawa Senators to lead things off. As winners of the Eastern Conference, the Hurricanes will have the home ice advantage in this series. This is important because they are were tied for the most regular season wins on home ice by any team. Their record at the Lenovo Center this season was 29-10-2. These teams split the regular season series, each winning one game. The Senators are among the most popular picks to pull off a first-round upset. However, I am still worried about their defensive play and goaltending. After all Linus Ullmark went through this season, he finished very strong. If this solid play continues into the playoffs, the Senators stand a real chance to beat the Hurricanes. Ullmark has not been good in the playoffs throughout his career, as he has a 5-10-0 record in 15 starts, with a 3.28 GAA and .885 SVP. The Senators will not be able to score their way through this series as the Hurricanes were the 5th-best defensive team in the league during the regular season, averaging 2.88 goals against per game.

The Hurricanes play a very fast and aggressive forechecking style of game that I think is going to wear down the Senators defense as this series progresses. I expect some nerves in the first game from Ullmark and the Senators, and the veteran lineup of the Hurricanes should be able to capitalize on this. Give me the Hurricanes to get it done in the opening game of the Stanley Cup playoffs.

Senators vs. Hurricanes prediction: Hurricanes ML (-150) available at time of publishing. Playable at that number.

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Minnesota Wild
Dallas Stars
MIN Wild @ DAL Stars · Game Totals
Under 5.5
Our Analysis

The Stanley Cup Playoffs will finally be underway for the Dallas Stars and Minnesota Wild when the puck drops on Saturday afternoon. The Stars have the home ice advantage in this very evenly matched first round matchup and I believe it will help give the Stars an edge. These 2 teams split the regular season series with two wins apiece. Both of these teams are very good on the defensive side of the puck. They both ranked inside the top 5 teams in the NHL for goals against. The Wild ranked fourth, averaging 2.87 goals against per game and the Stars were the second-best team in that category, averaging 2.71 goals against per game. Both starting netminders had impressive regular season numbers, Jesper Wallstedt of the Wild had a 2.62 GAA, while Jake Oettinger for the Stars has a 2.59 GAA.

I expect these teams to ease themselves into the playoffs with a buttoned up defensive first period as neither team will want to be the first to make a mistake. Playoff games are typically lower scoring, and I think that is what we will see in game one between the Stars and Wild. Give me the under in this one.

Wild vs. Stars prediction: Under 5.5 (+105) available at time of publishing. Playable at that number.

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Philadelphia Flyers
Pittsburgh Penguins
PHI Flyers @ PIT Penguins · Money Line
PIT Penguins Win
Our Analysis

The Philadelphia Flyers and Pittsburgh Penguins will begin their best-of-7 first-round series in the Stanley Cup playoffs when they clash in Game 1 in Pittsburgh on Saturday night. Don’t be alarmed by the Penguins’ 3-game losing streak to end the regular season — they had already clinched a playoff spot and home-ice advantage in round 1 prior to that skid. The Pens had previously won 3 in a row before pretty much waving the white flag on the remainder of the regular season. When motivated, this club has been playing good hockey. The Flyers, on the other hand, emptied the tank with a late surge to clinch their first playoff appearance since 2019-20 earlier this week. Although plenty of days off helps, it’s still an advantage for Pittsburgh to have basically rested while Philadelphia was making an emotionally draining push for the playoffs. That’s part of the reason why my Flyers vs Penguins pick is Pittsburgh on the money.

It should also be noted that their split of the 4-game regular-season series hardly tells the real story. The Flyers picked up both of their wins in shootouts; the Pens dominated their 2 victorious contests by a combined 11-4 margin. For those counting, that means (not including shootouts) Pittsburgh outscored Philly by 7 goals in the 4 head-to-head encounters. Sidney Crosby heads into another playoff campaign having recorded multiple assists in 3 of his last 4 outings. In the series opener, I’m backing Crosby and the rest of the Penguins’ veterans to ride their experience to a hard-fought victory over an upstart Flyers squad.

Flyers vs Penguins prediction: Pittsburgh ML (-142) available at time of publishing. Playable to -150.

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Caleb's Analysis